Betting Guide For The 144th Kentucky Derby

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Betting guide for the 144th Kentucky Derby
Chris Fallica
ESPN INSIDER

The Kentucky Derby is one of the year's biggest handicapping events. Whether you are there for the party or you're an avid horse player, everyone is searching for a winner. Here are some of my thoughts from a betting perspective as the 2018 Derby approaches.All odds courtesy of kentuckyderby.com, as of May 1.

The field

1. Firenze Fire (Paco Lopez/Jason Servis) -- 50-1I was happy to cash tickets on him as a 2-year-old at double-digit odds in both the Sanford and Champagne, but his 3-year-old form leaves a lot to be desired, and the rail draw means he's got to be either first or last out of the gate. I'm glad a throw-out entry drew the rail so a real contender didn't get stuck there. Firenze Fire is not even worth using underneath.

2. Free Drop Billy (Robby Albarado/Dale Romans) -- 30-1He broke maiden at first asking over the Churchill surface last June and has run well in graded stakes, notably winning the Breeders' Futurity at Keeneland last year. But he's kind of flattened out as a 3-year-old. He'll be the biggest price he's ever been -- he's never been longer than 8-1 -- and Dale Romans has hit the board before with longshot runners. He'll get shuffled back because of Post 2 and do his running late. I'll use him in the lower rungs of tris and supers, but he can't win.

3. Promises Fulfilled (Corey Lanerie/Dale Romans) -- 30-1A $40 upset winner over Good Magic at the Fountain of Youth on a speed-favoring Gulfstream surface, Promises Fulfilled will be seen early as a pace factor. Watch him back up late, but he isn't worth inclusion.

4. Flameaway (Jose Lezcano/Mark Casse) -- 30-1He's a five-time winner, but one of those wins was on turf, one was on synthetic at Woodbine and two came in washed-off-the turf events. He held off Catholic Boy and Vino Rosso at Tampa, but he's nothing more than a pace-setter here. I'm not using him at all.

5. Audible (Javier Castellano/Todd Pletcher) -- 8-1The visually impressive winner of both the Holy Bull and Florida Derby at Gulfstream is one of four Todd Pletcher trainees attempting to give the trainer a second straight Derby win. Pletcher would be the first trainer since Bob Baffert in 1997-98 to do just that. Audible is proven to be a versatile type, winning from the lead, just off the lead and well off the lead. But I wonder how far he really wants to go. Ten furlongs might be asking a bit much. Javier Castellano hasn't fared well at the Derby, as only Normandy Invasion finished better than sixth in his 11 career mounts. In fact, he's the only jockey in Derby history to have at least 11 mounts and not have an in-the-money finish. While he chose Audible over Bolt d'Oro out of loyalty to Pletcher, the five Castellano-Pletcher runners have finished sixth, sixth, 10th, 16th and 13th in the Derby. If you like Audible, I can see why, but I will be inclined to stand against on top.

6. Good Magic (Jose Ortiz/Chad Brown) -- 12-1Good Magic will try to join Street Sense and Nyquist as Breeders' Cup Juvenile champs who went on to win the Derby. His Fountain of Youth was terrible, but he bounced back in his second start of the year to win what I thought was a rather weak Blue Grass. His running style fits the profile of how I think the race will be won, but I have mixed feelings on him. It seems like he's a trendy upset pick, and you'll get nowhere near the 12-1 money line on him. I'll use him on my tickets as a backup, as I would hate to miss out on cashing because of him, but I'm not 100 percent sold.

7. Justify (Mike Smith/Bob Baffert) -- 3-1I don't think he could have drawn any more perfectly than he did. He has two dedicated front-runners to his left in Promises Fulfilled and Flameaway, along with three stone-cold closers to his outside in Lone Sailor, Hofburg and My Boy Jack. That should allow him to secure a great stalking spot into and around the first turn. I'm not a believer in the whole Curse of Apollo deal. Curlin didn't lose the Derby because he was unraced at 2 years old; he lost because he drew Post 2, and Street Sense ran huge. Bodemeister didn't lose in 2012 because he was unraced at 2 years old; he ran a winning race and got beat late by longshot I'll Have Another.Are there concerns? Of course. In his three starts, Justify has beaten 14 horses. He'll have to beat 19 on Saturday. Sure, he has just three lifetime starts, but so did Big Brown before he won the Derby from Post 20. He's looked great here in his workout. I'll never talk anyone out of trying to beat a favorite if they like a price horse, but if he does indeed get the trip I laid out above, he will be awfully hard to beat and leave out of the trifecta, making a sixth-straight Derby-winning favorite very likely.

8. Lone Sailor (James Graham/Tom Amoss) -- 50-1He couldn't get by Noble Indy in Louisiana, but that second-place finish got him an invite to the Derby. Lone Sailor ran well at Churchill Downs as a 2-year-old, finishing second in the Street Sense Stakes, before a bad post cost him any shot in the Kentucky Jockey Club Stakes. He can't win, but my hunch is the connections are here to get a thrill seeing him finish down the lane and pick off some tiring horses. I'll be using the closer underneath.

9. Hofburg (Irad Ortiz Jr/Bill Mott) -- 20-1He's the wise-guy horse of 2018, so if you think you're getting anywhere near 20-1, you're wrong. But he's still worth using in the exotic pools. Like Justify, he's only raced three times and could improve more here in his second start against winners. He'll be coming from out of it, so like many of those types, he may have to deal with traffic problems. But when Bill Mott sends one to the Derby (hasn't had a Derby runner since 2009), it's worth taking notice. I'd be surprised if he stepped up and won, but it wouldn't surprise me if he ran well and got a slice, especially with how well he has worked locally.

10. My Boy Jack (Kent Desormeaux/Keith Desormeaux) -- 30-1He's got the shortest layoff of any entrant, as he needed to win the Lexington Stakes to get into the Derby. He's reportedly gotten a little warm in his workouts leading up to the race, so who knows if that's a sign he might not be at his best on Saturday. I think he's absolutely worth using in the trifecta, as he, like many, will be passing tiring front-runners. He's got a decent kick, and My Boy Jack was beaten by Mendelssohn by just three lengths from a brutal post in the BC Juvenile Turf at 11-1. It's not like he hasn't been well backed or respected in previous races.

11. Bolt d'Oro (Victor Espinoza/Mick Ruis) -- 8-1Bolt d'Oro won at the San Felipe Stakes and had the misfortune of running into Justify at a huge pace disadvantage at the Santa Anita Derby. I'm not concerned about the jockey change -- it's not like Victor Espinoza and his three Kentucky Derby wins are a disadvantage. We know he can get the distance, as evidenced by his brutal trip as the odds-on favorite in the BC Juvenile. He has the right stalk/press profile for a potential winner. Could this be an Indian Charlie/Real Quiet or Empire Maker/Funny Cide situation in which one horse won the preps, but was then beaten on the first Saturday in May?If looking for a reason to knock him, his workouts haven't been the greatest, although he reportedly isn't the best workout horse. The battle with McKinzie first off the layoff and then chasing Justify around in the Santa Anita Derby could have taken too much out of him. Still, if you're looking to beat the favorite, this is the best place to start.

12. Enticed (Junior Alvarado/Kiaran McLaughlin) -- 30-1Enticed won over the track in the Jockey Club last November, and then was an easy winner in the Gotham. He ran OK in the Wood and was bumped repeatedly by the winner Vino Rosso, but was clearly second best. He's not on the list of contenders, but he also isn't among the longest shots out there. My guess is he goes around the track and finishes somewhere between ninth and 12th while never threatening.

13. Bravazo (Luis Contreras/D. Wayne Lukas) -- 50-1Bravazo broke maiden here, but I can't see him being much more than a nuisance on the lead. He was a fluke winner of the Risen Star in a race that hasn't proven to be very productive and was oddly run. Lukas has won Triple Crown races with some hard-to-figure longshots before, but I would be stunned if this was one of them. I'm totally tossing him.

14. Mendelssohn (Ryan Moore/Aidan O'Brien) -- 5-1Until one of the UAE Derby winners comes here and runs well in the Derby, I'm standing against them. Mendelssohn had everything his way in crushing a weak field in the UAE Derby, and he beat me in the BC Juvenile Turf when he was sent off as the 5-1 favorite one race after being 50-1. He'll probably be just behind the leaders, and then it's just a matter of how he handles dirt in his face. In an odd quirk, Post 14 hasn't produced a winner since 1961, the longest drought for any post which has produced a winner. In a field this size, you need to stand against someone. I'll use the past history of no UAE Derby winner finishing better than sixth as one of the reasons Mendelssohn will not be on my ticket.

15. Instilled Regard (Drayden Van Dyke/Jerry Hollendorfer) -- 50-1Instilled Regard drew into the field following a couple of injury defections. He had some good form as a 2-year-old and early as a 3-year-old, but hasn't really improved to be a legit contender here. Any horse who was able to run with McKinzie has some talent, and while I don't think he can contend for the win, I'll use him for third and fourth.

16. Magnum Moon (Luis Saez/Todd Pletcher) -- 6-1He seems to be getting very little respect leading up to the race with how he finished in the Arkansas Derby. Like Justify, Magnum Moon was unraced at 2 and is undefeated. He's one of three Pletcher trainees starting from the auxiliary gate and will have to avoid being wide around that first turn. Well-regarded Arkansas Derby winners typically hold their form and run well in Louisville, as the seven horses since 2004 that were a top-four betting choice combined to go 2-1-3 in the top three, with Classic Empire's fourth-place finish last year the worst of the bunch. This is Luis Saez's first real live mount in the Derby, so let's see how he handles it. My guess is he will be pretty aggressive, and it could cost Magnum Moon late. He can win, but I'm inclined to stand against.

17. Solomini (Flavien Prat/Bob Baffert) -- 30-1The "other" Baffert horse is a one-pace, consistent type who has been soundly beaten by a few of the other logical contenders in there. Jockey Flavien Prat typically gets his horses to finish well, and that will be to Solomini's advantage. Nobody has won from Post 17, and Solomini won't be the first, but he could be worth using for third and fourth. He's never ran a bad race, but he's also never ran a good enough race to win here.

18. Vino Rosso (John Velazquez/Todd Pletcher) -- 12-1He was the winner of the Wood Memorial, but that hasn't been a good thing lately in terms of Derby success. Since Fusaichi Pegasus won the Wood in 2000, 10 of 13 Wood winners ran in the Derby as a top-5 betting choice, and seven of the 13 sent off as a top-3 choice. Just two finished in the money: Empire Maker (second in 2003) and Congaree (third in 2001).I didn't like his races at Tampa at all, but despite the bumping with Enticed, his Wood was a lot better. Will the same jockey/trainer combo win two years in a row? Doubtful, but I'll still be using him in the exotics, as we know he can finish from off-the-pace and the price will be right.

19. Noble Indy (Florent Geroux/Todd Pletcher) -- 30-1I don't see any way he works out a trip from here. He's a speed horse from an outside post that has to go, and that makes him far more likely to finish last than first.

20. Combatant (Ricardo Santana/Steve Asmussen) -- 50-1I'll be using him underneath, as he reminds me a bit of Lookin at Lee (who finished second in the Derby last year) and Creator (who won the Belmont Stakes in 2016). He broke his maiden for fun here in his second lifetime start and can finish. He won't give Steve Asmussen his first Derby win in 19 tries, which is the most number of starts without a win in Derby history, but he will make a good account of himself from way out of it at a huge number.

Potential ways to play the race

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$0.50 trifecta7/2-5-6-8-9-10-11-14-16-17-18-20/2-8-10-11-20$25.00
$0.50 trifecta7/2-8-10-11-20/2-5-6-8-9-10-11-14-15-16-17-18-20$27.50
$0.50 trifecta5-6-11-18/7/2-5-6-8-9-10-11-14-15-16-17-18-20$22.00
$1.00 trifecta7/11/2-5-6-8-9-10-14-15-16-17-18-20$12.00
$1.00 trifecta11/7/2-5-6-8-9-10-14-15-16-17-18-20$12.00
$1.00 trifecta7/2-5-6-8-9-10-14-15-16-17-18-20/11$12.00
$1.00 trifecta11/2-5-6-8-9-10-14-15-16-17-18-20/7$12.00
$1.00 exacta box2-5-6-8-10-11-18$42.00
$1.00 exacta box5-6-7-10-11-18$30.00
$2.00 exacta7/2-5-6-8-10-11-18-20$14.00
$1.00 exacta2-5-6-8-10-11-18-20/7$7.00
$2.00 place-show2-8-10-20$16.00
$4.00 win-place-show11$12.00

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Other betting nuggets



  • Five straight, nine of the past 18 and seven of the past 11 Derby winners were the post-time favorite. From 1980-1999, favorites were 0-for-20. Five straight Derby winners have been single-digit odds. The last time there was a stretch of five straight Derby winners with single-digit odds was a run of nine years from 1971-79. Interestingly, since 2000, the average price of the winner has been nearly 13-1. That tells you if the favorite doesn't win, a real longshot could.
  • The third choice in the Derby wagering hasn't won the Derby since Strike the Gold in 1991.
  • Last year, Always Dreaming became the sixth straight horse to win the Kentucky Derby with a perfect record as a 3-year-old. This year, Magnum Moon (4-for-4), Audible (2-for-2), Mendelssohn (2-for-2) and Justify (3-for-3) are the only Derby contenders who are undefeated as 3-year-olds.
  • Justify will also be the 17th undefeated horse to be favored in the Derby. Seven of the 16 undefeated Derby favorites won. The only undefeated Derby winner not sent off as the favorite was Barbaro in 2006. The worst finish by an undefeated Derby favorite is ninth by Private Terms in 1988. The previous 16 have gone 16:7-3-2
  • This will be the seventh year in which Baffert sends the Derby favorite to post. He's won the race in just one of those previous six years. His one winner was an important one: American Pharoah went on to win the Triple Crown in 2015. In 1999, Excellent Meeting and General Challenge were part of a two-horse entry that was sent off as the favorite.
  • Baffert can win his 13th Triple Crown race with a win in the Derby. That would tie him with Sunny Jim Fitzsimmons for second all-time among trainers.
  • The five jockeys aboard the top five choices on the morning line -- Mike Smith, Ryan Moore, Luis Saez, Javier Castellano and Victor Espinoza -- are a combined 49:4-4-2 in the Kentucky Derby (four wins, four seconds and two thirds from 49 mounts). Smith and Espinoza are 32:4-4-2, while Moore, Castellano and Saez are 17: 0-0-0.
  • Mike Smith (Justify) has had 57 career Triple Crown mounts (23 in Kentucky Derby). This weekend, he will equal Eddie Arcaro's mark of 58 career Triple Crown mounts. Since winning the Derby in 2005 on Giacomo at 50-1, Smith hasn't had much success in the Derby, as he has just one top-3 finish in that span from 11 mounts (second on favorite Bodemeister in 2012). In his last four Derby mounts, Smith has finished 13th, 15th, 15th and 12th.
 

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