When Steve Witkoff landed in Tel Aviv this month to negotiate hostage releases, Lauren Olaya stepped off the plane beside him. But the woman who spent 37 years building the Witkoff fortune watched from New York, her name still legally attached to an empire she helped create.
Lauren Rappoport’s story is one of quiet power. The Manhattan real estate attorney married Steve Witkoff in 1987 when both were grinding through property deals at competing law firms. She worked at Botein, Hays & Sklar. He was at Dreyer & Traub. Their marriage merged two legal minds into what became a $2 billion real estate operation.
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The Legal Foundation
Rappoport specialized in complex property transactions and commercial leases. While Steve became the public face of the Witkoff Group, she provided the legal architecture that made the deals work. Her name stayed off press releases, but her fingerprints were on every contract.
The firm acquired landmark properties across Manhattan. The Woolworth Building. The Daily News Building. Park Lane Hotel. More than 70 buildings total. Each deal required the kind of legal precision Rappoport brought from her years in corporate law.
Three Sons, Three Different Paths
The couple raised three boys in New York:
Andrew Witkoff died at 22 in 2011 from an OxyContin overdose at a California treatment facility. He had been feeding homeless people outside a church near their Park Avenue home. The family sued the One80 Center for wrongful death. Steve later spoke at the 2018 White House Opioid Summit, channeling grief into advocacy.
Alexander Witkoff now runs the family business as co-CEO. He manages luxury projects like The Brook in Brooklyn. Recently, The New York Times reported he was seeking billions from Middle Eastern sovereign wealth funds at the exact moment his father was negotiating ceasefires in those same countries. The timing raised questions nobody wanted to answer.
Zachary Witkoff co-founded World Liberty Financial, a cryptocurrency company with Trump family ties. He married at Mar-a-Lago in 2022. Trump danced until 4 a.m.
When the Marriage Ended
The separation happened quietly in 2024, shortly before Trump tapped Steve for Middle East envoy. No public statement. No court filings reported. After nearly four decades together, they simply stopped being married.
Steve moved to Miami Beach. He started dating Lauren Olaya, a former professional golfer who founded a women’s golf apparel line. She now travels with him on diplomatic missions, a reality that puts her on private jets to Moscow and Abu Dhabi while the original Lauren remains in New York.
The timing matters. Steve’s appointment came in November 2024. The separation appears to have happened around the same time. Whether one caused the other or they simply coincided remains unclear.
The Diplomatic Turn
Steve Witkoff had zero diplomatic experience when Trump named him Special Envoy to the Middle East. What he had was loyalty. He bought Trump a ham and cheese sandwich at 3 a.m. in 1986 when the future president forgot his wallet. Trump remembered for 38 years.
That loyalty landed Steve in the middle of Gaza ceasefire talks, then Ukraine negotiations, then Iran nuclear discussions. He told Middle Eastern officials about losing Andrew, connecting his personal tragedy to theirs. The tactic worked. A ceasefire deal came together in January 2025.
CNN reported that Steve works without a government salary and pays for his own travel. He logs more than 1,000 hours annually on Trump’s behalf, flying his private jet between conflict zones while his sons run the business he and Lauren built.
What She Left Behind
The Witkoff Group continues operating with Alexander at the helm. The business Lauren helped construct through decades of legal work now generates deals she may never see. Her sons carry the family name into cryptocurrency and international real estate while their father rewrites Middle East policy.
Steve keeps an office in the West Wing that once belonged to Ivanka Trump. He meets with Putin, Netanyahu, and Iranian negotiators. Media coverage rarely mentions the attorney who made the money that funded his independence, who raised the sons now running the operation, who buried a child and emerged on the other side.
The Price of Building Empires
Lauren Rappoport remains out of public view. No social media presence. No interviews. No statements through representatives. She built her career on discretion, and she’s maintaining it now.
Her professional legacy sits in Manhattan real estate titles and corporate structures that will outlast any marriage. Her personal legacy walks through the Witkoff Group offices and flies to Middle Eastern capitals. The family she raised with Steve continues the work they started, even as the family itself has fundamentally changed.
In an industry where everyone wants credit, Rappoport took a different path. She did the work, raised the children, survived the loss, and when the marriage ended, she let it end without turning it into a spectacle. That kind of strength doesn’t make headlines. But it builds empires that do.
