In The Money Players' Newsletter

In The Money Players' Newsletter

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In The Money Players' Newsletter
In The Money Players' Newsletter
The Crossover - Oaks and Derby Edition

The Crossover - Oaks and Derby Edition

Spot Plays on Sports and Horse Racing

Apr 30, 2025
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In The Money Players' Newsletter
In The Money Players' Newsletter
The Crossover - Oaks and Derby Edition
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The Crossover returns with a look at the PGA TOUR and, of course, Oaks and Derby Day.

You’ll read, watch, and listen to a lot of content this week, but I doubt many will try to make the case for a 200-1 shot…We’ve got one in here.

Bourbon Raffle:

Before we begin the analysis, I want to inform you about a Bourbon Raffle that will take place just before the Kentucky Derby. I assume the Venn Diagram of Horseplayers and Bourbon drinkers/collectors has a significant overlap - that’s the primary reason I’m sharing this.

My son is part of a 12U Baseball Team heading to Cooperstown Dreams Park in June. The Bourbon Raffle is our primary fundraiser to decrease the cost for the players. This is legit, licensed, and follows all Kentucky Raffle and Charity regulations. All ticket sales go directly to the team, and the expenses for this trip.

If you’re interested in buying a ticket, simply reply to this email, and I’ll get you set up.

The drawing will be on Saturday and should be streamed on the Longhorns Facebook Page. If you’re in the Northern Kentucky / Lexington / Louisville area, I’ll personally deliver any winnings. For others, I’ll find a way to safely ship. Any support is appreciated!

*** At the time of writing, we’ve sold right around 100 tickets, which means this is shaping up to be an overlay (for raffle ticket holders) relative to our initial assumptions!


CJ Cup Byron Nelson

Let’s start with some golf. I’ve written about the parallels between golf and horse racing before. I’ve also been pretty open that much of my bankroll has shifted from Horse Racing to Golf for various reasons. So even though it’s Derby Week, I went through my process and figured I’d share some of my analysis.

The CJ Cup Byron Nelson is played at TPC Craig Ranch, the third-longest regular course on the TOUR following some tee box renovations. The rough was switched from Bermuda to Ryegrass (longer, too), and the fairways were switched from Zoysia to Ryegrass. As a result, I’m downplaying course history since the agronomy has changed considerably. You wouldn’t expect horses that love the GP dirt to necessarily take to the GP Tapeta the same way - same concept here.

I create a custom Mixed Condition model each week using the tools at Betsperts. What I include and relative weights change based on the field, course, conditions, etc. You can see what I’m looking at for this event below.

The area is expected to get a lot of rain, specifically on Wednesday. This puts an even bigger premium on distance (specifically Carry Distance) and likely means that approach play (iron shots, typically into the green) will be the separator. Putting on these greens has historically been relatively easy. I’ll find players who are better ball strikers and then look for signs they could spike with the putter.

Model Parameters:

Strokes Gained Total (Long Course, Easy Scoring, Bent Grass Greens)

Scoring: Birdie or Better

Good Drive %

Carry Distance

Apex Height

Strokes Gained Approach (Long Course, Easy Scoring)

Approach Proximity (200+ Yards)

Scoring: Par 4 Birdie or Better %

Scoring: Par 3

Strokes Gained Putting (Bentgrass)

Based on my modeling, the following guys are the ones that I’m targeting for Outright Wagers this week:

Joseph Bramlett (+22000): Bramlett ranks third in my model behind Taylor Pendrith and Scottie Scheffler. He’s a bomber off the tee and ranks number one in Approach from 200+ yards. Generally speaking, he can’t putt. That said, his putter is trending in the right direction and has some solid history here (specifically on the greens). Of note, he’s +450 to finish T20 - Solid value.

Gary Woodland (+9000): Woodland also models well, primarily driven by his top ranking with his Approach play. His Off the Tee stats are interesting. He’s not accurate off the tee, is middle of the pack in distance, and is in the top quartile in Carry Distance. So, he will be more than fine at a golf course that doesn’t penalize wayward drives and will likely reward Carry Distance. Woodland is always a solid putter, but he’s had spike weeks on this course in the past (2015-2017 specifically). He seems very live, and his recent T2 at the Houston Open shows he’s fully recovered and ready to contend.

Jake Knapp (+5500): Knapp is a tremendous ball striker who is a very capable putter. He’s played solid most of this year, fares well at courses that are forgiving off the tee, and finished eighth in his lone start here last year. The main knock would be his apex height, as he does his damage with a low ball flight.

Taylor Pendrith (+3000): Pendrith ranked best in my model this week despite not accounting for specific course history. He played the event for the first time last year and walked away with the top prize. He’s awful Around The Green, and this place can mask that weakness, assuming you are long off the tee and can putt. He can do both very well.

You may notice that Scottie Scheffler, the best second-best player in the world and a +280 favorite, isn’t on this list. I’m a huge Scottie fan, and despite his poor track record in this event (by his standards), he’s clearly the most likely winner. Scottie has been going left (off the tee specifically) this year, and it’s cost him in several spots - this won’t be one, and that’s a good thing. Still, while Scottie can go low, his advantage relative to the field is diminished on courses with easy scoring conditions.

If you’re convinced Scottie can win, there’s a way to create more value using the placement markets. Of the four golfers above, I view Pendrith as the safest play. I might also consider the following wagers using Scheffler and Pendrith as Keys.

Scottie Winner - Pendrith T20 - Bramlett T20 = +4700

Scottie Winner - Pendrith T20 - Woodland T20 = +3000

Scottie Winner - Pendrith T20 - Knapp T20 = +2600

Now we are in a place where we have some wagers that we can “dutch” and try to extract a similar amount from the Tournament, assuming one of our wagers hits. I use the following to illustrate what I mean:

The general approach I take with golf is that I’m trying to risk 1 Unit total to win 10 Units. This card violates that, as I’m trying to wager $100 and return $1,000. So, I have to be comfortable wagering more, or I will remove something from the card. Also, it’s possible that all of the Scottie tickets could cash, so I adjusted the payout expectation (and corresponding wager amount) accordingly.

Let’s hope we have a few sweats going into Sunday following a great Oaks and Derby Day.


Kentucky Oaks Day:

Race 1: 4-CHASTEN seemed destined for the Oaks trail but hasn’t been seen since her off-the-board finish in the Silverbulletday Stakes in January. Her running line has me wondering if she might have bled in that race? Especially since she shows up here with Lasix. The only fillies to have beaten her will all be taking their shot in the Kentucky Oaks. Her last work was solid; she gets a couple of pounds from a couple of foes, and anything better than 6/5 is probably value. Based on the connections that might be wishful thinking.

The risk is that she’s forced to chase the filly to her inside 3-SHRED THE GNAR. The Lynch runner has a tactical edge on this field and exits a key race. At first glance, trainer Brian Lynch has some gaudy stats with this move. In the Past 5 Years at CD, on Dirt, with last out winners: 5/18 (28%) with a $4.49 ROI. However, if you focus on route races, he’s 0/9 with 44% ITM.

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