Who is Witkoff? Dealmaker or Diplomatic Dice-Roller?
By: Asal Taheri
In the shadows of a 3 a.m. deli run with a young Donald Trump, Steven Witkoff, a Bronx-born real estate titan, began a journey that would defy expectation. With a $2 billion empire built on Manhattan’s skyline, he was an unlikely candidate to mediate peace in Gaza, negotiate with Russia’s Kremlin, or tackle Iran’s nuclear ambitions. Yet, Witkoff is doing precisely that, driven by a relentless focus on outcomes. “I don’t play for applauses– I play for results,” he told a close associate, a principle that has guided him from Manhattan boardrooms to the heart of international diplomacy.
Can this property tycoon navigate the treacherous waters of global crises, or will he falter under Trump’s unpredictability and a divided administration? Witkoff faces formidable hurdles: Trump’s sudden policy reversals erode his credibility abroad, while internal rivalries among clashing administration factions threaten to derail his initiatives. His lack of diplomatic experience invites skepticism as he juggles volatile regions and wary allies. The stakes are monumental, and the outcome remains uncertain.
Early Life and Loss
Steven Charles Witkoff was born on March 15, 1957, in the Bronx, New York, into a Jewish family shaped by determination and hard work. His father, Martin, ran a ladies’ coat manufacturing business in the city’s garment district, while his mother, Lois, fostered a stable home environment. The family later moved to Baldwin Harbor and then Old Westbury, Long Island, where Witkoff absorbed the tenacity of his grandparents, immigrants who had fled the Russian Empire for opportunity in America.
Zach Witkoff, Steve Witkoff’s son at the 2024 Republican National Convention
Witkoff married Lauren Rappoport in 1987, and together they raised three sons: Zach, Alex, and Andrew. Zach Witkoff serves as Executive Vice President of Development at the Witkoff Group and is a co-founder of World Liberty Financial, a cryptocurrency venture. Alex Witkoff is co-CEO of the Witkoff Group, steering major projects like the Shell Bay Residences in Miami. The family faced profound tragedy in 2011 when Andrew died of an opioid overdose at age 22, a loss that reshaped Witkoff’s perspective. This tragedy fueled his public advocacy, culminating in a compelling address at the 2018 White House Opioid Summit, where he declared, “This crisis demands action, and it starts with us.” In recent years, he relocated to Florida, settling near Donald Trump’s Mar-a-Lago estate, a decision that reflected both personal affinity and strategic alignment. Notably, Witkoff maintains a private collection of vintage New York City maps, a subtle tribute to his roots and a reminder of the urban landscape that shaped his early ambitions.
Academic Roots
Witkoff’s education was less about prestige than purpose. He began at Union College in Schenectady, New York, but found his footing at Hofstra University, earning a Bachelor of Arts in Political Science in 1980. “Power is a system—learn it, and you’re ahead,” he noted in a 2019 Hofstra alumni interview, revealing an early knack for strategic thinking. Hofstra Law School followed, where he secured a Juris Doctor in 1983, drawn not to courtroom drama but to the legal frameworks of real estate.
As a law student, he interned with a Manhattan firm handling property disputes, gaining an insider’s view of zoning and contracts that sharpened his edge. This practical focus helped him decode complex systems, a skill later evident in his diplomatic efforts. His time at Hofstra wasn’t just academic—it was where he honed a relentless curiosity, often staying late to debate policy with classmates, a habit that built his confidence in high-stakes negotiations.
Real Estate Triumphs
Steve Witkoff’s career ignited at Dreyer and Traub, a New York real estate law firm, where he worked with an up-and-coming Donald Trump. “He saw the board before the game started,” Witkoff said of Trump in a 2020 Financial Times profile, recalling a 1986 deli run for a ham and Swiss sandwich that cemented their alliance. After a stint at Rosenman & Colin until 1986, Witkoff craved ownership. In 1985, he co-founded Stellar Management with Laurence Gluck, a venture named for their initials, acquiring 85 apartment buildings–over 3,000 units– in undervalued areas like Washington Heights and the Northwest Bronx.
By 1995, Stellar targeted Manhattan’s office market, capitalizing on a downturn to buy low. In 1997, Witkoff launched the Witkoff Group, a family-driven firm that secured iconic assets: the Daily News Building, Woolworth Building’s upper floors, 33 Maiden Lane, and the Park Lane Hotel. A $650 million Park Lane deal in 2013 with Jho Low and the Abu Dhabi Investment Authority faltered amid the 1MDB scandal, leading Witkoff to sell his stake to Qatar Holding in 2023. His Middle East connections, including a May 2024 Qatar Economic Forum address, strengthened his global profile but drew scrutiny when he pivoted to diplomacy. Forbes estimated his net worth at $2 billion in 2025, ranking him 1,763rd worldwide. In 2021, he quietly extended a lease for a struggling Brooklyn community center at no profit, a rare move that reflected his blend of pragmatism and compassion.
From Law to Tycoon: Building an Empire
In 1985, he partnered with Laurence Gluck to form Stellar Management, pooling personal savings and securing bank loans to buy distressed properties in New York’s outer boroughs. Their strategy—targeting undervalued assets during a market slump—yielded high returns as property values rebounded.Witkoff’s shift from lawyer to real estate magnate was sparked by mentorship and market savvy. At Dreyer and Traub, he absorbed dealmaking from senior partners and Trump, whose bold vision inspired him to leave legal practice. “Law was a tool, but real estate was the game,” he told The Wall Street Journal in 1998.
The Woolworth Building, acquired by Witkoff in 1998To fund his empire, Witkoff leveraged partnerships and debt. By 1997, founding the Witkoff Group, he attracted institutional investors like the Abu Dhabi Investment Authority and used low-interest loans to acquire trophy properties. A 1995 office market crash allowed him to buy Manhattan buildings at steep discounts, flipping them for millions. His $130 million purchase of the Woolworth Building’s upper floors in 1998, funded partly by a $90 million loan, showcased his knack for high-stakes bets. Despite early financial strain—1998 reports noted his heavy leverage—he mitigated risks through joint ventures, amassing a portfolio of over 70 properties by 2025. His wealth grew through strategic sales, like the 2023 Park Lane stake, and developments like 20 Times Square, cementing his tycoon status.
A Bond Forged in Time: Witkoff and Trump’s Friendship
Steven Witkoff’s relationship with Donald Trump spans nearly four decades, rooted in a shared New York real estate hustle and deepened by personal loyalty. Their friendship began in the 1980s at Dreyer and Traub, where Witkoff, then a young lawyer, handled deals for Trump. A chance 1986 deli encounter—Witkoff buying Trump a ham and Swiss sandwich when Trump had no cash—became a touchstone, with Trump recalling the gesture years later. They bonded over golf, often playing at Trump’s West Palm Beach course, where Witkoff described Trump as “a fierce competitor who slows down on the fairway.” On September 15, 2024, Witkoff was golfing with Trump when a gunman, Ryan Routh, attempted an assassination, hiding in bushes with a rifle. Witkoff later told NBC News he heard “pops” and saw Secret Service agents shield Trump in seconds, praising their response. “He checked on everyone else first,” Witkoff said of Trump’s calm under fire.
Their connection goes beyond public moments. Witkoff hosted Trump at his son’s, Zach, 2022 Mar-a-Lago wedding, where Trump stayed late, dancing with guests. In 2011, after Witkoff’s son Andrew’s death, Trump called daily, offering quiet support—a gesture Witkoff shared at the 2024 RNC, saying, “That’s who he is off-camera.” Less known is their shared love of architecture; Witkoff once gifted Trump a 1920s blueprint of Manhattan’s Flatiron Building, a nod to their mutual obsession with iconic structures. Witkoff’s grandson, born in 2024, was named Don James Witkoff, a subtle tribute to his friend. This deep trust has shaped Witkoff’s role as Trump’s confidant and envoy, blending personal allegiance with strategic alignment.
Political Strategy: A Power Broker’s Quiet Influence
Witkoff’s political ascent was rooted in his decades-long ties to Trump, evolving from personal loyalty to strategic influence. A Jewish Republican, he prioritized outcomes over ideology, contributing $2 million to Trump’s 2020 campaign and sustaining support for 2024. His role extended beyond funding: he introduced Trump to key Jewish donors and mediated a critical reconciliation with Georgia Governor Brian Kemp, bolstering Republican cohesion. “The goal is alignment, not applause,” he remarked at a 2024 GOP gathering. Witkoff’s pragmatic streak showed when he backed Ron DeSantis in the 2024 primaries, hedging his bets to maintain influence.
In 2023, he orchestrated a discreet Florida meeting to sway GOP donors toward Trump, a move that shifted campaign momentum without fanfare. His political strategy hinges on building trust quietly, leveraging relationships to navigate divisive landscapes, a tactic that has made him a linchpin in Trump’s orbit. His July 2024 Republican National Convention speech was a call for unity behind Trump, delivered with understated conviction. Attending Benjamin Netanyahu’s congressional address that month, he noted privately, “Hostages aren’t abstract—they’re why we push.” Witkoff advocates for U.S.-Russia economic engagement to counter China, supports higher NATO ally contributions, and favors a streamlined U.S. defense budget.
Diplomacy Under Fire: Navigating Global Crises
On November 12, 2024, trump appointed Witkoff as U.S. Special Envoy to the Middle East, a choice that stunned observers, given his lack of diplomatic credentials. “Steven Witkoff will drive peace,” Trump stated, betting on his ally’s negotiation prowess. Witkoff also co-chaired Trump’s Presidential Inaugural Committee with Kelly Loeffler, underscoring his trusted status. Thrust into the Israel-Hamas conflict, Russia-Ukraine war, and Iran nuclear talks, Witkoff has approached each with a dealmaker’s focus, though his methods have sparked debate. His foreign policy reflects a belief in economic incentives and pragmatic concessions, often aligning with Trump’s push for swift resolutions, but critics argue his inexperience risks oversimplifying complex crises.
Trump’s trust in Witkoff stems from a 40-year friendship and Witkoff’s dealmaking grit. “Steve gets it done,” Trump told aides, per Axios, citing his Gaza ceasefire as proof. Witkoff pitched himself for the Middle East role, telling Trump, “Let’s try someone who thinks outside the box,” per Senator Lindsey Graham on NBC News. Seeing diplomacy as an extension of negotiation, Witkoff told Fox News, “It’s about finding the win for all sides.” Trump expanded his portfolio to Ukraine and Iran after the Gaza success, believing Witkoff’s loyalty and pragmatism could succeed where career diplomats failed. “When someone believes in you, you step up,” Witkoff told a confidant, per Politico, driven by duty and personal ties to Trump, who supported him after his son’s 2011 death. Yet, his lack of formal training and Trump’s reversals, like disavowing Witkoff’s Ukraine plan, raise questions about whether his appointment is strategic or a gamble on loyalty. Critics, including CNN’s veteran diplomats, warn he’s “outmatched” by counterparts like Russia’s Sergey Lavrov, testing his ability to navigate global flashpoints.
Gaza Ceasefire Efforts: A Breakthrough and Setback
Witkoff’s first major task was the Israel-Hamas conflict. In January 2025, he traveled to Israel, pressing Benjamin Netanyahu for a ceasefire and hostage exchange, meeting during the Sabbath to underscore urgency. “Lives don’t wait,” he told aides. On January 29, he became the first U.S. official to visit Gaza since the war’s 2023 escalation, overseeing the release of 25 living hostages, including American Edan Alexander, and eight remains—a six-week truce hailed as a win.
Collaborating with Biden’s envoy Brett McGurk and Qatar’s Sheikh Mohammed bin Abdulrahman Al Thani, Witkoff’s pressure on Netanyahu broke months of stalemate. The deal collapsed by March 18, 2025, with Witkoff blaming Hamas: “Their refusal to demilitarize sank it.” He remains focused on American hostages and a longer-term truce, though progress has slowed. His visits to Saudi Arabia and Qatar in February 2025 aimed to rally Arab support for a new framework, but regional skepticism persists.
Russia-Ukraine Negotiations: A Controversial Mediator
Witkoff’s portfolio expanded to Russia-Ukraine, with Trump designating him the primary envoy to Vladimir Putin. On February 11, 2025, he secured the release of U.S. citizen Marc Fogel in Moscow, swapping him for Russian Alexander Vinnik—a tangible success. His three-hour meeting with Putin laid the groundwork for ceasefire talks, though no deal materialized. Witkoff’s March 21, 2025, interview with Tucker Carlson, suggesting Russia retain four Ukrainian regions (Luhansk, Donetsk, Zaporizhzhia, Kherson), sparked outrage among Republicans like Marco Rubio and Keith Kellogg, who opposed territorial concessions. “Economic stability can reshape alliances,” Witkoff argued on Fox News, pushing U.S.-Russia trade to counter China. His April 2025 Moscow visit, including a dinner with Putin’s envoy Kirill Dmitriev, aimed to explore a “five-territory” deal, but Ukraine’s rejection of ceding land stalled progress. Critics, including posts on X, call his stance too Moscow-friendly, while supporters praise his boldness.
Iran Nuclear Talks: A High-Stakes Gamble
On April 12, 2025, Witkoff led nuclear talks with Iran in Oman, engaging Foreign Minister Abbas Araghchi in mostly indirect negotiations, with a brief, direct exchange—the first U.S.-Iran contact since Trump’s second term. Facing a 60-day deadline to avert conflict, he called the talks “constructive,” targeting a deal stricter than the 2015 JCPOA. “Iran’s advances demand ironclad terms,” he told NBC News, stressing verification. Further talks were set for April 19, 2025. Witkoff’s team, including Morgan Ortagus, explored prisoner swaps and sanctions relief, but Iran’s weakened position post-Israeli strikes complicated dynamics. Some in Trump’s circle, like Mike Waltz, favor military action, while Witkoff aligns with Trump’s diplomatic push. His April 2, 2025, offer to meet Iranian officials in Tehran was rebuffed by Supreme Leader Ali Khamenei, highlighting the talks’ fragility.
Additional Diplomatic Engagements
U.S. Middle East envoy Steve Witkoff, far left, attends a meeting with dignitaries, including U.S. Secretary of State Marco Rubio, Saudi Foreign Minister Prince Faisal bin Farhan Al Saud and Russian Foreign Minister Sergei Lavrov in Riyadh, Saudi Arabia
Beyond these flashpoints, Witkoff has taken on broader roles. In February 2025, he joined U.S.-Russia talks in Riyadh with Marco Rubio and Mike Waltz, discussing Ukraine but also exploring trade frameworks to reduce China’s influence. His March 2025 meetings in Saudi Arabia with Arab leaders focused on expanding the Abraham Accords, though no formal agreements emerged. Witkoff’s team has also engaged Lebanon, with Deputy Morgan Ortagus leading talks amid Israel-Hezbollah tensions, aiming to stabilize the border. In April 2025, he met European diplomats in Brussels to address NATO concerns over his Ukraine stance, reassuring allies of U.S. commitment while pushing for burden-sharing—a nod to Trump’s priorities. These efforts, while less publicized, show Witkoff juggling multiple crises, though some diplomats worry his stretched capacity risks diluting focus.
A Dealmaker’s Trial: Success or Stumble?
Steven Witkoff’s swift rise as a diplomat has ignited polarized reactions, reflecting his unconventional path. Supporters like Elon Musk, who praised his “unorthodox approach” on X, and allies like Jon Mechanic and David Friedman, who credit his Middle East instincts, see him as a bold outsider. Within the administration, Kelly Loeffler and Morgan Ortagus back his transactional style, viewing it as a break from diplomatic stagnation. Yet, he faces fierce opposition from Marco Rubio and Keith Kellogg, who criticize his Ukraine concessions as reckless, and Mike Waltz, who pushes for a harder line on Iran. A former State Department official, cited by Politico, argued he’s “playing catch-up against career diplomats,” pointing to the Gaza truce’s collapse as evidence of inexperience.
Witkoff’s challenges are magnified by Trump’s erratic leadership—public reversals, like his March 2025 disavowal of Witkoff’s Ukraine proposal after initial endorsement, sow confusion. The administration’s infighting, with Rubio’s hawkish camp clashing with Trump’s deal-driven loyalists, leaves Witkoff caught in the crossfire. His business ties to Qatar and Abu Dhabi, notably through the Park Lane deal, raise impartiality concerns, with posts on X questioning his ability to separate commerce from statecraft, though he counters, “Relationships are leverage, not liabilities.” His Gaza ceasefire, while a milestone, crumbled quickly, underscoring the limits of his approach in volatile regions. The Russia-Ukraine and Iran talks, still unresolved, test his resilience. Public sentiment on X swings wildly—some see him as a daring innovator, others a risky gambler.
Analyst Predictions: Can Witkoff Succeed?
Credible analysts offer mixed forecasts on Witkoff’s diplomatic tenure. Aaron David Miller, a former State Department negotiator, told Politico that Witkoff’s inexperience limits his effectiveness, estimating a 30% chance of reviving a lasting Gaza ceasefire due to Hamas’s intransigence and Netanyahu’s resistance. For Ukraine, Miller sees a 20% success rate, citing Witkoff’s “naive” concessions to Russia and Ukraine’s firm stance against territorial losses. On Iran, Fred Fleitz of the America First Policy Institute gives a 40% chance of a deal by mid-2025, noting Iran’s weakened position but warning of their “slow-walk” tactics. Fleitz suggests Witkoff could last until 2026 if Trump remains supportive, but Rubio’s influence might sideline him sooner.
Steven A. Cook of the Council on Foreign Relations argues Witkoff’s real estate lens oversimplifies conflicts, predicting a 25% success rate across all three regions unless he adapts to technical complexities. Conversely, Jason Greenblatt, a Trump-era envoy, told Newsweek that Witkoff’s outsider perspective could yield breakthroughs, projecting a 50% chance for Gaza progress if Arab states back him. Most analysts agree his tenure hinges on Trump’s patience—likely 12-18 months unless a major win emerges. As of now, Witkoff stands at a crossroads, his tenure a high-stakes test of whether a dealmaker’s playbook can resolve global crises or merely stir their complexities.
Can this property tycoon navigate the treacherous waters of global crises, or will he falter under Trump’s unpredictability and a divided administration? Witkoff faces formidable hurdles: Trump’s sudden policy reversals erode his credibility abroad, while internal rivalries among clashing administration factions threaten to derail his initiatives. His lack of diplomatic experience invites skepticism as he juggles volatile regions and wary allies. The stakes are monumental, and the outcome remains uncertain.
The Woolworth Building, acquired by Witkoff in 1998To fund his empire, Witkoff leveraged partnerships and debt. By 1997, founding the Witkoff Group, he attracted institutional investors like the Abu Dhabi Investment Authority and used low-interest loans to acquire trophy properties. A 1995 office market crash allowed him to buy Manhattan buildings at steep discounts, flipping them for millions. His $130 million purchase of the Woolworth Building’s upper floors in 1998, funded partly by a $90 million loan, showcased his knack for high-stakes bets. Despite early financial strain—1998 reports noted his heavy leverage—he mitigated risks through joint ventures, amassing a portfolio of over 70 properties by 2025. His wealth grew through strategic sales, like the 2023 Park Lane stake, and developments like 20 Times Square, cementing his tycoon status.
Steven Witkoff’s relationship with Donald Trump spans nearly four decades, rooted in a shared New York real estate hustle and deepened by personal loyalty. Their friendship began in the 1980s at Dreyer and Traub, where Witkoff, then a young lawyer, handled deals for Trump. A chance 1986 deli encounter—Witkoff buying Trump a ham and Swiss sandwich when Trump had no cash—became a touchstone, with Trump recalling the gesture years later. They bonded over golf, often playing at Trump’s West Palm Beach course, where Witkoff described Trump as “a fierce competitor who slows down on the fairway.” On September 15, 2024, Witkoff was golfing with Trump when a gunman, Ryan Routh, attempted an assassination, hiding in bushes with a rifle. Witkoff later told NBC News he heard “pops” and saw Secret Service agents shield Trump in seconds, praising their response. “He checked on everyone else first,” Witkoff said of Trump’s calm under fire.
Their connection goes beyond public moments. Witkoff hosted Trump at his son’s, Zach, 2022 Mar-a-Lago wedding, where Trump stayed late, dancing with guests. In 2011, after Witkoff’s son Andrew’s death, Trump called daily, offering quiet support—a gesture Witkoff shared at the 2024 RNC, saying, “That’s who he is off-camera.” Less known is their shared love of architecture; Witkoff once gifted Trump a 1920s blueprint of Manhattan’s Flatiron Building, a nod to their mutual obsession with iconic structures. Witkoff’s grandson, born in 2024, was named Don James Witkoff, a subtle tribute to his friend. This deep trust has shaped Witkoff’s role as Trump’s confidant and envoy, blending personal allegiance with strategic alignment.
Witkoff’s political ascent was rooted in his decades-long ties to Trump, evolving from personal loyalty to strategic influence. A Jewish Republican, he prioritized outcomes over ideology, contributing $2 million to Trump’s 2020 campaign and sustaining support for 2024. His role extended beyond funding: he introduced Trump to key Jewish donors and mediated a critical reconciliation with Georgia Governor Brian Kemp, bolstering Republican cohesion. “The goal is alignment, not applause,” he remarked at a 2024 GOP gathering. Witkoff’s pragmatic streak showed when he backed Ron DeSantis in the 2024 primaries, hedging his bets to maintain influence.
In 2023, he orchestrated a discreet Florida meeting to sway GOP donors toward Trump, a move that shifted campaign momentum without fanfare. His political strategy hinges on building trust quietly, leveraging relationships to navigate divisive landscapes, a tactic that has made him a linchpin in Trump’s orbit. His July 2024 Republican National Convention speech was a call for unity behind Trump, delivered with understated conviction. Attending Benjamin Netanyahu’s congressional address that month, he noted privately, “Hostages aren’t abstract—they’re why we push.” Witkoff advocates for U.S.-Russia economic engagement to counter China, supports higher NATO ally contributions, and favors a streamlined U.S. defense budget.
Trump’s trust in Witkoff stems from a 40-year friendship and Witkoff’s dealmaking grit. “Steve gets it done,” Trump told aides, per Axios, citing his Gaza ceasefire as proof. Witkoff pitched himself for the Middle East role, telling Trump, “Let’s try someone who thinks outside the box,” per Senator Lindsey Graham on NBC News. Seeing diplomacy as an extension of negotiation, Witkoff told Fox News, “It’s about finding the win for all sides.” Trump expanded his portfolio to Ukraine and Iran after the Gaza success, believing Witkoff’s loyalty and pragmatism could succeed where career diplomats failed. “When someone believes in you, you step up,” Witkoff told a confidant, per Politico, driven by duty and personal ties to Trump, who supported him after his son’s 2011 death. Yet, his lack of formal training and Trump’s reversals, like disavowing Witkoff’s Ukraine plan, raise questions about whether his appointment is strategic or a gamble on loyalty. Critics, including CNN’s veteran diplomats, warn he’s “outmatched” by counterparts like Russia’s Sergey Lavrov, testing his ability to navigate global flashpoints.
Witkoff’s first major task was the Israel-Hamas conflict. In January 2025, he traveled to Israel, pressing Benjamin Netanyahu for a ceasefire and hostage exchange, meeting during the Sabbath to underscore urgency. “Lives don’t wait,” he told aides. On January 29, he became the first U.S. official to visit Gaza since the war’s 2023 escalation, overseeing the release of 25 living hostages, including American Edan Alexander, and eight remains—a six-week truce hailed as a win.
Collaborating with Biden’s envoy Brett McGurk and Qatar’s Sheikh Mohammed bin Abdulrahman Al Thani, Witkoff’s pressure on Netanyahu broke months of stalemate. The deal collapsed by March 18, 2025, with Witkoff blaming Hamas: “Their refusal to demilitarize sank it.” He remains focused on American hostages and a longer-term truce, though progress has slowed. His visits to Saudi Arabia and Qatar in February 2025 aimed to rally Arab support for a new framework, but regional skepticism persists.
Witkoff’s portfolio expanded to Russia-Ukraine, with Trump designating him the primary envoy to Vladimir Putin. On February 11, 2025, he secured the release of U.S. citizen Marc Fogel in Moscow, swapping him for Russian Alexander Vinnik—a tangible success. His three-hour meeting with Putin laid the groundwork for ceasefire talks, though no deal materialized. Witkoff’s March 21, 2025, interview with Tucker Carlson, suggesting Russia retain four Ukrainian regions (Luhansk, Donetsk, Zaporizhzhia, Kherson), sparked outrage among Republicans like Marco Rubio and Keith Kellogg, who opposed territorial concessions. “Economic stability can reshape alliances,” Witkoff argued on Fox News, pushing U.S.-Russia trade to counter China. His April 2025 Moscow visit, including a dinner with Putin’s envoy Kirill Dmitriev, aimed to explore a “five-territory” deal, but Ukraine’s rejection of ceding land stalled progress. Critics, including posts on X, call his stance too Moscow-friendly, while supporters praise his boldness.
On April 12, 2025, Witkoff led nuclear talks with Iran in Oman, engaging Foreign Minister Abbas Araghchi in mostly indirect negotiations, with a brief, direct exchange—the first U.S.-Iran contact since Trump’s second term. Facing a 60-day deadline to avert conflict, he called the talks “constructive,” targeting a deal stricter than the 2015 JCPOA. “Iran’s advances demand ironclad terms,” he told NBC News, stressing verification. Further talks were set for April 19, 2025. Witkoff’s team, including Morgan Ortagus, explored prisoner swaps and sanctions relief, but Iran’s weakened position post-Israeli strikes complicated dynamics. Some in Trump’s circle, like Mike Waltz, favor military action, while Witkoff aligns with Trump’s diplomatic push. His April 2, 2025, offer to meet Iranian officials in Tehran was rebuffed by Supreme Leader Ali Khamenei, highlighting the talks’ fragility.
