The dust may have barely settled from a brutal Presidential campaign season, but in Florida the focus has already turned to the 2014 Governor’s race. During their annual Jefferson-Jackson event in South Florida, the Democratic Party message was clear. They are determined to defeat Rick Scott and take back the Governor’s mansion for the first time in sixteen years.

While only one statewide Democrat, State Senator Nan Rich, has officially declared her candidacy, two other Florida powerhouses have been prominently discussed as possible candidates – former Florida CFO Alex Sink, who ran unsuccessfully against Gov. Rick Scott in 2010, and former Republican Governor Charlie Crist, who did not seek re-election as Governor in 2010 so that he could pursue a U.S. Senate run for the seat now held by Sen. Marco Rubio.

I sat down in an exclusive interview with each of these leaders of the Florida Democratic Party and discovered that there are clear differences in how the three of them see Florida politics and where they would take the Democratic Party. Here is an inside look at their perspectives and my take on what they would need to do to secure the backing of voters.

Nan Rich

Micro-bio: Spent twelve years in Tallahassee as a House Rep and then as a State Senator, ultimately becoming the Senate Minority Leader in 2010. Now a full-time Gubernatorial candidate.

Her Brand: Sen. Rich is a self-professed “policy person”. Supporters are right when they cite her knowledge of policy and Florida’s history. She answered questions with a comfortable knowledge of where Florida has been and the specific laws that she feels need to be changed. She proudly puts her flag in the Progressive/grassroots camp.

Her Defining Issues: Medicaid expansion, women’s issues such as reproductive rights, education

How She Describes Her Leadership Style: Collaborative

What She Loves Most About Florida: Floridian’s shared commitment to their Environment

Her Biggest Strength: Nan Rich proudly seizes the mantle as one of Florida’s Democratic leaders. She was quick to remind me that she has been fighting and working in Florida politics as a Progressive for years and that she is ready for the job as Governor. With Alex Sink not yet declaring her intentions and Charlie Crist being a newcomer to the Party, Rich’s certainty in direction has already won over some of the die-hards in the state.

Her Achilles Heel: Fundraising. It’s far too early to say that Sen. Rich is incapable of raising money…particularly when she’s the only player in the game at this point. However, Alex Sink has proven her fundraising prowess during her previous race and Charlie Crist is being largely credited with generating hundreds of thousands of the dollars the Party raised for the Jefferson-Jackson event. With Rick Scott being backed by the infamous tycoons Sheldon Adelson and Donald Trump, dollars are certainly going to matter and Rich will have to focus strongly on that effort.

The Elephant in the Room: Nan Rich was denied an opportunity to speak at the Jefferson-Jackson gala event, a perceived snub that was gleefully mocked by the Florida Republican Party, who jokingly offered to pay for a room so that she could deliver her speech. Rich addressed the topic first, eager to get her statement on record.

“Don’t let the Republicans fool you,” she stated. “This is just another trick to try and divide the Party. The same people that were cozying up to me in the media about not getting a speaking slot will be the first ones to circulate a nasty flyer about my support of women’s reproductive rights. No matter what happens, Democrats are going to be united in 2014.”

What She Needs to Do To Win: Without millions of dollars on hand, Nan Rich is going to need to learn to harness the media in every possible way. Social media is (relatively) inexpensive and can reach an important constituency she will need to win, though she may find difficulty in getting her message across to those voters that are not as engaged (sort of like when Big Bang Theory’s Penny is trying to understand her friends’ “science stuff”). Traditional media coverage (a.k.a. free press) will be essential, since it will be the strongest tool she has to battle what is sure to be an onslaught of Rick Scott commercials. While she is certain in her positions, Sen. Rich will have to learn to be sound-bite friendly and a bit of a camera hog without feeling like she is selling out the seriousness of her campaign.

Alex Sink

Micro-bio: Was elected the Florida Chief Financial Officer after a 26-year career at Bank of America. Ran for Governor in 2010. Currently a Senior Advisor for Hyde Park Capital and a Co-Founder of the Florida Next Foundation.

Her Brand: Though she is now working full-time in the private sector and on supporting her non-profit organization, Florida Next, Alex Sink is still a prominent guest – and often speaker – at a number of political events. For many Democrats, Sink is still the name that comes to mind when they are asked to name Florida’s leader of the Party. With her years of business and financial experience, she is described as smart and reasonable. She proudly embraces the idea that she is a Floridian first who loves the state and its people.

Her Defining Issues: Education and stopping the “brain drain”, creating jobs, the environment, particularly the impact of sea level rise

How She Describes Her Leadership Style: Collaborative

What She Loves Most About Florida: The diversity of its people and places

Her Biggest Strength: As a former Gubernatorial candidate, Sink has amassed a wealth of experience. Should she decide to run again, she is determined to not make the same mistakes twice. Additionally she tends to be approachable by both donors and the working class. Years of being a visible “listener” that anyone can talk to has enhanced her ability to passionately articulate issues in a way that is relatable.

Her Achilles Heel: She lost in 2010. Supporters are quick to defend Sink’s campaign, reminding people that losses during the era of the Tea Party were much worse in other states. Critics argue that too much focus was spent on fundraising and not enough attention was paid to the ground game or visibility. A second candidacy would have to put a swift end to the “Monday-morning quarterbacking” before it becomes too big of a distraction.

The Elephant in the Room: Party supporters are not yet convinced that Alex Sink wants to run for Governor a second time. If she does not come out with a “fire in her belly”, she cannot possibly persuade them to support her enthusiastically. While Sink has been visible in her community and around the State, she has been intentionally selective in her public statements and press appearances. It remains to be seen if Alex Sink wants to run another statewide campaign, or if she decides that she can better serve Florida in another way.

What She Needs to Do To Win: If Sink decides that it’s time for a Rick Scott rematch, her announcement and first few weeks will make or break her campaign. She will have to strike a fine balance between acknowledging that her first campaign could be improved upon without appearing apologetic. She will need to seize the label as the presumed candidate, without seeming like she is strictly looking for a personal payback. She will also have to brush aside her challengers within the Party without dividing it. In other words, for Alex Sink it will be all about the messaging and the optics.

Charlie Crist

Micro-bio: The 44th Governor of Florida, winning as a Republican in 2006, after serving as state Education Commissioner and then Attorney General. Currently a class action and mass torts attorney for the firm Morgan & Morgan.

His Brand: Gov. Crist made an impassioned speech at the 2012 Democratic National Convention that contained his “Reagan-esque” moment, literally stating that he did not leave his party…his party left him. Crist has positioned himself as the alternative to the polarizing extremes, seeking to forage the compromises and difficult policy decisions that are best for Florida regardless of Party affiliation.

His Defining Issues: Education, the middle class, the environment, particularly how the natural springs and rivers are under siege

How He Describes His Leadership Style: Cooperative

What He Loves Most About Florida: The kindness of its people

His Biggest Strength: Despite losing his Senate bid to Marco Rubio, Crist still bears a “rock-star” status in the state. He handles both national and local press adeptly, illustrating that he is comfortable in the spotlight – which would prove useful for a Party looking for that charismatic leader to ignite its base. Crist may not yet have stated his intentions regarding the Governor’s race, but he has already captured the attention of voters that many candidates are unable to reach.

His Achilles Heel: Though he has been in Florida politics for decades, Crist is essentially the new kid on the block as a Democrat. His staff, his advisors and even his information sources (which are invaluable in Florida politics) are all going to have to be re-built essentially from scratch. Crist’s exit from the Republican party was met with particular venom from key figures such as Jim Greer, the former GOP Chair, who Crist considered a close friend at one time. The scars from those wounds are still visible, particularly when Gov. Crist remarked thoughtfully about the “warmth and kindness” that Democrats have shown him so far.

If Crist declares his intention to seek a second term as Governor he will have a steep learning curve in building a successful statewide campaign operation, and his first difficult lesson will be learning who he can trust.

The Elephant in the Room: Voters still don’t feel as if they know who Crist really is or how he would govern. His DNC speech certainly articulated why he changed parties, but he’s going to have to work even harder to convince Progressives that he won’t betray their values if he were elected. At some point a deeper conversation will need to be had to gain full Party support, particularly in light of some of his previous legislation. For example, Gov. Crist signed a gay adoption ban into law, a decision he now says he regrets. It remains to be seen if people see Crist as a man who has successfully bucked Tea Party extremism, or as the proverbial man without a country.

What He Needs to Do to Win: At the Jefferson-Jackson event, Gov. Crist appropriately behaved as if he were a guest in someone else’s home. It was a night of Democrats and he respectfully yielded to the Party on decisions about where he should be and how he could help most. However, that period of respect and politeness will need to come to a swift end when/if he assumes the role as captain of the Democratic ship.

Voters will not show up for a Crist that runs a cautious, “Romney-type” campaign, where the focus is solely on his opponent, and where the candidate is too moderate to sell a big vision. Those that supported Crist the first time are looking for their “Fearless Floridian” – that Harrison Ford, “Get off my plane!” leader – that defied polls to restore felons’ voting rights and hopped in a chopper to get to the scene of the BP Oil Spill. For Crist, courage will have to rule the day if Democrats will rule the state with him as Governor.


Originally published Huffington Post: