Weiner has made moves before for Gracie Mansion, the mayor's residence. According to Stuart Loeser, former spokesman for Bloomberg, Weiner had planned to run in 2005 before dropping out when Bloomberg decided to run for a third term.
Though the pair have some history together, Bloomberg was conspicuously absent in criticizing Weiner after his Twitter scandal was exposed and other political leaders called for his resignation, Loeser said.
"I haven't had a conversation about him since it happened, but back then (Bloomberg) was the only one who wasn't piling on," Loeser said. "Throughout it, Anthony had said Mike was only one who went out of his way not to pile on."