A second book by The Mad Caddy
Letters from the Loop
A book about golf, brotherhood, and the joy of carrying someone else’s bag.
Written by a caddie. For the players, dreamers, brothers, and friends who’ve ever picked up someone else’s bag — literal or otherwise.

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Letters from the Loopis a collection of letters from inside the game — written from the loop, the practice tee, the bag, and the back of a golf cart headed to the next hole.
It isn’t a how-to. It’s a why-to.
It’s about the brother who’d pack his suitcase before you finished the sentence. The quiet joy of working for someone else’s score. The dream that’s too big to defend, so you stop defending it.
For every golfer who’s ever:
- Said “I’ll be on the bag” and meant it
- Wondered if the world measures the right things
- Wanted to make the climb with someone they love, not alone
An excerpt — Letter 6: Augusta
Dear Brother,
I don’t remember exactly when we started saying it.
Maybe after one too many rounds where one of us hit a shot that looked a lot better in our imagination than it did in the air.
One of us would laugh and say, “I’ll see you at Augusta.”
The other would answer, “Yeah. I’ll be on the bag.”
It became our joke.
Not because either of us thought we were actually headed to the Masters.
Because every pair of brothers needs a dream that’s too big to defend.
We’ve said it enough over the years that I don’t even smile anymore when it comes up. I just answer automatically.
“You make it first, I’ll carry.”
“You make it first, I’m on the bag.”
No negotiations. No questions. Just a promise.
The funny thing is, I think we’ve both always meant it. Not the Masters part. The bag.
If tomorrow someone called and told me you’d somehow found yourself standing on the first tee at Augusta National, I’d have my suitcase packed before they finished the sentence.
I’d carry every club. I’d rake every bunker. I’d walk every yard.
Not because it’s Augusta. Because it’s you.
I’ve thought about why that little joke has stayed with me. Maybe it’s because it says something neither of us has ever had to say out loud. We’re pulling for each other. Not in the polite way people say they are. In the costly way. The kind that asks, If your moment comes before mine, can I celebrate it as if it were my own?
That’s a harder question than most people realize. The world teaches us to compare. Your promotion somehow diminishes mine. Your success delays my success. Your recognition means there is less recognition left for me.
Golf can be like that, too. You spend enough time around scoreboards and it’s easy to forget that someone else’s birdie doesn’t make your par any worse.
I’ve been trying to unlearn that way of thinking. Maybe that’s another reason I love caddying. By definition, I’m working for someone else’s score. When they hit a great shot, I don’t feel invisible. I feel grateful that I got to be part of it. There’s a quiet joy in helping someone else become who they’re capable of becoming. I wish more people knew that feeling. It’s addictive.
Sometimes I wonder what heaven measures. I doubt it’s trophies. I doubt it’s followers or titles or net worth. Maybe it’s the number of times you sincerely hoped another person would flourish. Maybe it’s every unseen act of encouragement. Every door held open. Every burden shared. Every bag carried.
If that’s true, then our little Augusta joke isn’t really about golf at all. It’s about the kind of men we hope to become.
The older I get, the less interested I am in standing on top of the mountain by myself. If I ever make it somewhere worth going, I hope I can look over and see someone I love making the climb with me.
And if you happen to get there first, don’t worry about looking for a caddie. I’ll already be waiting on the first tee.
Your brother,
B
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