The $70 Win: What a Barely-Green Stanley Cup Basket Taught Me About Winner-Take-All Markets

I made about $70 on the 2026 Stanley Cup.

Not $70,000. Sixty-eight dollars and twenty-eight cents, to be exact, on $2,332 spread across nine teams and held through an entire NHL playoff run. Call it 3%. I know how that sounds. But this was one of my cleaner trades of the year, and I have the full trade log to prove it, because the same summer I ran the exact opposite playbook on the World Cup and it cost me real money. We'll get to that.

The Plan: Try to Get Lucky, Bank It If I Don't

I announced this basket live on Episode 7, so the core of it's on the record: six of the top seven teams by price (everyone except Edmonton) plus Boston as a longshot, 11 units, and a warning that I'd probably live trade it a little. I did. By the end I'd also picked up Dallas and Montreal on dips, and the full book came to $2,332 across nine teams. The scorecard tracks the official 11-unit version I announced on air; the table below is the whole book, every fill included.

Here's the part that matters: this was never an equal-shares basket. The structure had two jobs. The cheap legs were the get-lucky tickets. I loaded Buffalo at an average of 6 cents, Vegas at 9, Boston at a cent and a half. If any of those ran the table, this post has a much bigger number in the title (Buffalo winning paid me $6,638; Boston, $5,218). Carolina was the hedge: the most expensive team in my book at 23 cents, bought precisely so a boring, likely outcome still paid me something. Swinging for the fences and wearing a helmet at the same time.

Pricing came from the same process I use everywhere else: pull every market price, compare against a model (for hockey that's MoneyPuck, which prices playoff advancement very differently from the books), and buy where the market looks fair or cheap. One more thing from that comparison, and I said this on the tape in April: Colorado looked overpriced the entire time. The sportsbooks had them way above what the model said they were worth. So I bought a piece for coverage, flipped out of the entire position as the price held up, and banked a whole $9 profit on them. They went out without a Cup. Called it. (Funny detail from the trade log: because I'd sold out completely, Colorado winning would have actually cost me $782. Sometimes being right pays you nine dollars and saves you eight hundred.)

The Scoreboard

Team	$ in	Avg entry	What happened	Net	If they'd won the Cup
Carolina	$585.50	23.0¢	Won the Cup (trimmed into the run)	+$1,284.50	+$68 (this timeline)
Vegas	$458.58	9.1¢	Lost the final; sold some on the way	-$253.58	+$3,771
Buffalo	$450.25	6.1¢	Held to zero	-$450.25	+$6,638
Tampa Bay	$216.11	14.1¢	Held to zero	-$216.11	+$755
Colorado	$209.70	23.3¢	Traded out entirely (overpriced)	+$9.00	-$782 (already out)
Minnesota	$199.98	4.8¢	Held to zero	-$199.98	+$3,361
Dallas	$100.60	6.3¢	Traded out green	+$5.80	-$782 (already out)
Boston	$90.85	1.5¢	Held to zero	-$90.85	+$5,218
Montreal	$20.24	2.6¢	Held to zero	-$20.24	-$3
Book	$2,331.81			+$68.28

Every number above is from my actual Polymarket fills (324 trades, reconciled). The "if they'd won" column assumes I hold each team's final share count to resolution.

And yes, Carolina beat Vegas in the final. One of my tickets redeemed at a dollar while another of my tickets died in the same series. Past a certain round of a basket, you're guaranteed to be rooting against yourself somewhere. You get used to it.

Why $70 Is a Win and Not a Waste of Time

In a winner-take-all market you don't get paid for being right. You get paid for structure. Only one team lifts the Cup, so most of your tickets are guaranteed to go to zero. That's not a bug, that's the whole game. The question is never "how many did I get wrong?" It's "did the one I got right pay for all the ones I got wrong, plus a little?"

Mine did. And because it was the hedge that hit rather than a jackpot leg, I got the floor outcome, not the ceiling. Look at that last column again: Buffalo winning was worth $6,638 to me, Boston $5,218, Vegas $3,771. Carolina winning was worth $68. The market handed me the single worst champion still alive in my book, and the structure still finished green. That's what a floor is for. If Buffalo had won I'd be writing a very different (much more obnoxious) post.

The Move That Actually Mattered

The other thing that saved this trade is what I did with Carolina on the way up, and it's a barbell most people get wrong in both directions.

Some people sell the whole position the second it doubles. They feel smart right up until the team wins the Cup and they're holding nothing. Others hold every share to the end "because it's going to win," and then it loses a Game 7 and a paper fortune evaporates.

Do both at once. I bought 2,546 Carolina shares at an average of 23 cents ($585.50 all in). As they climbed through the playoffs I sold roughly two-thirds of the position into strength for $1,020, which returned my entire cost basis plus a profit before the final was even decided. The last 850 shares rode to the buzzer and redeemed at a dollar each: another $850. Trim into strength to de-risk. Keep a residual to catch the settlement. You get the run and the resolution instead of picking one.

It's the same move that turned my Arizona March Madness ticket into a profit on a team that never won anything. On a prediction market, the exit is part of the trade.

The Contrast That Stings

Now the confession, because the mirror image happened the same summer on the World Cup, and I have nobody to blame but myself.

My official podcast bet was Belgium, which died quietly for 2 units. Fine. But in my personal book I was long Argentina. Heavily. And when Spain kept getting stronger I had a clean chance to hedge across and lock in about a 10-unit profit no matter who won. I didn't take it, because if Argentina won I stood to make around 90 units, and I decided the story was worth the gamble. I literally extended my flight in the US to watch it happen. Spain won 1-0. I'm still having Claude tally the exact damage, which tells you everything you need to know, but it's somewhere in the 30-to-40-unit range.

Meanwhile Andrew ran the boring playbook on the same tournament: built a basket of favorites, accidentally ended up heavy on Spain, sold into the run, freerolled the rest, and walked away with a tidy profit on the champion. I hate it when he does that.

Same markets. Same summer. Same guy (me) running both strategies. The hockey basket banked $70 and the soccer book donated 30-plus units to people more disciplined than I was that week. One of these approaches is repeatable, and it's not the one with the better story.

Hear the basket announced live on Episode 7, along with the World Cup field-betting strategy and the Masters postmortem. The full results are on the scorecard.