Peter Chatzky, a wealthy tech executive, transformed the crowded race to flip a key New York congressional seat when he plowed $5 million of his personal fortune into his campaign this winter.
Almost overnight, the infusion made him a top contender for the Democratic nomination to take on Representative Mike Lawler, a Republican. And it helped Mr. Chatzky burnish his image as a businessman and progressive.
But as the Democrat’s profile has risen in the Hudson Valley district, so has scrutiny of his limited record — including a yearslong penchant for bawdy musings on Facebook that could undermine that image just as quickly.
In posts over the past decade, Mr. Chatzky, 65, speculated about how much he would have to pay Melania Trump, the first lady, to have sex with him. He joked about hosting a sex party for swingers and sleeping with a hypothetical intern. And he boasted — evidently facetiously — about people paying to watch him masturbate.
Mr. Chatzky wrote about Mrs. Trump on the night she addressed the Republican National Convention in 2016 and faced accusations of plagiarism.
“Oh come on. You know you’d still” have sex with her, he wrote, using a more vulgar term.
The post prompted a string of comments from male and female friends speculating about how much Mrs. Trump might charge for a “quickie.” Mr. Chatzky replied to one message: “$800 an hour. So about $80 then. I can afford that.”
Mr. Chatzky’s campaign declined to comment on the posts or the intention behind them. His campaign manager, Alyssa Verrelli, blamed his rivals, saying they were wasting time digging up old posts “to attack fellow Democrats.”
“Peter is focused on defeating Mike Lawler in November so that we can abolish ICE and make life more affordable,” she said.
All the posts are publicly available and remained online as of Wednesday afternoon. Selections have circulated among Democrats interested in the race, who drew a New York Times reporter’s attention to them.
The lewd comments could be a liability in the closely watched contest. Mr. Lawler is among the most vulnerable Republicans nationwide, and Democratic leaders have indicated they will have little tolerance for anything that could jeopardize their chances of winning the seat, which they see as a necessity for retaking a House majority.
“He may be attempting humor,” Suzanne Berger, the chairwoman of the Democratic Party in Westchester County, said of Mr. Chatzky. “But red lights should flash when objectifying women or girls in service of a joke.”
Mr. Chatzky’s most formidable opponents — Cait Conley, Beth Davidson and Effie Phillips-Staley — are women, and the contest has become increasingly negative as they vie for pre-eminence.
Mr. Chatzky built his fortune on a software company he founded in the 1980s. On financial disclosure forms, he has reported assets valued between $19 million and $59 million, though that does not include the value of his ownership interest in his business.
He entered the race for the 17th District last May, and put more than $5 million into his campaign in December. He has positioned himself to the left of most of his primary opponents, calling for the abolition of the Immigration and Customs Enforcement agency and praising Mayor Zohran Mamdani of New York City, a favorite target of Mr. Lawler.
Mr. Chatzky’s sexualized social media commentary stretches over about a decade and appears alongside affectionate posts about his wife, more anodyne jokes and political opinions. Some posts overlap with his time serving as the deputy mayor of Briarcliff Manor, an affluent village in Westchester County. (Earlier, he served as mayor.)
In February 2017, Mr. Chatzky posted about a Facebook friend request he had received from what appeared to be a fake account attempting a common scam: He shared screenshots of the requester’s profile, which showed a young woman who said she was looking for sex.
“Some of you may know her from PTA or Junior League,” he wrote, adding, “Anyway, long story short, key party at my house on Friday,” a reference to a type of sex party.
“Wasn’t she your intern when you were mayor, Peter?” a friend wrote in the comments.
“Not yet,” Mr. Chatzky replied.
That July, he posted a screenshot of a Google search for “enhancing breasts in photoshop.”
“I will be largely unreachable today,” he wrote.
He made jokes about sperm, masturbation and sexual arousal. In 2014, he bantered with friends about whether he was too old to have an intimate relationship with Mary-Kate and Ashley Olsen, then in their 20s.
Mr. Chatzky played along when friends, or even his wife, chastised him, too.
“Oh Peter!” someone wrote in response to one such post.
“Congrats,” he replied. “That’s the one millionth ‘Oh Peter!’ I’ve heard in my lifetime.”
Nicholas Fandos is a Times reporter covering New York politics and government.
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