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Plate I · Pensacola Beach Before Isaias
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The Lead · Storm money · Panhandle
Citizens Property Insurance has 9,052 policies and $3.56 billion of exposure in eight Panhandle coastal counties from Escambia to Wakulla, 4.8% of its book; the five under the Hurricane Warning hold $3.30 billion of it (Citizens’ Aug. 31 table; our sums). Brokers put the insured loss for the whole northern Gulf, not Florida alone, in the low to mid single-digit billions (Artemis; Insurance Business).
Hurricane Isaias was a 105 mph storm at 11 p.m. ET Oct. 8, the National Hurricane Center said, expected on the northern Gulf Coast late Friday or early Saturday, with a Hurricane Warning east to Florida’s Bay/Gulf County line (NHC Advisory 10). Its insured bill can reach any Florida policyholder: Citizens, the state-created insurer, has $3.56 billion of exposure in eight Panhandle coastal counties, and a shortfall can be billed statewide (Citizens). Your stake: the hurricane-deductible window opened with the 11 p.m. Wednesday warning; a 2% deductible is the first $2,000 per $100,000 of dwelling
coverage (Florida Statutes; our arithmetic). Assessments could reach nearly every property-casualty policy, auto included (Citizens); Citizens says its reinsurance covers a 1-in-360-year storm without them.
Old Florida Money desk · Fri Oct 9 · Written Thursday night; storm facts as of NHC Advisory 10 (11 p.m. ET Oct. 8) · Sources: National Hurricane Center; Citizens Property Insurance Corp.; Insurance Journal (Florida OIR data); Artemis; Insurance Business; Florida Statutes; Florida Hurricane Catastrophe Fund; Executive Office of the Governor; Escambia County; WJHG; FPL
Read the full story
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Plate II · The Sealed Compact
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Money Pulse
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The Seminole Tribe sued DraftKings and CEO Jason Robins on Oct. 8
The Tribe, whose compact payments from all its Florida games came to $1.04 billion last fiscal year, alleges in a Broward complaint that DraftKings’ Florida app is an illegal sportsbook and accuses Robins alone of racketeering. DraftKings says its prediction markets follow federal law and Pick6 is not sports betting.
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The Rays swept the Yankees; the $2.36B ballpark’s sales-tax hearing moved
Tampa Bay won 4-3 at Yankee Stadium on Oct. 7 and opens the ALCS Monday at Tropicana Field. The same day, Hillsborough commissioners voted 5-1 to move the hearing that must come before $360M of the county’s half-cent sales tax goes to the ballpark; no new date is set (Tampa Bay Times).
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Hope Florida’s $10M was “never public money,” an appeals court says
On Oct. 7 the 1st District Court of Appeal ordered the grand jury report on the Centene settlement money expunged; the ruling is not final. The two nonprofits that got Hope Florida’s grants gave $8.5M in October 2024 to Keep Florida Clean, whose chairperson of record is Attorney General James Uthmeier (Division of Elections).
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$165M: Larry Ellison’s North Palm Beach asking price, a local record
He paid $80M for the Seminole Landing estate in 2021 and quietly floated it at $145M the next year, with no takers (Robb Report). In Manalapan, his recorded $173M purchase of June 2022 covered the estate and an Intracoastal island parcel together (Property Appraiser).
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Brightline’s parent companies are in Chapter 11; the trains still run
Seventeen holding companies filed Sept. 24 over about $2.5B of debt. A judge approved up to $257.7M of rescue financing on an interim basis, with a final hearing Oct. 29, and bondholders committed about $490M of exit financing (court filings). The plan leaves muni principal in place but calls for deferred interest payments (The Bond Buyer).
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Donalds has raised eight times Jolly’s money; a new poll has them tied
Through Sept. 25, $134.4M to $16.7M across campaign and committee (News Service of Florida). St. Pete Polls had the race 45-45 on Oct. 5 to 7, and Mason-Dixon had Donalds up 48-41 from Sept. 28 to Oct. 1 (Florida Politics; NBC 6).
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Plate III · The Ball and the Dome
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This edition, by desk
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Who pays, and who answers for it. Isaias puts Citizens’ $3.56B of Panhandle exposure and the state’s assessment machinery in play. An appeals court calls Hope Florida’s $10M “never public money.” Byron Donalds has raised eight times Jolly’s money, and Brightline’s parent companies are in Chapter 11 while the trains run.
The Lead, above
Hope Florida grand jury report ordered erased; appeals court calls the $10M “never public money.” An IRS claim is still open
Byron Donalds has raised eight times Jolly’s money, and a new poll has them tied at 45
Brightline’s parent companies are in bankruptcy. The trains still run, and its bond insurer and muni funds are lining up $490M to see it through
Open the Politics desk
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Larry Ellison is asking a North Palm Beach record $165M for his Seminole Landing estate while he keeps assembling Manalapan. Florida Realtors are the only donor behind Vote Yes on 3, $18M, and two new polls put Amendment 3 under the 60 percent it needs.
Ellison and MacNeil split a Manalapan lot for $66.4M, then kept assembling
Florida Realtors are the only donor to the yes campaign on the homestead amendment, $18 million, and two new polls put it short of the 60 percent it needs
Open the Houses desk
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The Seminole Tribe sued DraftKings and its CEO over sports bets the Tribe says only it may take in Florida. The Rays swept the Yankees and open the ALCS Monday while Hillsborough reschedules the sales-tax hearing on their ballpark.
The Seminole Tribe sues DraftKings and accuses CEO Jason Robins of racketeering, calling its Florida app an illegal sportsbook
The Rays swept the Yankees. Hillsborough just moved the hearing on their sales-tax money
Open the Teams desk
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Forbes ranks Jeff Bezos Florida’s richest at about $378B, No. 2 in America. Several of the names behind him write the big PAC checks and own NFL teams.
Bezos is still Florida’s No. 1 at $378B; the Forbes 400 maps who moves Florida money
Open the People 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.
The aerial sequence is an AI-created interpretation, not recorded drone footage or a verified aerial survey. No family or museum endorsement is implied.
Historical source, imagery and transcript
Oaktree Reserve is not a law firm. Legal services are provided separately by Oaktree Reserve Law PLLC.
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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 painted illustrations, not depictions of the people named in the stories.
St. Petersburg · Est. MMXXV
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