Things don’t usually go according to plan when a New York real estate mogul gets involved in global diplomacy. Steve Witkoff, a longtime friend of Donald Trump, is now the U.S.
Special Envoy to the Middle East, and he had a big part in the Gaza ceasefire deal. At 68 years old and with no formal diplomatic training, his switch from making deals on skyscrapers to ceasefires has sparked both strong support and sharp criticism.
Key Takeaways
- Witkoff has gone from working in real estate to one of the most difficult diplomatic jobs in the Trump administration.
- He helped come up with the “Witkoff Plan,” which calls for a 50-day ceasefire in Gaza with hostages freed and aid flowing.
- People are very upset about his appointment because of possible conflicts of interest and qualifications.
- Under Trump’s agenda, he is now working on diplomacy in not only Gaza but also Iran and Ukraine.
Who is Steve Witkoff?
Witkoff went to Hofstra University and then became a lawyer and real estate developer after growing up in the Bronx. In 1985, he helped start Stellar Management, and in 1997, he started the Witkoff Group, which is known for buildings like the Woolworth Building in Manhattan and the Shore Club in Miami. His close ties to Trump in the 1980s made him a key member of Trump’s inner circle.
Trump made him Special Envoy to the Middle East in 2025 and later Peace Missions Envoy.
The Deal to Stop Fighting in Gaza
Witkoff and Jared Kushner worked together in October 2025 to announce the “Witkoff Plan,” a U.S.-backed cease-fire in Gaza. Its main points are:
- Hamas freed 48 hostages, including 20 who are thought to be alive.
- Israeli Withdrawal: The IDF pulled back from areas in northern Gaza.
- Aid Surge: Humanitarian aid made it easy for people to get into Gaza.
- Prisoner Exchange: Israel agreed to let go of 2,000 Palestinian prisoners, 250 of whom were serving life sentences.
Witkoff went to Egypt from October 7 to 9 to get both sides to talk. Phase I began on October 11. Hostages were released and displaced Palestinians went back to Gaza.
He went to an IDF base with Adm. Brad Cooper from CENTCOM to make sure everything was in order.
He also spoke to crowds in Tel Aviv’s Hostages Square, where some people booed Prime Minister Netanyahu.
What Makes His Role So Controversial
People are going crazy on social media. This is very divisive, as shown by the fact that it was mentioned over 50,000 times in one week.
Supporters call him “the deal-maker of the century.” There have been more than 15,000 mentions of #TrumpNobel. People say that his efficiency and outsider status are good things about him.
Critics respond – People who don’t like him say he’s not fit for diplomacy. Critics are using hashtags like #WitkoffGenocide a lot. A New York Times article brought up possible conflicts of interest—his son Alex was said to have had ties to Middle Eastern investors in the deal’s negotiations.
The Guardian
His public speaking style also draws attention. At Hostages Square, he spoke emotionally about his late son Andrew (died of overdose in 2011), linking his grief to the families waiting for hostages. Some saw that as powerful, others as theatrics. His “sweater gaffe” at the Western Wall also became fodder for mockery.
What Lies Ahead
Witkoff’s remit now reaches beyond Gaza. He is tackling negotiations over Iran’s nuclear program and even Ukraine-Russia tensions under Trump’s “peace through strength” doctrine.
He continues to push new terms in Gaza. In May 2025, he proposed a 60-day ceasefire plan with staged hostage exchanges. Hamas responded with suggested amendments.
Witkoff has also faced resistance. He once withdrew U.S. teams from talks over Gaza when Hamas’s response seemed weak.
And he has visited aid sites in Gaza, including one run by a U.S.–Israel–backed foundation that the U.N. criticized as unsafe.
Will this ceasefire hold? Can Witkoff bridge the deep divides in the Middle East? His rise is proof that loyalty and ambition can thrust you into global spotlight—whether you are fully ready or not.
