With less than four months remaining in his tenure at City Hall, and no indication that he has plans to ride off into the sunset anytime soon, the three-term mayor is facing a difficult prospect: He is a wealthy man with grand ambitions for shaping the nation’s priorities on issues ranging from guns to immigration, but has a questionable ability to do so…

While New Yorkers have a long history of rewarding strong leaders with outsized personalities, the rest of the country may be less enamored of such an aggressive style, one that seems rooted in an attitude of “I know what’s best for you.”

“Part of the problem with Bloomberg is that politically he’s had a difficult time speaking to the public on their level,” said Jeanne Zaino, a professor of campaign management and political communication at NYU. “There’s a way in which his money can be very helpful, but it has to be done artfully and in a way that understands the local culture and views of outsiders, and he doesn’t seem to have mastered that. There’s a ‘real person’ sense that seems to be missing.”…

“He had the potential to be much more influential as a voice of independents, pre-2008 financial meltdown,” said New York-based Democratic strategist Dan Gerstein, a self-described fan of the mayor. “And I think he missed his moment because now, anyone who comes from the financial elite and has such strong ties to Wall Street is going to be compromised in the eyes of many.”