(How to Win at Golf by Losing)
There are a lot of ways to gamble on golf.
Most of them are irresponsible. Some of them are illegal. And a few of them – like ours – are just irresponsible enough to matter, but not enough to ruin a friendship or trigger an IRS audit.
For the better part of a decade, I’ve been running a standing bet with a man known only as The Duck Hook King, Jason. (See – Notes from the Cart: Why Not Four Carts? For all the duck hooking details!)
Pick a golfer for a major. If your guy wins, you win the pot. Simple. Harmless.
Until no one wins.
Because when no one wins… the pot rolls over. And rolls over. And rolls over again.
After about a year and a half watching professional golfers not be the one guy we picked, the pot reached what I would describe as “I can’t tell my wife about this if I lose” kind of money.
So, like responsible adults, we made it more complicated.
Three picks per major. Two open. One dark horse at +5000 or worse. Lowest score wins. Your guy wins the tournament? 5x payout. (but no roll over!)
AND – We golf for first pick!
ENTER: MATCH PLAY FOR DRAFT POSITION
Last year we made a critical decision – which is to say, a mistake.
We decided “The Masters” draft order would be decided by get this playing golf! Nine holes. Match play. Loser picks second.
We chose Forest Lake in Ocoee. Convenient location. Open tee times. That perfect Florida window between work’s over and mosquito murder.
By hole four, Jason is 4 up. To be clear – he’s not awesome. He’s called Duck hook for crying out loud. I’m just sucking the joint up. He’s making sixes. I’m making sevens, eights, and one score still under investigation. He wins easily.
I shamefully and without pride will pick second.
THE DECISION
Our selections come the day before the tournaments start – so pins and needles the Wednesday before the Masters.
(There are no actual pins and needles. Scottie Scheffler has won approximately 783 of the last 784 tournaments.)
The real question: what do I do with pick number two?
Every gambling app on earth has Rory at second-best odds. But here’s the thing – I have conservatively taken Rory McIlroy fourteen times over the years of this bet nonsense. He’s won exactly zero times while wearing my jersey.
So what to do?
Xander? He’s got a Star Wars name.
Shane Lowry? Go full Irish and angry.
Morikawa? Handsome fella, smooth swing.
Oh no — I take Rory.
Not because I believed in him. Not because I thought the curse was lifted. Because I didn’t want Jason to have him. Pure spite.
AND THEN THE GOLF HAPPENS
As you are all now mostly aware (SPOILER ALERT!) in spite of my best efforts to sabotage his week with the selection, Rory friggen Mcllroy wins the 2025 Masters!! Every single Northern Irish person is in tears, parades, holidays, Guinness by the barrel for all! Rory Wins!
Annnnd Because I lost at golf, I have him. Sweet, stupid golf justice.
2026. WE RUN IT BACK.
Friday in March in Orlando – Perfect weather. Late afternoon start.
We grab a Hooligan Special of Miller Lites and we hit the tee box.
(That’s a bag of delight right there!)
Unlike last year – Where I was awful , and DHJ was slightly less bad – Both of us are miserable. Embarrassingly bad. Both shoot 50-something on the front. There are eights – plural. Water. Bushes. I produce a small colony of divots on the tee box. The tee box.
We trade doubles and triples for 9 holes, and are somehow tied. So we decide we’re so awesome, and so good at golf, lets amp it up and go sudden death. Works on TV, I’ve seen it!
10th hole. Weekday. Fading light. The subtle sound of my spanked dog off the tee.
AND
I lose. Again. He shot a 7, I shot an 8 (oh that’s karma)
WHICH BRINGS US BACK TO THE QUESTION
Masters week is almost here.
I pick second. Again. (No Scottie for me!)
Do I learn? Do I grow? Do I take Rory a fifteenth time on pure spite and blind superstition?
When the time comes, we’ll see.
But I’ll tell you this – spite has a better track record than my swing.
Life’s still great with an 8.