The Hope Florida scandal has entered a new and more dangerous stage for the Governor and his allies.

What began as questions over a quiet $10 million Medicaid settlement routed through a charity led by First Lady Casey DeSantis has now escalated into subpoenas and a grand jury in Tallahassee.

As first reported by Florida Politics, subpoenas are being issued to senior staff past and present in the Governor’s Office, including former acting Attorney General John Guard, longtime DeSantis aide Kate Strickland and James Holton, the former Chair of one of the nonprofits that received millions from Hope Florida. While the State Attorney’s Office has not disclosed who exactly is under investigation, the reach of the subpoenas makes plain the seriousness of the probe.

Prosecutors in the 2nd Judicial Circuit are reportedly convening a grand jury for the week of Oct. 13, a clear sign the matter is no longer confined to legislative hearings and political finger-pointing.

This is a saga that has dragged on for months, even courting criticism from fellow Republicans. The latest update guarantees the scandal will stretch deeper into the Fall, dragging more of DeSantis’ inner circle into the spotlight and keeping questions alive about his administration’s handling of public funds.

Even if no charges ultimately emerge, the spectacle of a grand jury investigating a charity tied to the First Lady ensures Hope Florida will continue to dominate headlines, complicating the Governor’s efforts to move past the controversy and all but eliminating any chance the First Lady pulls the trigger on a gubernatorial bid.

Now, it’s onto our weekly game of winners and losers.

Winners

Honorable mention: Ralph Massullo, Maria Zack. Both Massullo and Zack came out on top in Special Elections this week in their respective Republican Primaries.

Massullo dominated the Senate District 11 contest, capturing nearly 80% of the vote against Anthony Brice. Massullo’s win was widely expected. He’s a former member of the House who used his name recognition and a well-oiled ground operation to sweep all four counties in the district.

In Palm Beach County, Zack survived a much tighter GOP Primary in House District 90, edging Bill Reicherter by a roughly 53%-to-47% split — a victory measured by just a few hundred votes. The HD 90 seat opened after the death of Democratic Rep. Joe Casello this Summer.

Massullo is extremely well-positioned to win the December General Election in SD 11. He won The district is heavily Republican — Blaise Ingoglia, whose resignation triggered this Special Election, won his 2024 race by nearly 39 points.

Massullo’s Democratic opponent, Ash Marwah, faces a steep uphill climb. Barring an unusual wave or massive turnout shift, Massullo enters the contest a heavy favorite.

Zack’s chances are lower, especially given her polarizing nature given past support of conspiracy theories. Casello in 2024 beat his Republican challenger by about 12 points. But Palm Beach County has experienced a rightward shift in recent years.

Zack will face Democrat Rob Long and an independent, Karen Yeh. If the GOP is energized and Long fails to fully consolidate Democratic voters, Zack could pull off an upset. But the odds tilt toward a Democratic hold unless Zack over-performs.

Still, there’s plenty to celebrate this week as she advances out of a hard-fought Primary many expected Reicherter to win.

Almost (but not quite) the biggest winner: Miami Dade College. For the second straight week, Miami Dade College earns a spot in the “winner” column, this time thanks to a pivotal Cabinet decision that pushes the Donald Trump Presidential Library one step closer to reality in downtown Miami.

Last week, MDC’s Board of Trustees agreed to transfer a 2.63-acre parking lot south of the Freedom Tower to the state, making it available for the project. This week, the Florida Cabinet signed off on the move, formally approving MDC’s role as the host site.

The Cabinet vote, led by Gov. DeSantis and supported by CFO Ingoglia, Agriculture Commissioner Wilton Simpson and Attorney General James Uthmeier, clears the way for the land conveyance.

Critics continue to question whether giving up prime real estate intended for campus expansion was wise. Certainly, Trump is not without controversy, and there are plenty of people unhappy to see his legacy tied to MDC.

But from a pure power-politics standpoint, the college has cemented itself as a central player in a legacy project that will draw national attention for years to come. It’s a major milestone for a college that isn’t at the same level as some of Florida’s leading higher ed institutions. To gain relevance requires taking big swings, and that’s what MDC is trying to do here.

The biggest winner: Patrick Zalupski. Zalupski, founder and CEO of Dream Finders Homes, closed on the purchase this week of the Tampa Bay Rays, a move that can position him as the man who finally puts to rest years of speculation about whether the franchise would bolt the region.

The Rays, despite their reputation for low payrolls and sparse attendance, have been one of the most consistently competitive teams in baseball. What they’ve lacked is stability. For more than a decade, relocation talk hung over the club, frustrating fans and local officials alike.

Zalupski’s acquisition provides the clearest signal yet that the team’s future is in Tampa Bay. His commitment to keeping the Rays rooted in the region is a stabilizing force for fans and local government officials alike that have spent years wringing their hands over the Rays’ future.

The purchase allows Zalupski to grow his already significant influence in the state. He serves on the University of Florida’s Board of Trustees, where he plays a hand in the direction of the state’s flagship university. The Rays have also courted The Southern Group, one of Tallahassee’s most powerful lobbying shops, to represent the Rays in government matters.

By sealing the deal, Zalupski did more than add “pro sports owner” to his résumé — he delivered peace of mind to a fan base and a community that feared losing one of its major-league franchises.

Losers

Dishonorable mention: Floridians without representation. It seems Gov. DeSlacking is at it again.

Two districts in Florida could go unrepresented to start the 2026 Session as DeSantis again drags his feet on calling Special Elections.

In Hillsborough County, the Florida chapter of the American Civil Liberties Union (ACLU) has filed suit over the Governor’s failure to schedule an election for Senate District 14, vacated when former Sen. Jay Collins was tapped as Lieutenant Governor.

The lawsuit argues DeSantis is violating both the Florida Constitution and long-established precedent, noting that past Governors acted within days to ensure voters weren’t left without a voice. The ACLU points out that this is a recurring problem under DeSantis, who has often acted quickly when the vacancy suited him politically, while stalling in other instances.

In Palm Beach County, residents there — including Trump himself — may be stuck without representation in House District 87 after DeSantis appointed former Rep. Mike Caruso as County Clerk.

Caruso told colleagues this week he has gotten no word from the Governor’s Office about whether an election will be called, and the election calendar makes it unlikely one could be held before Session convenes Jan. 13.

“It is important that the seat does get filled because we’ve got so many issues in the county,” Caruso said. “We want District 87 represented in the Florida House.”

That’s notable, as Caruso is a DeSantis ally. Also notable: Caruso’s wife recently withdrew from the race after a Trump-aligned candidate, Jon Maples, appeared to be amassing momentum in the GOP Primary.

That’s no reason to delay a Special Election, and we sincerely hope that isn’t playing into the Governor’s calculus. Because no matter the reason, these delays are leaving thousands without an advocate in Tallahassee.

Almost (but not quite) the biggest loser: Richard Corcoran. Two years into the conservative remake of New College of Florida, the project touted by DeSantis as a showcase for his fight against “woke indoctrination” looks increasingly shaky.

Despite a surge in state funding, with New College now spending more than $130,000 per student — more than 10 times the average of other institutions in the State University System — the school’s key metrics are trending downward. Graduation and retention rates have slipped since the makeover, and New College has fallen nearly 60 spots in the U.S. News & World Report rankings, even as other Florida schools climb.

Corcoran, a former Republican House Speaker brought in to run the school, has tried to downplay the rankings slide by blaming unfair criteria.

But that defense has done little to blunt growing concern among faculty, alumni and even members of the Florida Board of Governors about whether the experiment is sustainable.

Adding to the turmoil, Corcoran recently acknowledged during a Board of Governors meeting that if New College can’t distinguish itself, it might as well shut down — a remark that many took as a telling slip about conversations already happening behind closed doors.

For an institution that was supposed to symbolize Florida’s higher ed “success story,” it’s a failure by many metrics so far.

The biggest loser: Congressional delegation. With the federal government grinding into shutdown, there’s plenty of blame to go around in Washington — and Florida’s congressional delegation doesn’t get a pass.

This isn’t about one or two lawmakers misplaying their hand or a single faction derailing negotiations. It’s about the system breaking down, and Florida lawmakers are part of that system.

The shutdown means Floridians have felt real effects in disrupted services and delayed projects that ripple into communities across the state.

All delegation members have chosen to serve in Washington, where the primary responsibility is to keep the government functioning. Instead, partisan gridlock and brinkmanship have again left Floridians footing the bill for dysfunction.

For decades, members of both parties from Florida have claimed credit when the federal government directs funding, projects or disaster aid home. Well, when a shutdown causes the opposite to happen, you’ve got to bear the brunt of those effects as well.

And even just politically, the shutdown has allowed each national party to pump out ads playing the blame game and targeting vulnerable incumbents.

That makes every member of Florida’s congressional delegation — from Panhandle conservatives to South Florida progressives — losers this week, not because they caused the shutdown single-handedly, but because they couldn’t stop it.