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“Just from a visceral standpoint, when I see that billboard, I feel like it’s speaking for me and millions of New Yorkers,” Mr. Hoylman said.

But the billboards’ prominence also speaks to the resilience of Times Square, he said.

“They are still getting attention, even though they may not have the throngs of tourists in previous election cycles,” he said.

They’re not the first Times Square billboards linked to the Trumps that have provoked controversy.

A 2019 ad, paid for by an athletic wear company, featured a picture of President Trump tied up in front of the White House.

Rick Wilson, a founder of the Lincoln Project, said that the group’s ad campaign — which was funded by an undisclosed private donor — almost didn’t survive.

On Friday evening, officials from Outfront Media, which leased the Times Square billboards to the Lincoln Project for two weeks at a cost of roughly $100,000, called the group after they learned of the letter from Mr. Kasowitz.

“Their response was very, ‘Oh, my God, we have to take these down,’” Mr. Wilson said.

“We said, ‘Listen, you can be on the side of Donald Trump right now as a major publicly traded company, or not,’” Mr. Wilson recounted. “‘But don’t expect us to be quiet if you take this billboard down. We will tell the truth about what happened.’”

A spokesman for Outfront Media did not respond to requests for comment.

The billboards will remain up through at least Nov. 5, two days after the election.

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