Monday’s Shoemaker Miles Stakes at Santa Anita Park is a great race for a number of reasons. For starters, the Shoemaker Mile is a Breeders’ Cup Challenge Series “Win and You’re In” race that offers the winner a guaranteed spot in the 2020 Breeders’ Cup Mile at Keeneland.

Watch the Shoemaker Mile on Monday, May 25 from 6-8 p.m. ET on NBCSN, NBCSports.com and the NBC Sports app.

The race also features last year’s Preakness Stakes winner, War of Will, making his season debut. Despite his triumphs on the dirt in 2019, War of Will started his career on the turf and his pedigree suggests that he’s very likely to be just as successful on the grass. That said, the Shoemaker Mile will be his first start off of a six-month break, and I’m going to try to take a swing or two with some horses who could upset the apple cart at longer odds.

Let’s start out with the horse on the rail, Without Parole. He won the Group 1 St. James’s Palace Stakes going a mile at Ascot back in 2018. His three other career wins have all came at this mile distance as well. Granted, he hasn’t won in six races since the St. James’s Palace but he did finish a fast-closing third two starts ago in a much tougher U.S. debut in the TVG Breeders’ Cup Mile. Irad Ortiz Jr. rode Without Parole in that race and he will reclaim the mount on him again on Monday.

Without Parole has only had one race this year and it was in the Pegasus World Cup Turf Invitational in which he finished second to last. However, he had several excuses right from the start of that race when he got squeezed coming out of the gate. He also raced in traffic throughout and got cut off several times in the stretch before Frankie Dettori — who had come from Europe to ride him at Gulfstream — finally just wrapped up on him. The Pegasus World Cup Turf also was a race that didn’t allow him to run on Lasix (furosemide) after he’d shown significant improvement racing on Lasix for the first time at the Breeders’ Cup.

Stream the 2020 Shoemaker Mile live here

How much of a factor might Lasix be for some horses? Well, let’s next look at the horse who finished last in the Pegasus World Cup Turf: Next Shares. In his following start (back on Lasix) in the Grade 1 Frank E. Kilroe Mile Stakes, Next Shares finished third (beaten just a neck) to River Boyne. Both Next Shares and River Boyne return in the Shoemaker Mile and I prefer the former as a pace play who has plenty of back-class. If you rewatch the Kilroe Mile, Next Shares covered a lot more ground than River Boyne. With a similar effort, Next Shares could certainly turn the tables.

The other thing to like about Next Shares is that his trainer, Richard Baltas, has entered speedster Neptune’s Storm in the Shoemaker Mile. That horse, along with Voodoo Song, should ensure a very brisk pace up front — they’ll also be kept honest by Blitzkrieg and War of Will, both of whom usually race on or near the lead. All of that speed adds up to good news for Next Shares. He’s a Grade 1 winner who has always done his best running when he’s had some pace to run into. The other two keys for him (like all stalking or closing-type runners) is clear running room late, and hopefully he’ll get that with Hall of Fame rider John Velazquez taking the mount.

Lastly, we should take a look at True Valour. It’s hard to make much of an excuse for his flat finish in the Kilroe last out, but he’s truly performed better than what his results on paper might indicate. In the Thunder Road Stakes in February, he looked pretty keen early and it took him a few strides to settle down without throwing his head around and fighting his rider. Turning for home, it was clear that jockey Andrea Atzeni had plenty of horse under him but was just waiting for some running room. It ended up coming too late because River Boyne was in a better spot and had already taken command. True Valour did split horses nicely in the closing stages and was half a jump away from finishing second.

If you go back to the Breeders’ Cup Mile, True Valour had excuses there, too. He was up on heels early and he again took a little bit of time to settle down into a comfortable stride. Then, turning for him, he was just waiting for running room but instead got stuck behind a wall of horses. True Valour ended up steadying pretty badly and lost all chance at that point. I’m a little worried about how headstrong he tends to be early in races, but there’s a scenario here that could have at least two horses battling for the lead early and opening up some daylight on the rest of the field. That means he’ll be less likely to be running up on anyone’s heels and it also ensures that he’ll have a nice setup. Whether he can navigate clear passage late in the race is a separate matter.

Longshot Selections

#1 Without Parole

#3 Next Shares

#2 True Valour

Watch the Shoemaker Mile on Monday, May 25 from 6-8 p.m. ET on NBCSN, NBCSports.com and the NBC Sports app.

Betting an exacta can present a challenge on several levels.

There is, of course, the primary need to analyze past performances and decide which horses are going to finish first and second.

Yet because of the inherently lower payoffs as opposed to what you’ll find in a Pick 3 or Pick 4, you’ll need to structure your wagers effectively in order to turn your selections into a profitable wager.

For starters, an exacta can be a simple wager. If you like two horses equally, you can just box them in the exacta and collect so long as they finish 1-2 in any order. If you like one of them a little more, you can then bet more on the one you prefer, say $10 on a 1-2 exacta and $5 on 2-1.

If you’re a little more uncertain, make sure you structure your bet around the size of the field and the probable payoffs.

If you like a longshot, the higher probable payoffs give you the cushion you need to wager on more combinations and still turn a nice profit.

But if you’re dealing with favorites or horses at relatively low odds, you have to wager more efficiently to preserve your profit.

In a field of six or less, you’re best to either focus on one horse or box two of them instead of boxing three or more horses because of the small payouts the bet will most likely generate.

In a field of seven, a wise strategy would be to box your top two choices and then, if you are worried about other horses, play them top and/or bottom other the other horses. For example, box 1-2, then bet 1-2 over 3-4 and 3-4 over 1-2. This way you are getting coverage on four horses without having to box them.

Once you get an eight-horse field, as long as there is not an overwhelming favorite, you can expand the number of horses you box since the payoffs will typically be higher, giving you a better opportunity to offset the inevitable array of losing tickets in a boxed wager.

The biggest race in North America on the first Saturday in May this year isn’t the Kentucky Derby Presented by Woodford Reserve, which has been moved to the Sept. 5, the first Saturday of that month.

Instead, we have a very good pair of big races in the form of split divisions of the Grade 1 Arkansas Derby at Oaklawn Park, which occurred after 22 horses were entered to run in the race (two have since scratched, one from east division). Each division offers a $500,000 purse and 100 points to the winner via the Road to the Kentucky Derby qualifying series, with 40 to the runner-up, 20 to the third-place finisher and 20 to the fourth-place finisher. Watch the Arkansas Derby on NBCSN, NBCSports.com and the NBC Sports app on Saturday, May 2 from 6-8 p.m. ET.

Leading the first division of the Arkansas Derby is Charlatan, who is undefeated and untested in two races to date. Both wins were earned leading from start to finish and this colt should have an easy lead once again in this race as there aren’t any other horses likely to take him on in the early stages for fear of costing themselves a chance at success, or at least some Kentucky Derby points. Charlatan earned a career-best 108 Equibase Speed Figure winning his most recent race, which is the best figure earned by any horse in the field, and he could improve off the effort in his third career start. However, Charlatan is stretching out to a mile and an eighth distance as well as running in a stakes race for the first time, while others have experience at the distance and/or at this level.

Anneau d’Or is one of those horses as he was the runner-up by a head in the Grade 1 TVG Breeders’ Cup Juvenile last November, earning a 106 Equibase Speed Figure. He subsequently finished second by a neck one month later in the Grade 2 Los Alamitos Futurity to prove his Breeders’ Cup effort was no fluke, and then took two months off and finished ninth in the second division of the Grade 2 Risen Star Stakes Presented by Lamarque Ford on Feb. 15 when he tried blinkers for the first time. With that equipment removed for Arkansas Derby, it’s very possible Anneau d’Or can return to his form of last fall, and if he does that might be good enough to win this race. One more thing Anneau d’Or may have going for him is his pedigree for this distance – his sire is Medaglia d’Oro, and he is out of a Tapit mare. Per a STATS Race Lens pedigree query, sons and daughters of Medaglia d’Oro have the most wins in dirt route stakes races at distances of 1 1/8 and 1 1/4 miles compared with any other sire who has entrants in the Arkansas Derby field.

Gouverneur Morris is proven at the level based on his runner-up effort in the Grade 1 Claiborne Breeders’ Futurity last October. After skipping the Breeders’ Cup Juvenile in November to prepare for his 3-year-old campaign, Gouverneur Morris returned to win at a mile and 40 yards in February. One month later in the Grade 1 Curlin Florida Derby, Gouverneur Morris finished fourth of nine and boosted his top Equibase Speed Figure to 104. Although Constitution, the sire of Gouverneur Morris, has not had many horses run to date, one of those is the undisputed leader of the division That horse, Tiz the Law, won the Florida Derby impressively. Gouverneur Morris is making his third start off a layoff and is on a pattern for an even better effort, which could be good enough to win this division of the Arkansas Derby.

Win Contenders:

Anneau d’Or

Charlatan

Gouverneur Morris

The rest of the field, with their best Equibase Speed Figures, is: Basin (96); Crypto Cash (93); Jungle Runner (85); Mo Mosa (92); My Friends Beer (89); Winning Impression (89); and Wrecking Crew (100).