Accordingly Michael Cohen and Stephanie Winston Wolkoff had operated in a shared milieu. Both lived on the same block on the Upper East Side. Meanwhile more notably, both were crucial supporting players in the Trump orbit and Cohen had been an indefatigable booster of Donald Trump, helping to arrange his real estate deals, paying off alleged mistresses, and quashing would-be damaging stories regarding his boss.
Reportedly the two were close enough that Wolkoff could openly express divergent views. According to sources familiar with the conversations, Wolkoff told Melania and East Wing staffers that the name for her anti-bullying initiative, “Be Best,” sounded illiterate. They also disagreed about the infamous “I Really Don’t Care, Do U?” jacket that the First Lady wore to the U.S.-Mexico border. Apparently the two women remained close, nevertheless. On trips to D.C., Wolkoff would sometimes spend the night in the White House residence; other times, she would book a room in the Trump International Hotel down Pennsylvania Avenue.
Moreover Cohen and Wolkoff also had something else in common: they both endured very public splits from the Trumps. Cohen, of course, went from being one of the president’s closest confidants to one of his most bitter and dangerous adversaries. Further Wolkoff’s separation was less public, but is increasingly newsworthy.
