Betting Strategy: 'Sometimes you just have to eat the chalk to get through the sequence'

May 14th, 2022

Building tickets from the Horsemen’s Lounge with Kaitlin Free

After my first season as a public handicapper, I looked at my betting account and realized one thing: I need help. Picking 349 races, I had 97 winners (28%) with an ROI of $2.08. But after subtracting my action bets--tell ya what I was a kid in a candy store the first month--I had lost 15% on my personal bets. Clearly, I need to spend more time structuring my wagers. I will use this column to learn from people I respect about how to better express my opinions. We’ll take a card and a pool, and discuss betting strategies.

What began as Kaitlin Free's dream to become a professional jockey transformed into a burgeoning career as a handicapping expert. After her first meet as racing analyst at Turfway Park, Kaitlin has settled back into the paddock at Churchill Downs where she offers her picks, grabs connections for interviews, and helps bettors put together the last pieces of the puzzle. With a degree in Equine Health and Therapy from Hocking College, Kaitlin knows horses in ways many other horseplayers don’t. Partnering with Andy Villanueva, Kaitlin does (@GOATHandicappin)--check out their podcast GOAT ZOOM ROOM. As well, she writes and handicaps for X Factor Racing Group @x_factorracing. Proud winner of a 2017 Beemie Award for Best Twitter Hiatus, you know you can find her insights @kaitlinefree. 

Kevin Kilroy: When I listen to you in the paddock, you're really helping me narrow down my thoughts as I am about to put my bets in. Do you build tickets last minute with the information you are gathering?

Kaitlin Free: I do. Yesterday (May 13) is a perfect example. I really liked the 5 World Cruiser (in the seventh race at Churchill Downs), but Joe (Kristufek) and Scott (Shapiro) had their knocks, so that gave me pause. But as much as I looked at the horse in the paddock, I knew this horse looked the best and was winning no matter what. He came in at 6-1, which was a nice win play. Or in another race, there was a horse that Scott loved, but she looked bad in the paddock and I tossed her from my verticals.

Kilroy: The interviews you do with trainers and jockeys help me out too.

Free: Definitely, again yesterday talking with Al Stall about Masqueparade coming off the layoff and taking the blinkers off gave me confidence so I decided to build an exacta with my main opinion in the race, Major Fed.

Kilroy: So you're comfortable making edits to your wagers and firing away at the last minute?

Free: Yeah, so I’ll set up shop in the Horsemen’s Lounge, which is right around the corner from the paddock. It’s where the owners and trainers go, and so I set up there, listening and taking it all in, putting my bets together processing the last minute information.

Kilroy: Love it. What about for Churchill’s Saturday card?

Free: I put together a Late Pick 5. This is a tough card. 

Kilroy: What is it in this sequence that prompts you to play?

Free: Something has got to click for me to play the Pick 5, other than on big racing days where I know the pools will have value. But there are two singles in here for me, and some prices I am keen on in the other legs.

Kilroy: Do you use ABC constructions?

Free: Sometimes I do use ABCs, usually just on bigger race days when I spread more. But today I will only spread in a couple legs but take advantage of what I believe to be two singles here, so the ticket is affordable using all my selections. I can use the horses I want and the ticket won’t be too bad in here.

Kilroy: Take us through it.

Free: In Race 7, there’s four or five horses in here that I think have the opportunity to run well. A few of them are coming off the pace, which seems to have been doing well on the turf course. With Gaffalione and Brown, I have to give myself coverage on the #7 Arrobatic (7-2). I’ll use the #1 Walkathon (3-1). And the #8 Glenall (7-2). And the #10 Schlofmitz (10-1). I watched her a ton at Turfway. She got into a semi-bad situation in the Bourbonette, and she’s unbeaten when she is on Lasix. I think she can be a little bit closer to the front if she needs to be. I am definitely keen to use her. 

Kilroy: How about Race 8?

Free: Here I feel comfortable singling the #6 Quick to Blame (2-1). Coming out of MSW company with Ethereal Road and Call Me Midnight, he’ll be tough against these. The #7 Uncle Berley (3-1) is dangerous in here, too, especially with Asmussen getting back to it in Kentucky, but sometimes his horses do need a start before they run their best races. I do worry that both of these are hangers, but the 6 is standing out most to me, and I want to use just one.

Kilroy: Taking a stand on the 6 - nice. 

Free: In Race 9, #5 Twilight Gleaming (6-5) is head and shoulders the best horse in this race. But there is also other speed in here which could compromise her chances. Still, I can’t imagine not using her and it’s either toss or single, so I will single here. But #4 Boxing Day (15-1) scares me a little with the blinkers coming on for Walsh.

Kilroy: At this point are you thinking “I’ve got three favorites”?

Free: Yes, I am just trying to get through the first three legs, and I am going to take prices in the last two legs. But things have been chalky at Churchill, so I am keeping that in mind, too. In Race 10, I am going to take a couple 6-1 shots in here, and try to beat the favorite #5 Gerri B (3-1). #1 New Roo (6-1) has some sneaky Churchill form. Also the #3 Liberty M D (5-2) but who might go off as favorite so that gives me pause. But also #4 Remain Anonymous (6-1)

Kilroy: And who will you be alive to in the last leg?

Free: I am hoping that the #13 Treasure of War (15-1) gets in off the AE list. Cherie DeVaux is such a good trainer, and I think this horse will be best suited for this firm turf course and takes the blinkers off. I am also interested in the #11 Easy to Love (5-1) because Bill Mott is so good at getting them to turf when they need to be, though the pedigree doesn't scream turf to me. I am also going to take a shot with the #4 Chiromante (12-1). Probably a big ask, but at 12-1 for Brendan Walsh, I’ve got to include this Caravaggio out of a Danehill mare. If the 13 doesn't scratch in, then I will use the #3 Beachfront Bid (2-1).

Kilroy: I am trying to figure out how to bring some more tickets home, and you are doing something with this ticket that interests me. Sometimes I try to get too clever, too skinny when building my tickets. I get greedy trying to beat too many favorites and end up cashing fewer tickets, like last night at Evangeline Downs, I was alive in the Pick 5 to strong will-pays but the favorite won, who I was trying to beat more because of equity than because of opinion. You seem to be OK using favorites liberally.

Free: I think it depends on the races, the complexion of the sequence. From being at Churchill for a year now, unfortunately I know favorites come in often and are just part of it. Sometimes you just have to eat the chalk to get through the sequence. And then try to beat the ones who you really feel are bad favorites. It’s hard because the payouts aren't as big and the ticket gets more expensive, but I am keen to throw in some of the lukewarm favorites when I am seeing prices in other legs.

Kilroy: What about other pools beyond the Pick 5 - will you be playing verticals?

Free: I will definitely do verticals if I see something in the paddock. Like with Twilight Gleaming, I feel strongest about her, but it’s not a huge field so I don’t want to think about building a vertical ticket with her unless I see something that really grabs my attention in the paddock, a stand-out in the flesh or mannerisms that make me want to use them underneath. Then I will build a ticket if I think I am getting the right prices.