KEY WEST, Fla. — The political committee financing attacks against mayoral challenger Sam Kaufman and other candidates has increased its available war chest by nearly 46% after receiving a $17,000 infusion from a statewide Republican political committee with a long history of moving money among other PACs.
Families & Friends for the Keys, the committee chaired by Key West businessman and Conch athletics supporter Jack Niles, has now reported $68,278.08 in total receipts and $18,853.96 in expenditures, according to its latest Florida Division of Elections filings.
That leaves the committee with an estimated $49,424.12 available to spend during the closing days before Key West voters go to the polls Aug. 18.
The committee previously had $33,854.04 remaining after raising $51,270 and spending $17,415.96. Its available cash therefore increased by $15,570.08, or approximately 46%, during the latest reporting period.
Virtually all the new money came from a single source.
Florida Courage, a Gainesville-based political committee, contributed $17,000 on July 29. Another $8.08 came from interest paid by Centennial Bank.
The Florida Courage contribution is now the largest single check received by Families & Friends for the Keys, surpassing the $15,000 previously contributed by Spottswood Management. It represents nearly 25% of everything the Niles committee has raised.
Who Is Florida Courage? Why Key West?
Florida Courage is an active state political committee chaired, managed and represented by William Stafford Jones, a longtime Republican political operative from Gainesville. Jones is also listed as the committee’s treasurer and registered agent, according to the Florida Division of Elections.
Consider this: The PAC donated $100,000 to the election of gubernatorial candidate Byron Donalds; it donated $17,000 (nearly 20% of that total) to the re-election of an incumbent mayor in a city with a rural population.
The committee operates from 1722 NW 80th Blvd., Suite 90, in Gainesville—the same address associated with Jones and Alachua County Republican organizations. The Republican Party of Florida currently lists Jones as the Alachua County GOP’s state committeeman.
Jones is a former chairman of the Alachua County Republican Party and has controlled or helped operate a broad network of political committees that collect and redistribute money across Florida elections.
Who is Stafford Jones?
Florida Courage reported approximately $2.58 million in cumulative contributions and $1.31 million in expenditures through June 30, according to campaign-finance data compiled by Transparency USA.
A recent examination of Pasco County races described Jones as a longtime Republican operative and identified Florida Courage as a contributor to conservative candidates and committees. The Hernando Sun reported that the Jones-controlled PAC network has participated in county commission and school board contests around the state.
Florida Courage’s own money has come substantially from other political committees rather than directly from individual Key West voters.
Recent contributors have included:
Protecting Florida’s Progress: $352,000
Serious Conservatives: $200,000
Citizens Alliance for Florida’s Economy: $55,000
True Conservatives: $16,650
Protect Jax: $10,200
Utopia Lands Partnership: $10,000
Dynamic Group LLC: $10,000
John Cannon Homes: $5,000
That committee-to-committee movement creates another layer between the original donors and the political advertising ultimately reaching Key West voters.
Florida Courage has also transferred money to prominent Republican political operations elsewhere in Florida. Campaign disclosures show it contributed $100,000 to Friends of Wilton Simpson and another $100,000 to Friends of Byron Donalds during 2025.
Its $17,000 contribution to Families & Friends for the Keys marks its entry into the Key West municipal races.
More than 92% of the committee’s spending has gone to Green Point Group Corp., the Miami political consulting firm also paid $43,747.96 by incumbent Mayor Danise “DeeDee” Henriquez’s campaign.
Combined, Henriquez’s campaign and the Niles-controlled committee have paid Green Point Group $61,142.82 during the same election cycle.
Families & Friends for the Keys has used its money for text messages and direct-mail pieces attacking Kaufman while promoting an establishment-aligned slate of candidates. Henriquez has not publicly disavowed the committee’s attacks.
Before Florida Courage entered the picture, the committee’s money came largely from Key West tourism, lodging, cruise-industry and development interests, including Historic Tours of America, the Walsh family’s Key West hotels, Spottswood Management and developer Jeffery Cornfeld.
The latest filing brings a statewide Republican PAC network—and another $17,000—into a municipal contest already shaping up as one of the most expensive and bitterly fought elections in Key West history.
With $49,424.12 still available and early voting continuing through Aug. 15, the committee now has nearly three times as much money remaining as it has reported spending on the advertising campaign to date.
Editor’s note: Contribution and expenditure figures were calculated from reports filed with the Florida Division of Elections. Cash available is estimated by subtracting reported expenditures from reported receipts and does not account for unreported obligations or expenditures incurred after the latest filing.
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Follow the money! Underhanded dealings, opaqueness throughout. Thanks for bring this to light