Charlie Crist’s political career has become a cautionary tale about reinvention gone wrong.
The former Florida Governor keeps losing elections no matter which party label he wears.
And Charlie Crist hit Ken Welch with a nasty surprise that could upend one important 2026 race.
Crist confirms he’s considering eighth campaign in two decades
The Tampa Bay Times confirmed that Charlie Crist is eyeing a 2026 bid for St. Petersburg Mayor.¹
For weeks, political insiders whispered about whether the former Governor would challenge incumbent Mayor Ken Welch, and Crist finally acknowledged he’s "seriously considering" entering the race.²
Before making any final decision, Crist plans to consult with his family, including fiancée Chelsea Grimes.³
If Crist runs, it would mark his eighth bid for public office since the early 2000s.
His recent track record isn’t encouraging – Crist lost his 2022 gubernatorial race against Ron DeSantis by nearly 20 percentage points after resigning his Congressional seat to focus on the campaign.⁴
That crushing defeat came after previous losses for U.S. Senate in 2010 and Governor in 2014.⁵
Crist holds the rare distinction of losing statewide Florida elections as a Republican, an Independent, AND a Democrat.⁶
Political analysts have called him "a man with no convictions" who simply "went with whatever was popular at the moment."⁷
Welch suddenly facing Democratic civil war
The timing of Crist’s announcement creates maximum chaos for Welch.
Just one day before Crist confirmed his interest, St. Petersburg City Council member Brandi Gabbard – also a Democrat – announced she was running against Welch.⁸
The Tampa Bay Times reported Gabbard’s "commitment to run for Mayor is firm" despite previously endorsing Welch in his first mayoral campaign.⁹
Gabbard explained her challenge stems from what she described as a "clear difference in approach to governing."¹⁰
Both Gabbard and Crist supported Welch’s 2021 mayoral campaign.¹¹
Now they’re turning on him.
Welch won his 2021 election in a landslide, defeating Republican Robert Blackmon by more than 20 percentage points.¹²
As a Pinellas County Commissioner before that, Welch ran unopposed in 2008 and 2016.¹³
The closest he came to a competitive race was 2012, when he crushed challenger Maria Scruggs by 29 points.¹⁴
Scruggs has filed to run again in 2026, though her third-quarter fundraising reports showed minimal financial support.¹⁵
Crist brings massive name recognition but carries heavy baggage
Look, Crist would bring something to this race that neither Welch nor Gabbard can match – universal name recognition across Florida.
His decades-long political career gives him instant credibility with voters and the kind of fundraising muscle that could change everything overnight.
When Crist secured the Democrat nomination to challenge DeSantis in 2022, he raised $1 million in the first 24 hours.¹⁶
Compare that to Welch’s political committee having just over $200,000 on hand currently.¹⁷
But Crist’s party-switching history tells you everything about what drives his political decisions.
He started as a Republican in the Florida Senate in 1993, served as Republican Governor from 2007-2011, switched to Independent when losing to Marco Rubio in 2010, then became a Democrat in 2012.¹⁸
Critics point to a famous "hug" between Crist and President Obama in 2009 as evidence that he destroyed his Republican career through political opportunism.¹⁹
Even liberal commentators called his memoir about the party switch "a dishonest and boring memoir" by "a man with no convictions."²⁰
Democrats bleeding voters creates opening for chaos
The real problem for Welch isn’t just facing two Democratic challengers – it’s that St. Petersburg’s Democratic advantage is evaporating.
Biden captured over 97,000 St. Petersburg votes in 2020 while Trump took fewer than 59,000.²¹
By 2024, Harris managed only 85,000 votes compared to Trump’s 57,000-plus showing.²²
Democrats lost 12,000 votes between those two elections while Republican turnout stayed essentially unchanged.²³
And 2026 will mark the first time the St. Petersburg Mayor’s race occurs in an even-numbered year, meaning turnout will likely match these Presidential Election patterns rather than the lower turnout off-year races Welch is used to.²⁴
The math creates an opening for Republicans to potentially field a candidate who could exploit a three-way Democratic split.
No Republican has emerged yet, but the structural dynamics favor conservative voters showing up in higher numbers than previous mayoral cycles.²⁵
St. Petersburg may remain a liberal stronghold, but the Democratic erosion combined with Welch facing friendly fire from two former allies makes 2026 far more unpredictable than anyone expected.
The irony is thick – Crist spent decades climbing the political ladder by switching parties whenever convenient, and now his potential entry could hand Republicans their best shot at St. Petersburg City Hall in years.
¹ Janelle Irwin Taylor, "Whispered rumors are getting louder; Charlie Crist confirms he is mulling St. Pete mayoral bid," Florida Politics, October 15, 2025.
² Ibid.
³ Ibid.
⁴ Ballotpedia, "Charlie Crist," accessed October 16, 2025.
⁵ Ibid.
⁶ Kevin Derby, "Charlie Crist Has Lost Statewide as Republican, Democrat, Independent," Breitbart, November 8, 2022.
⁷ Isaac Chotiner, Review of "The Party’s Over" in The New Republic, cited in Wikipedia entry for Charlie Crist, accessed October 16, 2025.
⁸ Janelle Irwin Taylor, "Brandi Gabbard commits to challenge Ken Welch for Mayor," Florida Politics, October 14, 2025.
⁹ Ibid.
¹⁰ Janelle Irwin Taylor, "Whispered rumors are getting louder; Charlie Crist confirms he is mulling St. Pete mayoral bid," Florida Politics, October 15, 2025.
¹¹ THE ‘BURG VOTES, "Welch won by widest margin in history," November 3, 2021.
¹² Janelle Irwin Taylor, "Whispered rumors are getting louder," Florida Politics, October 15, 2025.
¹³ Ibid.
¹⁴ Janelle Irwin Taylor, "Brandi Gabbard commits to challenge Ken Welch," Florida Politics, October 14, 2025.
¹⁵ RealClearFlorida, "The Rise and Fall of Charlie Crist," November 7, 2022.
¹⁶ Janelle Irwin Taylor, "Brandi Gabbard commits to challenge Ken Welch," Florida Politics, October 14, 2025.
¹⁷ Wikipedia, "Charlie Crist," accessed October 16, 2025.
¹⁸ Ibid.
¹⁹ Ibid.
²⁰ Janelle Irwin Taylor, "Whispered rumors are getting louder," Florida Politics, October 15, 2025.
²¹ – ²⁴ Ibid.
