Donald Trump is not one of New York City's "great developers, according to Alicia Glen, New York City deputy mayor for housing and development.
"I think he's been a brilliant marketer and he's been able to license his name quite effectively, but when you think about the great developers of New York City who have been operating here for generations, I wouldn't put him in that category," Glen said Monday on CNBC's "Squawk on the Street."
One reason why Glen doesn't put Trump in that category is because of his aggressive approach to finding tax subsidies for his developments. She said it was "extraordinary the degree to which he would just keep hammering home his entitlement to every single dime that was available."
Glen, who oversaw tax programs for housing development when Rudy Giuliani was New York's mayor, explained that normally developers engage the city in a conversation about what the public gains in exchange for those subsidies.
"Quite frankly, he wasn't interested in that conversation. He wanted every single dime and he was absolutely relentless in his pursuit," she said.
While some may see Trump's determination to get every tax break that he can as evidence of his negotiating prowess, Glen said that his strategy has long-term consequences. She explained that it's not always best to "fight to the death" on every deal "because at the end of the day, you're losing trust."
The Trump campaign told CNBC in response to Glen's remarks, "Mr. Trump is a New York City icon and one of the great developers of the world."
The Trump Organization did not immediately respond to CNBC's request for comment.