Barring a very big surprise, Philip Levine, the super wealthy businessman and Miami Beach mayor, will formally announce his candidacy for the Democratic nomination for governor. He is little known across the state (He goes by Philip, by the way, not Phil), but also a savvy, well-connected political player with personal wealth and image — a take charge CEO type, rather than another typical politician — who immediately emerges as clearly the biggest threat to nominal front-runner Gwen Graham winning the nomination.

We've been writing for more than a year that Levine should be viewed as a formidable and unconventional gubernatorial contender. But a host of questions and potential vulnerabilities loom over his prospects for success. He has been a major Democratic donor for years, but his only elections have been in Miami Beach – not exactly a microcosm of Florida – and he spent $2 million to win 5,600 votes and the office in his first election.

The recent mailer shown above — from opponents of a ballot measure to halt booze sales on Ocean Drive at 2 a.m. — shows how even in his own backyard, Levine faces attacks as yet another wheeler-dealer politician.

What other attacks can Levine look forward to if and when his campaign for governor picks up steam? Some that come to mind:

***Pay to play. The flier shown here reflects the knock from his Miami Beach critics (and they are easy to find) that Levine's business and political interests have too often overlapped with his governing decisions. That includes the Ocean Drive issue, and even his best-known achievement of tackling rising sea water and Miami Beach flooding since he ownsconsiderable real estate that the city early on helped protect with pumps and raised sidewalks and streets.

He is sure to face questions and/or attacks about a controversial political committee he ultimately shut down amid widespread criticism. "The political action committee is called 'Relentless for Progress' and it's strong-arming city vendors, developers, large commercial property owners and other businesses into making sizable 'donations,' Michael Putney, WPLG Local 10's senior political reporter wrote in a 2015 Miami Herald column.

Relentless for Progress bought a full page ad in the Herald attack Putney, an experienced and widely respected journalist, as "sleazy" and unprofessional. Which brings us to another area Levine is likely to face criticism.

###His temperament. The real estate and cruise industry mogul has a Donald Trump-like penchant for feuding with reporters and assorted critics from businesses to social media critics. The mayor has blocked critics from following him on Twitter, prompting one radio host and Democratic activist to sue Miami Beach for refusing to release a list of people blocked by the mayor.

In Levine's first campaign for mayor, he filed formal complaints and a lawsuit against critics and periodically refused to talk to a Miami Herald reporter covering him. He has recorded himself berating a double parked FedEx driver and attacked AirBnb on Twitter, saying his city "doesn't want what your selling!!!"

###Miscellaneous. Levine is championing a minimum wage increase, and his city is suing the state for blocking it. But it's not hard to envision opponents attacking him for having made many millions in a industry, cruise lines, periodically accused of exploiting workers, evading U.S. taxes, and/or polluting.

If he wins the Democratic nomination, you can bank on Republicans hitting him as a tax and spender. Under Levine's watch,Miami Beach raised sewer rates, parking fines, and fees for parking and building permits.

None of this is meant to suggest Levine is a weak or doomed candidate. After months of campaigning, none of the other Democrats – Gwen Graham, Andrew Gillum, and Chris King – have shown themselves to be heavy favorites and one could make the case the Levine is best positioned to win at this point.

What is clear, however, is that for all his money, political and biographical assets and ability to spend millions of dollars (He has signalled a willingness to spend millions, but not tens of millions), Levine remains untested.

Welcome to the NFL, Mayor Levine.