The crowded 2016 presidential race could be adding another billionaire business owner.

Over the weekend, entrepreneur and former New York City mayor Michael Bloomberg said he's considering entering the contest as an independent. If he joins, he'd be going head-to-head with real estate mogul Donald Trump, also of New York. Like Trump, Bloomberg comes with a strong business background and entrepreneurial street cred, though his political career has often been contentious.

Bloomberg first won the mayor's race as a Republican in 2001, after switching his party affiliation from Democrat. But he subsequently changed again in 2007 to independent, and despite considerable opposition successfully overturned term limits in the city so he could serve a third term.

The 73-year-old Bloomberg, who mulled presidential runs in 2008 and 2012, is willing to spend up to $1 billion of his estimated $36 billion fortune on the race, according to the The New York Times, and has set a deadline of March for his decision.

One of the wealthiest men in the country today, Bloomberg in the 1980s had been laid off from his job as partner at investment bank Salomon Brothers when it merged with a commodities trading firm called Phibro. As severance, Bloomberg received $10 million, part of which he used to start the massively successful financial information services company now called Bloomberg LP.

Bloomberg also showed his business acumen at City Hall, where he turned New York's $6 billion deficit into a $4 billion surplus. He did so, however, by initially raising property taxes to 18.5 percent, which was a record at the time. (In 2004, he returned $250 million to residential home owners.)

During Bloomberg's tenure, he applied his technologist's skills to streamlining vast city bureaucracies--most notably in New York's education system, where he closed 160 failing schools and opened nearly 200 new charter schools. He also rezoned 40 percent of the city, pushing waterfront development that included more parks and playgrounds, as well as more high-rent buildings, including office towers and condominiums. Toward the end of his term, the mayor ushered through $120 million in tax breaks for the developers of Hudson Yards, a project on the far West side of Manhattan, and Willets Point in Queens.

Eyeing the race

Bloomberg returned to the helm of his eponymous company at the end of 2014. He reportedly is thinking about joining the race now--just days ahead of the February 1 Iowa caucuses--due to the fumbles of Hillary Clinton, as well as his concerns about the rise of Vermont senator Bernie Sanders. And he reportedly is upset about the incendiary tone set by Republican challengers Trump and Texas senator Ted Cruz.

"People are looking for someone to stand above the fray, and the question is, could [Bloomberg] pull that off?", says Bill Whalen, a research fellow at the Hoover Institution, a nonpartisan think tank.

Even after three terms as mayor of the nation's largest city, Bloomberg's politics are still somewhat difficult to pin down. On many social issues, he is left of center, favoring abortion rights, stronger gun control laws, and same-sex marriage. He has also been criticized for pushing what some critics call "nanny state" policies, such as his proposed ban on large sugary drinks, and banning trans fats in restaurants.

For those reasons, it's not clear he would win too many staunch Republican votes, political analysts say. Many Democrats also view him with a skeptical eye due to his numerous party switches. 

As an independent, he is likely to siphon more votes from the Democratic contestants than Republicans, political experts say. But he could also attract votes of some moderate Republicans.

"He should just run in the Democratic primary," says Stan Veuger, a resident scholar and economist at the American Enterprise Institute, a conservative think tank in Washington D.C.