From Greenbacks to Gaza: A socialist candidate's sharp turn on wealth and war

Lindsey Boylan’s political journey reads like a switchblade folding back on itself. Once a Cuomo aide who accused her boss of harassment, she now stands beside Mayor Mamdani as a Democratic Socialist hoping to win a City Council seat in Greenwich Village. But two properties worth nearly ten million dollars, plus landscaping bills that could fund a small park, make her “socialist” credentials wobble like a drunk karaoke singer. Boylan lives in Bedford, New York with her husband, LeRoy Kim, a high-flying investment banker who rubs elbows with billionaires at a secretive Idaho conference nicknamed “Summer Camp for Billionaires. ” Their five-bedroom mansion costs thousands monthly just to keep the lawn looking like a golf course. Yet on the campaign trail, Boylan rails against inequality. Critics ask how she squares a seven-figure lifestyle with fighting for tenants who can’t afford groceries. One union leader put it plainly: “If that’s socialism, I’ll take the free market. ”Her views on Israel have performed an even sharper about-face. In 2019, she told Jewish Insider she had “unshakeable support” for Israel. Fast-forward to this year, and she brands Gaza a “genocide” while calling civilian deaths unacceptable. This new line fits neatly with Mamdani’s camp, but ignores her own past alliances: in 2020 she campaigned alongside a Brooklyn power broker who once promoted fraud and opposed gay marriage—hardly crowd-pleasers in a district proud of Stonewall’s legacy. Boylan has tried for office twice before and lost both times. Urban voters have grown tired of her stepping-stone runs. Now she seeks the seat vacated by Erik Bottcher, a gay city senator. Bottcher backs his former aide Carl Wilson, who is openly gay and widely favored by local Democratic groups. The Working Families Party, another far-left ally, also backs Boylan, even as her wealth gags critics and her policy pivots raise eyebrows. Her latest statement dodges questions about money and bombshells about Israel. Instead, she vows to champion LGBTQIA+ rights and affordable housing. Yet many in the district wonder if Boylan’s sudden socialist chic is more performance than policy. After all, speeches about queer youth are easier to give when you can retreat to a $6 million manor each night.