Milton Glaser still loves New York, but these days, he said, it sometimes worries him. Mr. Glaser, 87, created one of the most potent designs of the last century: I ♥ NY, a rallying symbol for New York when the city and state were in crisis in 1977. On a recent afternoon, he puzzled over what design he would create for the New York of 2016.

This city, he said, is in a different crisis, brought on by its own success.

“That’s an enormous problem,” he said, seated in the canary-colored conference room of his design studio on East 32nd Street, where he has worked since 1965. Childish shrieks from the schoolyard next door rippled through the office. Scattered around the room were some of his recent designs, including bottles of Trump Vodka and a poster proclaiming, “To Vote Is to Exist.”

“You can’t have this much development, and the consequential eviction of hundreds of thousands of people who will have no place to live,” Mr. Glaser said. “There’s some fundamental misjudgment about the balance between ordinary people and people who make enormous amounts of money. The idea of apartments for $50 million. What? On what basis?”