BREAKING: Shadow PAC’s Largest Donation Yet: Spottswood Companies Gives $15,000 to Fund Attack Campaign Against Kaufman and Bolster Henriquez
Niles-controlled shadow PAC receives biggest single contribution from one of Key West’s most powerful development families as voters continue to complain about unwanted texts and glossy mailers.
KEY WEST — There is no relief in sight for hundreds and possibly thousands of pissed off voters in the Southernmost City who are sick and tired of receiving unwanted text messages and slick four-color glossy mailers attacking Commissioner and mayoral candidate Sam Kaufman while attempting to bolster incumbent Mayor Danise Henriquez.
The latest campaign finance filings show Spottswood Companies — one of the most powerful and politically connected family-owned businesses in the Florida Keys — donated $15,000 to Families & Friends for the Keys, the shadowy political action committee controlled by Conch athletic supporter Jack Niles.
It is the largest single donation the PAC has received.
The contribution from Spottswood Companies dwarfs the PAC’s previous largest donation — a $10,000 contribution from Historic Tours of America, owned by Ed Swift and partner Chris Belland — and signals a significant escalation of big-money interests bankrolling the shadow campaign against Kaufman.
Above the Fold previously reported on the PAC’s escalation from unsolicited smear texts to professionally produced glossy mailers, and on evidence suggesting illegal coordination between the Henriquez campaign and the Niles-controlled PAC.
The mayor has yet to disavow the smear campaign aimed at her opponent.
WHO ARE THE SPOTTSWOODS?
Spottswood Companies Inc. and its affiliates are a diversified, family-owned organization headquartered at 506 Fleming St. in Key West with investments in real estate, timesharing, marinas, hospitality, construction, broadcasting and banking.
The company traces its roots in Key West to 1836, making it one of the longest-established family enterprises in the Florida Keys.
Founded in 1992 by Robert A. Spottswood, the company has grown into one of the Keys’ largest private employers with more than 300 employees and over 1,000 hotel rooms under management. The company has developed dozens of properties in the Florida Keys with more than 1,000 residential and transient units and over 300,000 square feet of commercial space.
The Spottswood family’s reach extends well beyond real estate. Members hold positions on the South Florida Water Management District, the Citizens Property Insurance Corp. board of governors, the South Atlantic Fishery Management Council, the Nature Conservancy, the Fish and Wildlife Foundation of Florida and the board of First State Bank of the Florida Keys. Robert A. Spottswood Jr. was appointed by Gov. Ron DeSantis to the South Florida Water Management District board in March 2026.
The family also operates Spottswood, Spottswood, Spottswood & Sterling PLLC, a law firm at 500 Fleming St. that handles real estate and environmental land use law. Mary Spottswood serves as in-house counsel for Spottswood Companies, and Erica Sterling, a partner at the firm, was appointed by DeSantis to the Lower Florida Keys Hospital District Board.
SPOTTSWOOD MANAGEMENT TEAM MEMBERS
The following members of the company’s management team carry the Spottswood name:
Robert A. Spottswood, Executive Chairman
Born in Key West, graduated from Key West High School, the University of Florida and the University of Miami School of Law. Founded Spottswood Companies in 1992 after returning from Miami where he specialized in corporate law and made investments in real estate, banking and broadcasting. Responsible for creating the Hyatt Vacation Club and developing numerous timeshare, hotel and commercial properties. Serves on the board of First State Bank, the Florida Council of 100 and the Citizens Property Insurance Board of Governors. Past chairman of the Florida Fish and Wildlife Conservation Commission and the American Resort Development Association.
Robert A. Spottswood Jr., President and CEO
Seventh-generation Key West native. Also serves as President of Keystar Inc. and Spottswood Management Inc. Partner at Spottswood, Spottswood, Spottswood & Sterling. Member of the board of First State Bank. Appointed by DeSantis to the South Florida Water Management District board (2026) and is a member of the South Atlantic Fishery Management Council, the Nature Conservancy and the Fish and Wildlife Foundation of Florida.
Vice President/Director of Spottswood Companies and Executive Chairman of First State Bank. Known as Jack Spottswood. Graduated from Tulane University and Florida State University Law School. Founder and senior partner of Spottswood, Spottswood, Spottswood & Sterling. Former counsel for the Housing Authority of the City of Key West, former Assistant City Attorney, former Vice Chairman of the Key West Redevelopment Agency and a past Commodore of the Key West Yacht Club.
Director of Keystar Inc.. and Director of Spottswood Companies. Of Counsel to the family law firm. Graduated from the University of Florida and Florida State University Law School. Oversaw the development approval process for all Spottswood properties. Former chairman of the Key West Red Cross, the Key West Military Affairs Committee, past Commodore of the Key West Yacht Club and founding member of the Key West Police Athletic League.
Chief Development Officer for Spottswood Hotels Inc. and President of Key West Vacation Company. Native of Key West, graduated from Key West High School and the University of Florida. Attorney with a background in finance and real estate development. Vice President of the Key West Chamber of Commerce board of directors.
According to the company’s website, Spottswood Companies owns all or some interest in the following properties in the Island City and the Florida Keys:
Stock Island Yacht Club & Marina
Overseas Market Shopping Plaza
Banana Republic Key West Building
Crazy Shirts Key West Building
Key West Drug Company Building
The Bottling Court Retail Center
Faro Blanco Resort & Yacht Club, Marathon
Holiday Inn Express & Suites Marathon (rebranded)
THE PAC’S MONEY TRAIL
The $15,000 Spottswood Companies donation brings the PAC’s total war chest to more than $36,000. Previous donors include Historic Tours of America ($10,000), Hollywood-based real estate developer Jeffry Cornfeld ($10,000), Planning Board member Michael Browning ($500), Denise Holland-Schmitt ($520) and Bobby Mongelli ($250).
Cornfeld’s donation carries its own baggage. The developer was behind the Peary Court deal in which a former City Commission handed him $12.5 million to purchase the property with promises to create affordable housing and expand the project by 44 units — promises that never came to fruition.
Despite collecting tens of thousands of dollars, the PAC previously reported only $21.10 in expenditures — a payment to ABETON, an online donation-processing service — even as voters received wave after wave of text messages and glossy mailers. Professional four-color mailers, including design, printing and bulk postage, cost thousands of dollars, and any such expenditures must be disclosed in filings with the Florida Division of Elections.
Under Florida Statute 106.19, any campaign treasurer or PAC officer who knowingly and willfully fails to report expenditures commits a first-degree misdemeanor punishable by up to one year in jail and a $1,000 fine per count, plus a civil penalty of three times the amount of unreported spending.Voters head to the polls Aug. 18.
This is an evolving story. Watch this space.
Ed. Note: This content is not affiliated with, authorized by, endorsed by or produced on behalf of any candidate, campaign or political committee in Monroe County.