She Asked For a Transfer and Three Members Resigned in Protest
We’re not saying the country club drama at Whispering Palms in Naples, Florida was entirely about Jessica — 29, second-year caddie, criminally underrated club recommender — but when management reassigned her to the private member sessions and off the public tee times, three paying members handed in their resignation letters within forty-eight hours. One of them had been a member since 1997. (His wife was completely fine with the resignation. She had her own theories about why he’d been playing 36 holes every Saturday.) Jessica, who was working on a paralegal certificate at night, found the whole situation mildly hilarious. She kept the tip she’d earned that final morning — $450, which she said was “a reasonable apology.” The transfer was reversed within a week.
The First Thing She Said Was Club Advice. The Second Thing Caused a Divorce.
To be clear, Anna — 23, originally from Kyiv, now living in Miami and caddying at Brickell Bay Golf Club on weekends — did absolutely nothing wrong. She showed up, did her job, gave genuinely excellent yardage reads, and suggested a draw into the wind on hole 14 that was, by all accounts, technically correct. What happened next was between one Craig Harrington, 48, of Coral Gables, and his own conscience. (And eventually his wife, and then his wife’s attorney, and then a very thorough discovery process.) Anna does not know Craig’s last name. She doesn’t especially want to. She got a full-time caddie coordinator position at the club shortly after, which, all things considered, worked out better than fine — but that’s not even the most dramatic caddie story from that course that summer.
