The Holiday Miracle at Cypress Point

How a $5 Tip Turned Into the Round of a Lifetime

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The Holiday Miracle at Cypress Point

The week before Christmas tends to soften even the sharpest elbows at private clubs. Maybe it’s the indoor trees and colorful lights. Maybe it’s the year-end bonuses. Or maybe it’s the faint hope that somewhere, somehow, karma is keeping score.

Longtime readers will remember Heaven’s Guest - the incredible tale of a dead bond trader who kept inviting clients to Cypress Point from beyond the grave. This year’s final CCC story has the same setting, the same impossible outcome, but for once the miracle didn’t come from mischief. It came from kindness.

Here’s how we heard it:

A group of friends had just wrapped up a holiday weekend at Pebble Beach. One of them, we’ll call him Mark, was not what you’d call a golf sicko. He played to an 18, owned one pair of golf shoes and believed that anything over four hours qualified as “a bit much.” He loved the game but did not obsess over it the way his buddies did.

Driving back to his hotel in Monterey, Mark pulled off at a small fruit stand on the side of the road. With unseasonably warm weather, he was in no hurry to be anywhere, so he asked the workers about their orchards, their kids and their holiday plans. He bought more fruit than he needed, tipped a little extra and told them to get something extra for los niños this year.

As he turned to leave, the man running the stand stopped him.

“Amigo,” he said, “how would you like to play Cypress Point tomorrow?”

Mark laughed, assuming it was a joke. It wasn’t. The man’s brother was a chef at Cypress. Staff get a few Monday rounds a year. His brother still had one left, unused and expiring before the calendar turned. He was going out anyway, and was allowed to bring a guest.

And, because Mark had taken an extra two minutes to treat him like a human being, that guest could be him.

Mark thanked him but still didn’t fully grasp the magnitude of what he’d been offered. It wasn’t until he returned to the hotel and casually mentioned it to his buddies, the true golf sickos, that the appropriate panic began. They surrounded him like medics on a battlefield.

“Call your wife. Change your flight. Cancel everything. You’re playing Cypress.”

He did. They lived vicariously through him. The next morning he walked the sacred ground of Alister MacKenzie’s coastline masterpiece. Ocean wind, perfect turf, the kind of beauty that makes even an 18-handicap feel like he’s floating. Nobody broke 100. Nobody cared.

He wasn't Heaven's Guest this time. Just the beneficiary of something much simpler - and much rarer: common decency.

So as the year comes to a close, consider this a gentle reminder: be kind, take the extra minute, tip a little more than you have to.

You never know who might be holding the most coveted invitation in golf.

Poll Question

What actually earned him the Cypress invite?

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Last Week's Poll Result

Every club has a Warren. Yours is usually:

🟨🟨🟨🟨⬜️⬜️ Pitching “alternative investments” between beers

🟨⬜️⬜️⬜️⬜️⬜️ Running a silent Ponzi on the staff

🟩🟩🟩🟩🟩🟩 Two months behind on dues and three months behind on reality

🟨⬜️⬜️⬜️⬜️⬜️ Living in a house technically owned by four banks and a widow

With all four types recieving votes, it looks like “Warrens” do truly come in all shapes and sizes, but behind on dues & reality seems to be the most common! Thank you for voting and especially to those who dropped a nice comment about the story - we love seeing them!

Don’t forget to catch up on past stories at ccconfidential.vip - and while you’re at it, tell a friend!

Next week lands on Christmas Day - but don’t worry, we’re still sending a little something your way: the return of Dear Caddie!

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