Is Trump a Great Deal-Maker? Advanced AI Analysis of His Business & Presidential Record
I let AI (o1-pro + deep research) decide with an objective analysis. You can decide for yourself.
Because Trump supporters are hyping up his recent 90 day tariff pause as “genius Art-of-the-Deal dealmaking” I wanted to objectively analyze whether he’s actually skilled at making good deals.
Many love to claim he’s an elite “dealmaker” but they don’t actually reference any of his deals… just cite “Art of the Deal” (a book with unknown reliability that may embellish his dealmaking abilities).
Ask someone what great deals Trump has done and most have no idea.
The truth is that Trump likely deserves credit for securing a subset of good deals in: (A) business AND (B) politics (during his first presidency), both: (1) directly: as a result of high personal involvement & (2) indirectly: as a result of coming up with a smart idea and/or assembling the right team to execute (a skill in its own right).
That said, Trump has taken some hard hits… some of his business dealings backfired or ended up complete flops (this is somewhat expected when you do a lot of deals though).
Furthermore, some portray Trump as the mastermind and/or the elite negotiator in specific great deals he’s been affiliated with — when in reality he was negligibly involved (e.g. the Abraham Accords — a strategic masterclass by Jared Kushner with minimal direct involvement from Trump).
These days in the Trump 2.0 presidency, Trump most likely delegates specific deals he wants negotiated to his underlings (i.e. minions)… then chimes in for negotiations if he feels like it… and hams it up with: PR/media, schmoozing, paperwork, and social media marketing (especially if a deal goes through).
Based on my research, Trump is a bit of a “mixed bag” as a dealmaker. He clearly loves being involved in the deal-making process and admits that deals energize him/fire him up. He’s had some big wins and some big losses.
My biggest takeaway:
Trump is arguably THE BEST IN THE WORLD at: (1) marketing his deals as massive wins (even if they weren’t) & (2) portraying himself as “the best dealmaker” ever. Social media marketing and branding are where Trump wins.
Since I was genuinely curious about Trump’s dealmaking abilities and wanted to eliminate as much bias in analysis as possible… I consulted AI (ChatGPT’s o1-pro + deep research) to analyze Trump’s dealmaking history both in business and politics (as POTUS) — in attempt to objectively gauge his skill at “deal making.”
Read below to see what it came up with.
I.) Timeline of Trump’s Business Deals (1970s to 2000s)
1970s – Early 1980s: Manhattan Real Estate
Donald Trump began in his father’s outer-borough housing business, then moved to Manhattan to pursue bigger projects. (Business Career of Donald Trump)
His first major deal was the Commodore Hotel redevelopment (1978).
Trump partnered with the Hyatt hotel chain to buy the rundown Commodore next to Grand Central Terminal and transform it into the Grand Hyatt New York.
He secured a 40-year tax abatement from New York City – a critical concession that made the financing viable.
Trump’s father, Fred Trump, quietly helped guarantee loans and provided a $1 million loan to keep the project afloat.
The hotel opened in 1980 to great fanfare, burnishing Trump’s reputation as a rising deal-maker.
Given Trump’s personal lobbying of city officials and reliance on family backing, this deal showed Trump’s bold vision and use of connections, but it was also propped up by others’ support.
The Grand Hyatt proved successful, suggesting the deal was substantively beneficial (revitalizing a blighted property) and not just hype.
1983: Trump Tower Completion
In 1983, Trump finished Trump Tower on Fifth Avenue—his flagship skyscraper.
This project required complex negotiations to acquire the Bonwit Teller department store site, purchase air rights from adjacent properties, and navigate city permits.
Trump personally orchestrated these negotiations, demonstrating hands-on involvement in the deal-making phase.
The result was an iconic 58-story tower that sold its luxury condos quickly and became a tourist attraction.
The substance matched the marketing – Trump Tower was a genuine financial success and cemented his image as a bold developer.
Trump’s strategy of “thinking big” was evident here, and he personally oversaw details from design glitz to public relations (famously even demolishing Art Deco friezes he had promised to preserve, drawing publicity).
This early success showed real negotiation skill in assembling property rights and delivering a profitable project.
Mid-1980s: Casino Ventures in Atlantic City
Trump expanded into casinos, but these deals had mixed outcomes.
In 1984, he opened Harrah’s at Trump Plaza, a casino hotel in Atlantic City financed and initially managed by Holiday Corporation (Harrah’s).
Trump built the property, while Harrah’s ran the casino – indicating he had partners shouldering operational duties.
The venture underperformed, leading to tensions with Holiday Corp. Trump soon bought out his partner’s stake, renaming it Trump Plaza, but the casino continued to struggle financially.
In 1985, he acquired another failing casino project from Hilton for $320 million and opened it as Trump Castle, managed by his then-wife Ivana.
Around the same time, Trump purchased the Mar-a-Lago estate in Florida (1985) for use as a private club and personal retreat.
These deals show Trump’s hands-on role in financing and rebranding properties, but also that he often delegated daily management (to Harrah’s, to Ivana, etc.).
The substantive success of these casinos is debatable – while Trump marketed them as part of his growing empire, the Atlantic City market was weakening, and profits fell short.
Trump’s pattern was to take on heavy debt and then promote the properties heavily; the long-term benefits were questionable, as several would soon face financial distress.
1986: Wollman Rink Renovation
A smaller but highly publicized deal was Trump’s rescue of Central Park’s Wollman Skating Rink.
After New York City officials spent 6 years failing to renovate the popular ice rink, Trump convinced the city in 1986 to let him take over as contractor.
He promised to finish in 6 months and under budget (delivered in just 4 months (by late 1986) at $775,000 under budget).
Trump hired competent contractors and even a Canadian rink manufacturer, demonstrating practical project management.
He ran the rink for a short period and donated profits to charity in exchange for future concession rights.
This episode was a genuine triumph: the rink reopened quickly to the public’s delight, showcasing Trump’s ability to “deliver the goods” as he promised.
However, it was also masterful marketing. Trump staged numerous press conferences during construction and emblazoned his name on everything from the Zamboni to the rental skates.
As one journalist noted, the “Wollman success” became “the stuff of a carefully crafted, self-promotional legend.” In other words, Trump leveraged a real accomplishment to maximum PR effect – a hallmark of his deal-making style.
Late 1980s – Early 1990s: Overleveraging & Bankruptcies
Trump’s aggressive expansion led to serious financial troubles by the early 1990s. In 1988, he bought New York’s Plaza Hotel for over $400 million, an extremely high price. He openly admitted he “fell in love” with the Plaza, suggesting emotion overtook business sense.
The hotel failed to generate enough revenue to cover its debt, and by 1992, it went into a pre-packaged bankruptcy.
Trump gave up a majority stake to lenders while remaining a figurehead—a deal to restructure debt at the cost of his ownership.
Also in 1988, Trump acquired the unfinished Taj Mahal Casino in Atlantic City (in a complex deal involving investor Merv Griffin).
He opened the Taj Mahal in 1990 as the world’s most expensive casino (over $1.1 billion in costs), financing it largely with junk bonds carrying high interest.
The deal was marketed as the crown jewel of his casino empire—Trump called it the Eighth Wonder of the World—but it was not substantively sustainable.
Within a year (1991), the Taj Mahal went bankrupt, unable to pay its debts. Trump negotiated a restructuring deal with bondholders: he ceded 50% ownership of the casino in exchange for lower interest rates and more time to pay off the debt.
He also had to sell off personal assets like his Trump Shuttle airline and megayacht to appease creditors.
Around the same time, his other Atlantic City casinos (Trump Plaza and Trump Castle) and even his prized Plaza Hotel in NYC all ended up in bankruptcy or debt workouts by 1992.
In total, 6 Trump business entities declared Chapter 11 bankruptcy between 1991 and 2009. Trump never declared personal bankruptcy, but he repeatedly used Chapter 11 as a tool to negotiate better terms with banks and bondholders when his ventures couldn’t pay debts.
As Trump later said:
“I do play with the bankruptcy laws – they’re very good for me… We’ll have the company, we’ll throw it into a chapter, we’ll negotiate with the banks. We’ll make a fantastic deal.”
This quote illustrates that Trump viewed renegotiating debt as just another deal-making tactic – using legal leverage to force creditors into a settlement.
In these early-90s deals, Trump’s personal involvement was often about brinkmanship with lenders: he convinced banks that letting him reorganize was better than forcing liquidation.
He personally met with bankers and used his celebrity and bravado to argue he was more valuable alive than dead (famously, banks even extended him personal living credit to prevent a complete collapse of his empire).
The outcomes, however, were mixed – while Trump preserved a role for himself, he lost significant equity in his properties.
These episodes reveal limits in Trump’s deal-making: His bold risk-taking led to collapse, and while he negotiated his way out, the underlying deals were far from the big wins he projected. In essence, he overstated successes (the grand casinos) and then used tough negotiation to minimize his losses when reality hit.
Mid-1990s: Rebuilding & Savvy Deals
Having learned from the debt debacle, Trump shifted strategy in the mid-1990s.
Notably, he executed a savvy real estate play with 40 Wall Street (1995–1996).
He acquired the vacant 70-story Manhattan office tower for a relatively low price — around $1 million annual lease with an option to buy.
He invested in renovations, reportedly putting in very little of his own money (approximately $15–20 million) while financing the rest.
Within a few years, the New York real estate market boomed.
In 2003, Trump and his partners sold the building (now called The Trump Building at 40 Wall) for $1.4 billion — then a record price for an office tower in North America.
This deal was highly beneficial: Trump turned a modest investment into a massive profit by timing the market and using other people’s money. It reflected a shrewder Trump, one who protected his downside (minimal equity at risk) while maximizing upside potential.
In 1998, Trump made a similar move:
He partnered to purchase Manhattan’s landmark General Motors Building for $878 million.
Again, he contributed little cash upfront, then sold it in 2003 for a hefty profit.
During this period:
Trump’s personal involvement often meant finding investment partners and leveraging his brand, not risking his own capital.
He focused on brand value and deal structure, rather than direct management or high personal exposure.
These late-90s deals demonstrate genuine negotiating skill. Trump:
Capitalized on market cycles
Struck profitable partnerships
Used strategic branding to enhance deal appeal
They also marked a turning point: Trump increasingly positioned himself as a marketable brand, not just a traditional investor or builder.
2000s: The Trump Brand & Licensing Deals
Trump’s deal-making in the 2000s extended well beyond owning physical properties. Thanks to the success of his reality TV show The Apprentice (from 2004) and a wave of revived fame, Trump realized he could make substantial money by licensing his name.
Many developers began paying Trump for the use of his name and image on buildings — essentially branding deals where he often had no equity stake.
Towers in Istanbul, Manila, and Vancouver carry the Trump name but were financed and owned by local partners; Trump’s company collected fees or royalties in return.
According to Forbes, by the mid-2010s, this licensing business — run largely by his children — was the most valuable part of his empire, valued at over $500 million.
Trump also lent his name to various products, such as:
Trump Steaks
Trump University seminars
Other Trump branded merchandise
These had mixed success. The underlying strategy in these deals was clear: low risk, high reward.
Trump invested little to no capital but charged for brand usage — demonstrating savvy contract-making based on celebrity leverage.
However, the substance of some ventures was questionable:
Trump University (launched 2005) was a real estate seminar program that ended in lawsuits alleging fraud. Trump settled for $25 million in 2016.
His involvement was mostly limited to branding — he didn’t design the courses or teach — which led to quality control issues.
Still, the proliferation of Trump-branded buildings demonstrated a shrewd understanding of licensing leverage:
Local partners often gained financing or boosted sales due to the Trump name.
Trump profited with minimal involvement.
But as Trump’s political profile rose, the model began to show cracks:
By 2015–2016, amid the controversy of his presidential campaign, some partners dropped the Trump name.
The value of his brand reportedly fell sharply.
Trump’s 2000s deals were less about real estate substance and more about marketing, optics, and self-promotion. He mastered the "art of the deal" in publicity, even if he didn’t always deliver value to consumers.
These deals also highlight his reliance on legal teams and staff to finalize contracts while he focused on media visibility — and his tendency to overstate his involvement, often portraying symbolic roles as personal triumphs.
II.) Trump’s Deals as President of the U.S. (2017-2021)
Trump brought his deal-maker branding to the White House, promising to apply his negotiation prowess to trade agreements, peace accords, and legislation. His presidential term offers a mixed ledger of “deals”.
USMCA (NAFTA Renegotiation, 2018–2020)
Trump campaigned on replacing NAFTA, calling it “the worst trade deal ever.” Soon after taking office, he initiated talks with Canada and Mexico to renegotiate the agreement.
The result was the United States–Mexico–Canada Agreement (USMCA), signed in late 2018 and revised in 2019.
Trump publicly celebrated the deal as a major modernization of NAFTA.
However, trade experts note that:
USMCA is very similar to NAFTA, making only modest, mostly cosmetic changes. Many provisions were simply carried over, with updates in areas like:
Digital trade
Slightly stricter automotive rules of origin
The economic impact is expected to be minor. An IMF analysis projected the deal would have a “negligible” effect on GDP.
In terms of substance, USMCA wasn’t a game-changer, though it did include some incremental improvements, such as:
Marginally better access to Canadian dairy markets
Updated digital commerce rules
Trump’s personal role in USMCA was primarily as the instigator and public face of the deal:
He applied pressure by threatening to terminate NAFTA outright.
He imposed tariffs as leverage to push negotiations forward.
He used a “walk away” strategy to compel concessions.
The detailed negotiations, however, were largely handled by:
U.S. Trade Representative Robert Lighthizer
Other career trade officials
Lighthizer conducted multiple rounds of talks with Canadian and Mexican negotiators, often working behind the scenes while Trump tweeted, postured, and made public demands.
The final agreement:
Passed with bipartisan support in Congress
Included additional labor and enforcement provisions pushed by Democrats
Trump’s use of hardball threats showed some negotiating instinct.
However, the modest substance implies he either: (1) Settled pragmatically for what was achievable, or (2) Oversold the results to the public for political gain.
Assessment: USMCA was a real deal — it did formally replace NAFTA — but the outcome was far more modest than Trump’s messaging suggested.
China “Phase One” Trade Deal (2020)
After waging a prolonged tariff war, Trump signed a partial trade agreement with China in January 2020.
China committed to increase purchases of U.S. goods by an estimated $200 billion over two years. It also made limited concessions on:
Intellectual property protections
Financial services market access
In exchange, the U.S. paused further tariff hikes, though most existing tariffs remained in place.
The deal was negotiated primarily by:
U.S. Trade Representative Robert Lighthizer
Treasury Secretary Steven Mnuchin
Trump’s direct involvement included:
Setting the aggressive tone of negotiations
Authorizing tariffs as leverage
Personally meeting China’s vice premier for the signing ceremony
Trump touted the agreement as “a great deal,” but critics highlighted key shortcomings.
It failed to address structural issues such as:
Industrial subsidies
Cyber theft
A proposed Phase 2 deal — which was supposed to resolve deeper issues — never materialized.
The results were underwhelming:
China fell short of its promised purchase targets, especially after the COVID-19 pandemic disrupted global trade.
U.S.–China relations remained tense, and the core strategic disagreements persisted.
Trump’s strategy of using tariffs as negotiating leverage showed a willingness to break norms.
However, the final outcome was limited in scope and effect.
Personal involvement vs. delegation:
Trump acted as the CEO-type figure — setting broad goals, delivering soundbites, and shaping the tone of confrontation.
The fine-print bargaining was handled by seasoned trade officials, echoing a leadership style where delegation drives execution.
Assessment: The Phase One deal amounted to a temporary trade truce rather than a comprehensive reset.
Korea & Others: Limited Trade Progress Beyond USMCA & China
Trump also renegotiated the U.S.–South Korea free trade agreement (KORUS) in 2018.
The changes were relatively minor: South Korea agreed to raise U.S. auto import quotas and extend the phase-out period for U.S. truck tariffs. Trump claimed a big win, though many viewed it as little more than tweaks to an existing deal rather than a true overhaul.
Beyond KORUS, Trump did NOT secure new comprehensive trade agreements with the European Union or the United Kingdom. Talks were initiated, but no formal deals were completed during his term.
In terms of negotiation style, Trump preferred direct, leader-to-leader engagement—often opting for one-on-one summitry or phone calls to push trade issues—while delegating formal negotiations to his staff and trade teams.
For instance, he frequently met or called leaders from Japan and Europe to complain about trade imbalances, but no major “Trump trade deal” emerged in those cases.
Assessment: This phase of Trump’s trade policy was defined more by symbolic diplomacy and personal outreach than by substantive new agreements. While he achieved some revisions to existing deals, his efforts did not yield transformative outcomes with key allies.
The Abraham Accords (2020)
One of Trump’s signature foreign policy achievements was brokering normalization agreements between Israel and several Arab/Muslim states.
In August–September 2020, the UAE and Bahrain formally established diplomatic relations with Israel in what were dubbed the Abraham Accords, signed at the White House.
These were the first Arab-Israeli peace deals since 1994, a historic breakthrough ending decades of those states’ boycott of Israel.
Later in 2020, Sudan and Morocco reached similar agreements with Israel. Morocco’s deal involved U.S. recognition of its claim over Western Sahara.
Substantively, these deals were significant:
They opened travel and trade, security cooperation, and people-to-people ties between Israel and the Gulf states.
The agreements helped rearrange Middle East alliances, especially around shared concerns over Iran.
Unlike some of Trump’s other deals, the Accords had clear, tangible benefits for the parties involved and were not merely cosmetic.
In terms of Trump’s personal role, much of the legwork was done by his advisors— notably Jared Kushner (his son-in-law and senior adviser) and envoy Avi Berkowitz.
Kushner and his team spent months in quiet negotiations with the UAE, Bahrain, and others, facilitated by regional dynamics and an initial proposal to halt Israeli West Bank annexation.
After the UAE deal was set, Bahrain’s leaders phoned Kushner saying “We want to be next,” leading Kushner and Berkowitz to shuttle between capitals and close the Bahrain deal via a conference call between Trump, Israel’s Netanyahu, and Bahrain’s King.
Similarly, the Morocco deal was negotiated by Kushner and Berkowitz as their fourth such agreement in four months.
Trump’s contribution was crucial in a high-level sense:
He green-lit the diplomatic push
Phoned leaders at key moments
Hosted the signing ceremony with great fanfare
His status as U.S. President provided key incentives and guarantees to close the deals—such as arms sales to the UAE or removing Sudan from the terror list.
In effect, Trump largely acted as the closer and public presenter, while specialists handled the intricate discussions.
He adhered to his familiar Art of the Deal showmanship:
Striking an optimistic tone
Basking in photo-ops from the White House balcony
Dubbing the accords as “peace deals” his predecessors couldn’t achieve
Assessment: The Abraham Accords were real diplomatic achievements—but they also highlight how much Trump relied on skilled envoys to negotiate the specifics. His strength in this case was setting the vision, backing it politically, and closing the deals with a flair for theatrics.
Negotiations with North Korea (2018–2019)
Trump took a highly unorthodox approach to addressing North Korea’s nuclear threat — engaging directly with Kim Jong-un through leader-to-leader summits.
In 2018 and 2019, Trump met Kim in Singapore and Hanoi, aiming to strike a “big deal” for North Korean denuclearization.
Trump’s personal style was on full display:
He flattered Kim
Made dramatic gestures, including a symbolic step into North Korea at the DMZ
Spoke of “falling in love” through personal letters
However, despite the unprecedented visuals, no concrete disarmament deal was reached.
The Singapore summit produced only a vague statement of intent.
The Hanoi summit collapsed with no agreement once it became clear that North Korea wouldn’t give up its arsenal without major sanctions relief.
Trump deviated sharply from diplomatic norms:
Previous presidents avoided rewarding North Korea with summits unless there was progress at the working level.
Trump’s gamble was that personal chemistry and his deal-making charm could succeed where traditional diplomacy had failed.
The outcome suggests personal involvement alone was not enough:
Working-level negotiations stalled
North Korea retained its nuclear capabilities
Trump’s strategy — “think big” and “use your leverage” — involved applying maximum pressure via sanctions to bring Kim to the table.
That part worked — Kim engaged
But critics argue Trump lacked preparation, technical groundwork, and a Plan B, which led to the collapse of negotiations
Assessment: The North Korea venture demonstrates that while Trump is willing to go bold, break precedent, and engage directly — an element of ice-breaking negotiation skill — he did not secure a beneficial deal, and talks later languished without substantive progress.
The Taliban Peace Deal (2020)
In February 2020, the Trump administration reached an agreement with the Taliban to wind down the war in Afghanistan.
The Doha Agreement called for the withdrawal of all U.S. and NATO troops by May 2021, in exchange for Taliban promises to cut ties with terrorist groups and begin intra-Afghan peace talks.
This was arguably a high-stakes deal, aimed at ending America’s longest war. However, it was widely viewed as favoring the Taliban’s terms.
The Afghan government was excluded from the negotiations at the Taliban’s insistence, weakening the legitimacy of the talks.
Trump’s role in the deal was primarily high-level:
He approved the framework
Bragged publicly about “bringing our troops home”
Left the actual negotiations to his envoy, Zalmay Khalilzad
Substantively, the deal drew heavy criticism:
It secured few tangible concessions from the Taliban beyond vague counter-terrorism pledges
Contained secret annexes not publicly disclosed
Included a controversial provision: the U.S. pressured the Afghan government to release 5,000 Taliban prisoners, undermining its leverage
Following the agreement:
Taliban violence against Afghan forces increased
The Afghan state rapidly unraveled once U.S. troops began withdrawing
A U.S. watchdog report later concluded the deal was one of the key catalysts for the collapse of the Afghan military
Critics argued that the Trump administration had effectively “appeased” the Taliban, prioritizing a quick exit over sustainable peace. The agreement was seen as undermining a U.S. ally in favor of optics.
In terms of Trump’s deal-making profile:
He was eager to claim credit for ending the war
The heavy lifting and concessions were handled by negotiators like Khalilzad
Trump showed little interest in long-term power-sharing solutions or Afghanistan’s political stability
Assessment: The Taliban deal was marketed as a peace plan, but its tangible benefit is highly questionable given the Taliban’s swift takeover after U.S. withdrawal. It reflects a pattern where Trump prioritized the appearance of a deal—and the short-term political credit—over a robust, enforceable agreement, raising doubts about his strategic depth in complex negotiations.
Domestic Deals (or Lack Thereof) in Washington
As President, Trump frequently touted himself as a master negotiator in the domestic political arena. However, here he encountered the realities of Washington deal-making, which depend heavily on compromise and coalition-building—not unilateral leverage.
Trump had some notable legislative successes, including:
The 2017 Tax Cuts and Jobs Act, a sweeping tax reform bill
The First Step Act (2018), a bipartisan criminal justice reform law
In the tax deal, Trump’s role was mostly cheerleading:
Congressional Republicans had long pushed for tax cuts
Trump supported the bill but did not personally craft its details
On the First Step Act, Jared Kushner again played a central role:
He lobbied conservative media and lawmakers behind the scenes
Pushed for sentencing reform, inspired in part by his father’s incarceration
Persuaded Trump to support the bill despite initial GOP resistance
Trump ultimately endorsed and signed the law, but the success is largely attributed to Kushner’s personal investment and cross-party outreach.
On the other hand, Trump’s highly publicized promise to “repeal and replace” Obamacare failed in 2017:
He could not secure enough votes in the Senate, even within his own party
The effort collapsed in part due to Trump’s limited policy knowledge and unwillingness to negotiate meaningful compromises
Other major domestic initiatives also stalled or failed, including:
Immigration compromises, such as exchanging border wall funding for DACA protections, broke down amid distrust and Trump’s shifting positions
Attempts to craft a grand infrastructure deal never materialized, despite public promises
In the 2018–2019 government shutdown over wall funding:
Trump’s tactic included walking out of meetings with Democratic leaders and declaring “no deal”
He eventually reopened the government without securing wall money, signaling limited leverage
These episodes reveal that Trump’s confrontational style, effective in business, did not easily translate to the complex negotiations of legislative governance.
Often, Trump deferred to Congressional Republicans or aides to work out details
When he did engage directly—usually through Twitter or public statements—his messaging often undercut ongoing talks
In several cases, Trump tentatively agreed to deals, only to back out after pushback from his base or advisors, revealing a lack of consistent strategic direction.
Assessment: Domestically, Trump’s deal-making fell short of the hype. Despite isolated successes, he secured fewer landmark bipartisan achievements than one might expect from someone who branded himself through The Art of the Deal. His presidency showed that negotiating legislation requires different skills—and often more patience—than closing business deals.
Overall, Trump’s deal history spans bold real estate ventures, savvy (and unsavvy) business negotiations, and unconventional political agreements.
Across this timeline, a clear pattern emerges: (1) Trump often sets the vision and public narrative for a “great deal,” (2) but frequently relies on teams of lawyers, executives, or diplomats to execute the complex negotiations.
When deals succeed, he is quick to claim full credit; when they falter, he labels them unfair or the fault of others.
Each major deal can be assessed on substance vs. marketing: some were truly beneficial (e.g. early property flips, Abraham Accords), others were more cosmetic or short-term (e.g. USMCA’s modest changes, the short-lived bump from the Phase One China deal), and some were arguably failures sold as successes (e.g. the heavily leveraged casinos, or the Afghanistan withdrawal deal’s consequences).
This duality makes it challenging to neatly categorize Trump as simply a brilliant deal-maker or not – the details matter in each case.
III.) “The Art of the Deal”: Trump’s Strategies vs. Real-World Practice
In his 1987 book The Art of the Deal, Trump (with ghostwriter Tony Schwartz) outlined his approach to negotiation and business success.
The book presents an 11-step formula or set of guiding principles for making successful deals.
Key themes from Trump’s advice include: “Think big,” “protect the downside and the upside will take care of itself,” “maximize your options,” “know your market,” “use your leverage,” “enhance your location,” “get the word out” (promote aggressively), “fight back,” “deliver the goods,” “contain the costs,” and “have fun.”
These maxims encapsulate Trump’s self-professed style – a mix of bold vision, shrewd risk management, constant self-promotion, and combative tactics to push through obstacles.
Comparing these strategies to Trump’s actual deal-making record reveals where he adhered to his playbook and where he deviated:
“Think Big” & Visionary Ambition: Trump has consistently thought big – from skyscrapers to seeking the presidency itself, he has never lacked ambition. His early deals like Trump Tower and the Taj Mahal casino show grand scale. As President, his summits with North Korea or the sweeping promise to redo global trade also reflect outsized goals. This matches his book’s counsel that aiming high gives an advantage in negotiations. However, thinking big can backfire without execution, and Trump sometimes overextended (e.g. the Taj Mahal’s budget and debt was enormous, ignoring the downside). In that case, he violated the rule of protecting the downside, as he did not sufficiently guard against the risk of low revenues. So while he fully embraced “think big,” the sober risk analysis part of his own formula was occasionally neglected.
“Protect the Downside” (Risk Management): One of Trump’s advices is to always hedge against worst-case scenarios. In practice, Trump’s record is mixed. On one hand, his use of bankruptcy laws can be seen as a form of downside protection – when projects failed, he shielded himself from personal ruin by restructuring debt (shifting losses to creditors). This shows strategic willingness to cut losses. On the other hand, those situations arose because he didn’t adequately protect the downside upfront: he over-leveraged his casino and hotel deals in the late ’80s, apparently assuming perpetual growth. As journalist John Tierney noted in 1991, Trump “appears to have ignored some of his own advice” from Art of the Deal when his empire ran into trouble, given the “well-publicized problems with his banks”. For example, Trump’s advice to contain costs was belied by his projects that ran on enormous debt and expenses. Only later, chastened by experience, did Trump become more risk-averse in investing his own money (preferring licensing deals where others put up the capital). So, early-career Trump did not consistently practice his preached caution, whereas later he became more prudent – indicating a learning curve in applying his principles.
“Use Your Leverage”: Trump excels at identifying and exploiting leverage. In negotiations, he often creates leverage by projecting a willingness to walk away or break the status quo. For instance, during NAFTA talks, Trump’s threat to cancel the agreement entirely created pressure that brought Mexico and Canada to make concessions. In real estate, he leveraged political connections (his father’s influence, or offering a stake to the city in future taxes) to obtain favorable terms like the Commodore Hotel tax abatement. In his book, Trump emphasizes always having alternatives and not appearing too eager – a tactic he used in 1985 when bidding on the Hilton casino in Atlantic City: Hilton had lost its license, so Trump swooped in with a below-market offer, effectively leveraging their distress. As President, his tariff threats were leverage to force trade partners to negotiate. However, Trump’s leverage tactics sometimes edged into brinkmanship. The government shutdown over wall funding was a case where he used the leverage of disrupting government services; ultimately this overreach hurt him politically and he had to relent. Another example is how he handled NATO allies – by hinting the U.S. might not fulfill defense commitments, he created leverage that arguably pushed allies to up their military spending, but also at the cost of alliance strain. Trump in practice did “use his leverage” aggressively, often to good effect, but occasionally he overplayed his hand, causing deals to fall through (as arguably happened in Hanoi with North Korea, when both sides walked away).
“Get the Word Out” (Public Relations): Perhaps no principle is more faithfully executed by Trump than the art of publicity. The Art of the Deal discusses how promoting your deal as a big win can help ensure it becomes one. Throughout his career, Trump has been a master of controlling the narrative. From inviting the press to witness minor construction milestones at the Wollman Rink, to staging signings of agreements with maximum pomp (e.g. the Abraham Accords signing mimicked historic peace treaty ceremonies), Trump has relentlessly “got the word out.” In real estate, he frequently inflated his accomplishments – using what he dubbed “truthful hyperbole,” an “innocent form of exaggeration – and a very effective form of promotion”. This promotional instinct often served him well by building the Trump brand, attracting investors or partners. However, it also meant sometimes the marketing gloss obscured middling results. For instance, calling USMCA “the best trade agreement ever” was a case of selling a deal harder than its fundamentals might merit. Trump adhered to the PR strategy in spades, enhancing his deals’ perceived value even if the real value was average. This can be double-edged: it boosts confidence and public support, but also opens him to criticism for overstatement when results are measured.
“Deliver the Goods”: Trump writes that after all the hype, you must deliver on your promises. His record here is variable. When he took on the Wollman Rink, he delivered results ahead of schedule and under budget, delighting New Yorkers. In his private business, he did complete major projects like Trump Tower and many buildings that are by all accounts high quality, fulfilling the core of what was promised to buyers or tenants. In contrast, some Trump ventures did not deliver as advertised – Trump University did not deliver a “year-long apprenticeship with Donald Trump” as its marketing implied, leading to those fraud claims. As President, “deliver the goods” could be seen in whether promised deals materialized: e.g., he promised to defeat ISIS (militarily, largely achieved by 2019), to renegotiate trade deals (achieved in part), but also promised a great healthcare replacement (which he did not deliver). There were cases of follow-through (Abraham Accords delivered peace agreements that exceeded expectations), and cases where the promise outran the delivery (North Korea denuclearization was never achieved despite the showy summits). Overall, Trump has shown an ability to deliver when the objective is concrete and within his control (build a building, sign a discrete agreement), but less success in delivering on more complex systemic promises (like sweeping policy deals or long-term arrangements).
“Fight Back”: Trump’s strategy includes never letting attacks or setbacks go unanswered. In negotiations, this translates to counter-punching and doubling down to gain respect or advantage. We see this in how Trump dealt with contractors or partners who crossed him – he has a long history of litigation and threats in business (hundreds of lawsuits). In Atlantic City, when Holiday Corp wanted out of Trump Plaza, Trump fought through legal maneuvers until he gained full control. Politically, when faced with criticism that his deals (like the North Korea talks) weren’t yielding much, he would lash out or shift tactics rather than concede failure. This tenacity can be a strength, deterring counterparties from trying to exploit him. However, “fight back” can also escalate conflicts unnecessarily. Trump’s pugnacious approach with adversaries sometimes made reaching a compromise harder (e.g. his personal attacks on Canadian PM Justin Trudeau during NAFTA talks created diplomatic spats, though the deal ultimately survived). In essence, Trump consistently applies “fight back” – he rarely shows concession publicly – which reinforces his tough negotiator image, but can burn bridges.
“Have Fun”: One often-overlooked Trump tenet is to enjoy the deal-making process. Trump has often expressed that he loves the game – the act of negotiating itself. In Art of the Deal he says he doesn’t do it for the money, but because “deals are my art form.” In reality, Trump does seem to thrive in the spotlight of deal-making, whether it’s haggling over a property price or hamming it up in a summit press conference. This enthusiasm can be an asset: it keeps him engaged and willing to take risks. It arguably helped him in 2016 portray himself as a happy warrior who would relish making “great deals” for America. The flip side is that treating everything like a show or game can lead to style over substance. Critics argue some of Trump’s negotiations (like the flashy meetings with Kim Jong-un) were done partly for show – for the “fun” and drama – without enough attention to technical follow-through. Nonetheless, enjoying negotiation likely gave Trump psychological endurance in drawn-out deals and an aura of confidence, which can intimidate opponents.
Trump’s real-world negotiations reflect many of the tactics from The Art of the Deal, but not always the underlying prudence or long-term focus that the book’s principles, at their best, would require.
He consistently “thinks big,” uses leverage and promotion masterfully, and fights tenaciously – these have been hallmarks of his career. Where he fell short was often in “protecting the downside” or “containing costs,” especially early on, and sometimes in truly “delivering the goods” beyond the initial deal fanfare.
It’s also critical to note that The Art of the Deal was as much a marketing vehicle as a guide – Tony Schwartz, the ghostwriter, later lamented that he might have painted too rosy a picture of Trump’s business acumen, calling his own book a regrettable act of myth-making.
Real life provided tests for each of Trump’s proclaimed strategies, with mixed outcomes. For every deal where Trump followed his rules to success (say, leveraging bankruptcy to strike a favorable deal or completing a project under budget), there’s a counterexample where hubris or overreach undermined the formula.
How Skilled of a Deal-Maker is Donald Trump? (Objective Analysis)
Evaluating Donald Trump’s overall effectiveness as a deal-maker requires separating the image from the evidence.
Trump undeniably built a powerful public persona as a master negotiator – through his best-selling book, reality TV fame, and constant self-promotion, he convinced millions that he could strike superior deals in any arena.
As President, this image sometimes became reality (e.g. diplomatic breakthroughs in the Middle East), but other times it collided with complexity (e.g. elusive agreements with North Korea or Congress).
Looking at decades of deals, a nuanced picture emerges.
Trump possesses certain real negotiation talents: He is bold, opportunistic, and unafraid to initiate deals others would shy away from (be it buying distressed assets or meeting rogue leaders). He leverages brinkmanship and unconventional tactics to unsettle counterparts and extract concessions – a strategy that has worked in some cases (NAFTA renegotiation, for example, did yield USMCA by using hardball threats). He’s also adept at reading public sentiment and using deals to score political points, an arguably different but important skill (turning even modest deals into perceived victories through salesmanship). Furthermore, Trump has shown a knack for recruiting capable negotiators (like Lighthizer or Kushner) and empowering them – a good leader knows when to delegate. In deals such as the Abraham Accords, this team approach paid off. These strengths suggest that Trump is not merely a charlatan; he has genuine instincts for leverage and showmanship that are valuable in negotiations.
However, Trump’s deal-making record is marred by inconsistency & overstatement: Many Trump deals have been less advantageous than advertised. In business, several ventures went bust or required rescue, indicating either flawed deal setup or poor execution (six corporate bankruptcies testify to that). He often claimed profit even when others bore losses – for instance, creditors and contractors often took haircuts in his restructurings while Trump escaped to fight another day. Critics argue this reflects skill in self-preservation, not necessarily in creating mutually beneficial deals. As President, some agreements were largely rebranding of existing frameworks (USMCA vs NAFTA) or short-term fixes. Trump also failed to close some big deals he pursued – no denuclearization deal with North Korea, no “better Iran deal” after abandoning the previous one, no grand infrastructure bill despite “Infrastructure Week” becoming a running joke. When facing a negotiating scenario that required compromise or sustained attention to detail, Trump showed impatience. For example, during COVID relief negotiations in 2020, he was often on the sidelines while Congress and his Treasury Secretary negotiated; at one point he abruptly ended talks via tweet, then reversed course – a sign of erratic strategy. Such cases fuel the argument that Trump is better at talking up deals than at painstakingly crafting them.
Staff Reliance vs. Personal Prowess: It is evident that Trump’s most concrete successes involved significant roles played by advisers or partners. In real estate, his father’s backing and experienced lawyers were key; in the White House, officials like Lighthizer, Kushner, and others did much of the heavy lifting. Trump himself tended to focus on the high-level vision and media narrative. This is not unusual for a CEO or President – delegation is necessary – but it raises the question: Was Trump the architect of his deals or mainly the marketer? The truth seems to be a bit of both. He often set the agenda (e.g. demanding a new trade deal, insisting on a Middle East deal) and created the conditions (sometimes by escalation) to force negotiations, which is a form of strategic leadership. Yet, when it came to the detailed trade-offs, he was inclined to accept what his team negotiated and declare victory rather than personally micromanage terms. For instance, he likely did not delve into the fine print of intellectual property rules in the China deal or the labor enforcement mechanisms in USMCA – he left those to experts. One could say Trump leveraged staff expertise while branding himself as the indispensable deal-maker, which is a skill in its own right (one of marketing and leadership, if not technical negotiation). But it also means his deal-making reputation is partly a one-man show built on a cast of many.
Image vs. Reality – The Overstatement Factor: There is ample evidence that Trump overstates his successes. As noted, he’s called modest revisions “historic” and spun setbacks as wins. This tendency makes it challenging to assess his skill objectively because perception has been managed so carefully by Trump himself. It’s telling that Tony Schwartz, who helped craft Trump’s myth in Art of the Deal, later suggested the book should be classified as fiction. That said, even critics concede Trump has an uncanny ability to sell a narrative. In negotiations, believing you have won can be as important as actual gains – and Trump ensures his side of the story always sounds like a win. This can boost morale and momentum for his projects, but when judged by cold facts, some deals simply don’t measure up to his claims (for example, manufacturing jobs didn’t flood back as a result of USMCA, contrary to his rhetoric). Therefore, while Trump is highly skilled at the theatre of deal-making, the substance of his deals ranges from strong to weak.
Considering all of the above, an overall assessment must acknowledge both Trump’s genuine deal-making abilities and his notable failings or exaggerations.
Is he a “genuinely skilled negotiator”?
Yes, in certain contexts – he has pulled off complex real estate turnarounds and has shown nerve and creativity in negotiations.
But he is also someone who leans heavily on others’ expertise and often claims full credit, and who has had significant missteps when he ventured outside his areas of core competence or when bluff and bluster met immovable reality.
AI (o1-pro) analysis of Donald Trump’s dealmaking ability:
Taking a balanced view, I would assess that Trump’s reputation as a deal-maker is about 40% earned skill and 60% strategic self-promotion.
In confidence terms, I am roughly 40% confident that Trump is a truly skilled negotiator in the conventional sense – meaning that in four out of ten cases he will personally negotiate a notably good outcome.
Why not higher? Because the record shows many of his “wins” required either bailout, compromise, or weren’t as big as advertised, indicating his personal negotiation technique doesn’t consistently outperform.
The remaining 60% reflects confidence that Trump’s deal-making persona is largely a product of leveraging others and spinning outcomes to appear successful. He is extremely adept at creating the impression of a great deal-maker, which in politics and business can sometimes matter more than the deal itself.
But when we strip away the branding, we see a deal-maker with some skill, some flaws, and a heavy reliance on the assistance and validation of others.
Donald Trump is neither the infallible deal-making genius that his fans imagine nor simply an incompetent braggart that critics portray.
He has demonstrated real negotiating prowess in certain deals (especially where bold vision and brinkmanship yield advantage) and has achieved some indisputable successes.
At the same time, his track record shows patterns of overreach, delegation to skilled deputies, and exaggeration of outcomes, which suggest his greatest talent often lies in marketing the deal rather than masterminding every element of it.
This evaluation, grounded in the facts of Trump’s career, supports a nuanced view: Trump is a highly shrewd but somewhat unorthodox deal-maker, one whose skill is intermittently effective and intertwined with a persona that sometimes outpaces the results.
Confidence level: Approximately 40% that Trump’s deal-making is as proficient as he claims, with 60% confidence that his successes are partly attributable to savvy branding and support from others.