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Plate I · The entrance of GEO Group’s headquarters on Technology Way in Boca Raton
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The Lead · Politics · Boca Raton
The Oct. 8 check to Donalds’ PAC came six days after GEO’s $950 million sale of a California ICE complex to Homeland Security. No record ties it to the sale, a state contract or vote.
On Oct. 8, Boca Raton’s GEO Group, which the News Service of Florida calls “the largest private detention contractor in the country,” wrote Friends of Byron Donalds PAC a $1 million check, state records show, six days after it sold its Adelanto ICE detention complex in California to Homeland Security for $950 million. Donalds is the Republican nominee for governor on the Nov. 3 ballot, and no record ties the check to the sale, a state contract or a vote (Division of Elections; WLRN; GEO Group 8-K). Your stake: your next governor will run the office that holds a $100 million
emergency contract with a GEO-linked staffing firm, paid about $32 million so far, payments, not profit (FACTS; WLRN).
Old Florida Money desk · Wed Oct 21 · Sources: Florida Division of Elections (contribution records and 2026 reporting calendar, read Oct. 20); Florida Accountability Contract Tracking System (contracts E6113 and E6123); SEC EDGAR (GEO Group Forms 8-K of Oct. 5 and Oct. 8); WLRN and Jacksonville Today (News Service of Florida); Florida Politics; KESQ; WUSF; Bisnow; GEO Group releases
Read the full story
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Plate II · Besides petitioner New Jersey, Florida was one of ten states off the Supreme Court brief
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Money Pulse
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James Uthmeier didn’t sign as 39 states and DC asked the Supreme Court to take on Kalshi
Besides petitioner New Jersey, Florida was one of ten states off the Oct. 7 brief on whether states can police sports bets on prediction markets, and his office declined to explain, Politico reported (amici brief; Supreme Court docket; Next Event Horizon; Politico via Sunburn). The state’s sports betting runs through the Seminole compact, under which Florida received $1.04 billion last budget year; Kalshi’s reply is due Nov. 9 (News Service of Florida; Supreme Court docket).
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Larry Page’s reported Coconut Grove estates changed hands by deeds dated days before California’s billionaire tax line
Miami-Dade records show four deeds dated Dec. 26 to 29, 2025, moving five waterfront parcels to two revocable trusts for $127.9 million, by our sum; Page’s name is on none, and The Wall Street Journal and Business Insider report he is the buyer (Miami-Dade Property Appraiser; Fortune; Business Insider). California’s Prop 40, on its Nov. 3 ballot, would tax billionaires living there on Jan. 1, 2026 at 5% once and leaves out real estate held directly or in a revocable trust (Prop 40 text).
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Nearly all of a 1964 South Beach condo’s 238 homes sold deed by deed; the Vacchi-backed tower planned there borrowed $507M
County records show 146 deeds moved 216 of Bay Garden Manor’s units to the developers at listed prices averaging about $442,000, by our arithmetic, and Tyko Capital, backed by Paul Singer’s Elliott, made the construction loan before a single new condo sold (Miami-Dade Property Appraiser; Commercial Observer; Bisnow; The Real Deal). Sales of the 106 new condos start in 2027 (REBusinessOnline).
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Orlando’s Dr. Phillips Center won $350M of hotel tax, 6-1, two weeks before voters reshape the board that voted it
Orange commissioners cut the mayor’s proposed $400 million to $350 million on Oct. 19 and left out the convention center, over pleas to slow down from the hotel association and the union Unite Here Local 737 (Orlando Sentinel; Florida Politics; Central Florida Public Media). Voters choose up to six new members Nov. 3 as the board grows to nine (Orlando Sentinel).
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Two Florida power regulators took a hosts-paid West Palm Beach retreat; their commission takes up Duke’s data center rate Nov. 3
The Tampa Bay Times reports Commissioners Mike La Rosa and Bobby Payne blocked three July weekdays for the retreat, hosted by a GOPAC-tied group that won’t give a full donor list; the commission says no utility it regulates paid (Tampa Bay Times; The Washington Post). Duke’s docket, revised Oct. 20, sets its decision conference for Nov. 3, and no record ties any vote to the retreat (Florida Public Service Commission; WFTV).
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Brookfield’s Pembroke Lakes Mall fell to a $112M appraisal from $427M, and its lender sued to foreclose
KBRA says the $260 million loan went unpaid at its March 2025 maturity and estimates a $149 million loss to the bond trust; Deutsche Bank, as trustee, asked the Broward court for a receiver (KBRA; The Real Deal; Bisnow). Brookfield’s BGRE was not named in the suit and did not respond to Bisnow (The Real Deal; Bisnow).
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Plate III · Brightline’s junior Tampa bonds traded at about five cents on the dollar
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This edition, by desk
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Advertisement · Oaktree Reserve
The Weight of a Legacy
A Florida story. A present-day invitation to plan what follows.
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Watch the film · 0:30
John Ringling had approximately $300 cash on hand at his death in 1936; this was not his estate’s total value. His home and museum transferred to Florida in 1946 after years of estate administration.
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Historical source, imagery and transcript
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About
Old Florida Money is Oaktree Reserve’s public Florida capital brief: the named checks behind houses, teams, races, and public votes across the state.
Plates are drawn illustrations, charts or type, not photographs. Public figures appear only in caricature.
Drawn after reference photographs: Plate I, USDA Farm Service Agency, National Agriculture Imagery Program (NAIP) 2022, tile m_2608040_sw_17_030_20230213, via USGS The National Map (US government work, public domain). Plate II, Carol M. Highsmith, Carol M. Highsmith Archive, Library of Congress (LCCN2011631106), via Wikimedia Commons (public domain); Architect of the Capitol (official AOC photograph, USCapitol Flickr, Oct. 28, 2013), via Wikimedia Commons (US government work, public domain). St. Petersburg · Est. MMXXV
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