On December 31, 2013, for the first time since 2001, Michael Bloomberg will not be mayor of New York.

During his three terms thus far, Bloomberg has been an outspoken leader, enacting controversial, sometimes unpopular legislation even in the face of massive criticism.

Following in the footsteps of former mayor Rudolph Giuliani, Bloomberg has tried to make New York as safe and prosperous as it can be, toughening up on crime and courting businesses and startups. 

Among New York political circles, it's long been suspected that popular City Council Speaker Christine Quinn would be Bloomberg's successor as New York mayor. 

The Speaker is an ally of Bloomberg's and was among the contingent who supported a rule change that allowed him to run for a third term. 

Unofficially, Bloomberg was said to be angling for Quinn, strategically trotting her out during fundraisers and press conferences. 

“There’s no question in my mind that of all the candidates, he sees Chris Quinn as far better for the city of New York,” former Mayor Edward I. Koch told the New York Times in 2011. 

That could be changing, though. Bloomberg, according to sources the Times spoke to, is becoming anxious about the current crop of  2013 mayoral candidates. Instead, "Mayor Mike" would prefer a successor who can rival his political clout and effectively take over the unwieldy reins of his position. 

The New York Times reports that special someone could be retiring Secretary of State Hillary Clinton, who the paper says has been contacted by the mayor about a potential campaign.

Spokespeople for Quinn, Clinton, and Bloomberg declined to comment, but the Times confirmed with three different sources that the call took place a few months ago with Bloomberg telling Clinton that she'd be a perfect fit. The Secretary of State, for her part, told the mayor she was uninterested.

Sources close to the conversation called it casual but earnest. The two are close, dating back to Clinton's days as a New York senator, where the pair spoke frequently about state policies and finances.

In Clinton, Bloomberg would be able to literally handpick a successor, devoting his fortune and Super PAC funding to Clinton's campaign. The former senator and the mayor hold similar views on gun control issues, a topic the mayor is especially vocal about.

Above all, Bloomberg reportedly relishes Clinton's ability as an intermediary and an emissary, working with foreign groups to forge alliances and create solutions. Elsewhere, he admires her ability to manage a large government bureaucracy, a similar task, he feels, to what he did as an elected official with boardroom experience. Quinn has none of that business experience, which could possibly bother Bloomberg.

Bloomberg does see himself as a kingmaker, and experts have long felt that the only way Quinn wouldn't become mayor would be if a high-profile candidate piqued Bloomberg's interest.

“If in fact he did say that to Hillary Clinton, it’s only because he holds the position and therefore regards it as a step up from being president,” Robert Zimmerman, a Democratic National Committee member from New York and a longtime fund-raiser for the party told the Times.

At this point, a Clinton mayoral run is still a long shot. While she maintains a residence in Chappaqua, New York, she does not live in New York City, which is required for mayoral candidates. Further complicating matters are rumors that Clinton may be considering a second presidential campaign in 2016.