Caddy Confidential: What a Golf Bag Reveals About Power

Caddy Confidential: What Fits In A Golf Bag Reveals More About Influence Than A Lobbyist Report

Because sometimes access comes with a headcover and a wet towel.

An anonymous caddy's inventory, tournament receipts, and the contents of a presidential golf bag combined to make an airtight — and absurdly readable — dossier on influence that a 300‑page lobbyist report forgot to itemize: monograms, meal lines, and RSVP lists.

It was at the Capitol Greens Charity Invitational (a perfectly normal, mostly altruistic scramble, we are assured) where our uncredited source — a caddy who insisted on being named only as “Sam” because that sounds like a nice, untrustworthy caddy name — unloaded a bag and a lifetime of whispers.

"You learn more from a scorecard than you do from a press release," said Sam. "People write initials by pars now like they're signing M&A letters."

— Sam, Anonymous Caddy (requested a tip jar emoji in lieu of on‑the‑record testimony)

What Sam pulled from the bag read like a who's‑who of influence rebranded for the fairway:

• A leather scorecard holder with donors' initials scrawled next to each hole ("H.M. — Gala", "A.P. — Auction Lot 7").
• A stack of receipts in a ziploc labeled "Events" that included line items such as "Hospitality: Greens Fee — $28,000" and "Lunch/Networking — $1,750pp."
• A USB stick tucked inside a putter grip labeled "GUEST LISTS — DO NOT DELETE." (Sam's tech advice: "If they insist on a USB, assume they like handwritten promises.")
• A driver headcover embroidered with a private equity logo and the phrase "Repeat Player."
• Travel‑sized sunscreen stamped "PR SPF 50 — Smear‑Resistant Answers."

Receipts, Sam said, are where the theater becomes accounting. The charity ledger showed a single