Fandom, Emotional Swings and Sharp Bets

Today’s newsletter will be a little different - should be a fun one!

I’ve mentioned before that I went to college at the University of Wisconsin (go Badgers), but have also been a longtime fan of University of Illinois basketball.

These are the two teams I follow most closely, and they faced each other in a wild game Tuesday night with the Badgers prevailing in OT.

Here’s the win probability chart through both halves and overtime:

My deep familiarity with both teams and total focus on the game opened up a betting/trading angle I did really well with (made $2,000 with only a fraction at risk).

Today I’ll share the story as well as my approach and reasoning. Hopefully you can find similar opportunities through teams you follow most closely.

As always, we’ll keep our winning ways going and close with this week’s Bets of the Week!

Let’s get after it.

Background

Illinois:

Illinois was playing at home and came into the game favored by 10.5 points. They had won 12 of their last 13 games and had the KenPom #1 rated offense in college basketball.

They were, however, missing two of their top three scorers: guard Kylan Boswell and forward Andrej Stojakovic.

When fully healthy, the Illini have eight strong players in rotation.

I was curious if they’d shorten their rotation to the six healthy “strong” players (which could lead to exhaustion), or give more time to players at the end of their bench.

Wisconsin:

Wisconsin was having a comparatively weaker season, sitting barely inside the KenPom top 40 prior to the game and on the bubble of making the NCAA Tournament.

Their season highlight was being the only team to beat #2 ranked Michigan, and they did so on the road. So they’d shown potential to unseat more talented squads.

My investment:

Personally, I love both teams - I watch 75% of their games!

But in situations like this my default fan support goes to the Illini.

Let’s get to the game.

Game Progression

A back and forth first half concluded with Illinois leading by six points.

I made my key betting observation, however:

Illinois was only playing six players.

And only one of those six players was a confident ball handler: freshman phenom Keaton Wagler.

While Wagler was playing well, and Illinois was shooting well from the arc, the 6-man rotation put tremendous pressure on their young star.

In addition, Wisconsin’s upperclassman guards were able to penetrate and score effectively against the depleted (and slow) healthy Illini.

Though Illinois carried a big lead down the stretch (as many as 12 points), they felt vulnerable and tired.

Here’s how I played that read.

Bets/Trades

I made three “trades” on Kalshi during the game.

Here are the timestamps and specifics:

My initial bet: $464 on Wisconsin moneyline at +790 (would pay out $4,140).

I made this bet during a timeout with 4 minutes left in the game and Illinois leading by 5.

I did not think the algorithms driving that price appreciated the comparative exhaustion the Illini would be dealing with, and I saw their offensive possessions and rebounding declining.

My first trade out: I sold about 30% of my position at 3x the initial value, recouping $423.

I made this “sale” during a timeout with 1 minute left and Illinois leading by 2.

This was an emotional decision! I wanted to root for the Illini, but capture some value from being “right” in the event Wisconsin didn’t finish their comeback.

My final trade out: I sold another 20% of my initial position at 7x the initial value, profiting $652.

I made this sale with 3 minutes remaining in overtime and Wisconsin leading by 6.

I felt the price was fair value.

Overall PnL: Wisconsin ended up winning the game in OT, leading me to a net profit on the bet of $2,612.

I was disappointed, but my bankroll had grown.

Three Takeaways from this Experience for Your Betting:

1. If you’re highly invested in a team, notice when something unusual is happening that a computer algorithm or trader may miss. In this instance, I trusted my read about the impact of Illinois’ short rotation.

2. Make sure your observation includes a factual special situation, and not anecdotal bias. The 6-man rotation Illinois deployed was a fact. So I had a credible cause for my read. Thinking “such and such player looks tired” would not qualify.

3. Don’t be shy about taking profit or exiting your bet if it’s interfering with your rooting interest! I tried to be up front about the fact some of my bets were emotional decisions. While I generally steer people toward analytical rigor, if you’re not compromising much value, don’t ruin your fan experience!

Hope that was helpful, let’s get to this week’s betting!

Bet(s) of the Week $$

Last week our Super Bowl bets made some cash!

We went 3-1, with the following outcomes

• Over 45.5 points for 0.5 units - LOSS

• Kayshon Boutte longest reception over 17.5 yards for 0.5 units - WIN

• Rhamondre Stevenson under 53.5 rush yards for 0.5 units - WIN

• Drake Maye over 35.5 rush yards for 0.5 units - WIN

In total, we won 0.96 units and have reached a new high water mark for newsletter bets!

Since starting the newsletter, bets in this section are ahead 24.11 units, with a positive 16% ROI.

A $100 bettor would be ahead $2,411 following these bets!

Based on my research, I am making the following bet this week:

• UT Martin +1.5 @ -110 on Caesars for 0.5 units (Tonight)

UT-Martin can lock up a top 2 seed in the OVCT, but a loss would open the door for 5-loss teams, which includes their opponent Lindenwood.

In their first matchup Lindenwood was heavily denied the rim by the Skyhawks' double teams. I don’t think they have the spacing to prevail against this defensive matchup.

Please fill out the survey about today’s newsletter and let me know your thoughts!