Looking for a difficult (but potentially lucrative) handicapping challenge? Then check out Friday’s $200,000 Remington Springboard Mile Stakes at Remington Park. You’ll be hard-pressed to find a more confusing stakes race anywhere in the country this week.

Held over a mile on dirt, the Springboard Mile serves as a Road to the Kentucky Derby Presented by Woodford Reserve prep race awarding 10 qualification points to the winner. Although it’s not a graded stakes race, the Springboard Mile has been rising steadily in prominence, producing five Kentucky Derby starters over the last decade.

Outadore (Coady Photography)

However, the 2020 Springboard Mile looks more like a steppingstone toward the 2021 Grade Belmont Derby on grass than the Kentucky Derby on dirt. After all, the two most accomplished runners in the field – morning line favorites #8 Cowan (4-1) and #9 Outadore (3-1) – have both done their best running on turf.

If you watched the 2020 Breeders’ Cup at Keeneland, then you’re already familiar with both colts. Outadore turned in a gutsy pacesetting effort to finish third in the Grade 1 Breeders’ Cup Juvenile Turf Presented by Coolmore America, while Cowan unleashed a big rally from off the pace to finish second in the Grade 2 Breeders’ Cup Juvenile Turf Sprint.

But although their talents are obvious, it’s difficult to predict how they’ll perform while transitioning to dirt for the Remington Springboard Mile. Outadore might be a son of Grade 1 Wood Memorial winner and Kentucky Derby starter Outwork, but so far he’s campaigned exclusively on grass. The Wesley Ward trainee won his first two starts sprinting and actually defeated Cowan in the Kentucky Downs Juvenile Turf Sprint prior to his Breeders’ Cup effort.

Perhaps Outadore will follow the example set by his sire and handle dirt just fine, but the surface switch isn’t the only question Outadore must answer. The way he weakened down the homestretch of the Breeders’ Cup Juvenile Turf hints that a mile might be pushing the limits of his stamina.

The distance question also faces Cowan. A son of talented sprinter Kantharos, whose progeny primarily excel over short distances, Cowan’s best races have come when sprinting less than three-quarters of a mile. When he’s tried to run a bit further, he’s faltered, most notably when fading to finish fifth in the Runhappy Juvenile Stakes on dirt – his longest race to date at seven-eighths of a mile, and also the only off-the-board finish of his career.

Of course, there are many reasons to respect Cowan’s chances. He’s the fastest horse in the field from a Brisnet Speed rating perspective, and he did win his debut over the dirt track at Churchill Downs. Furthermore, Cowan campaigns for hot connections – Hall of Fame trainer Steve Asmussen (a seven-time winner of the Springboard Mile) and jockey Stewart Elliott have teamed up to win at a solid 22% rate over the last two months.

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But since Cowan is questionable to handle the one-mile journey, why not favor the other Asmussen trainee, #7 Saffa’s Day (12-1)? He might not be as flashy at first glance, but there are reasons to believe the chestnut colt can outrun expectations.

For starters, Saffa’s Day was very impressive in his debut sprinting at Keeneland. Facing 10 rivals, Saffa’s Day dueled for the lead through fractions of :22.06 and :46.03, then powered clear to win by 5 ¼ lengths. The 90 Brisnet Speed rating he posted isn’t far off the best figures earned by Cowan and Outadore.

Saffa’s Day did regress when stepping up in class for Nyquist Stakes at Keeneland, but wheeling back on relatively short rest and chasing fast fractions of :21.73 and :44.65 may have compromised his chances. Keep in mind, the Nyquist field was deep – runaway winner Highly Motivated set a track record and is an early favorite for the Kentucky Derby, while fifth-place finisher Sir Wellington returned to win the Louisiana Champions Day Juvenile Stakes last week.

As a son of Grade 1 Blue Grass Stakes winner Carpe Diem, Saffa’s Day is bred to handle at least a mile, so there’s a chance he’ll shown improvement while stretching out in distance. He’s also slated to race with Lasix for the first time on Friday, a subtle shift that could boost his chances.

The only downside to supporting Saffa’s Day is the fact there’s a lot of speed in the Remington Springboard Mile field, which could set up a destructive pace duel favorable to late runners. In this instance, #1 Senor Buscador (15-1) would warrant respect as a live longshot.

A son of 2003 Horse of the Year Mineshaft (who tends to pass stamina on to his foals), Senor Buscador was an eye-catching debut winner at Remington Park last month, rallying from ten lengths behind to crush his rivals by 2 ½ lengths. Third-place finisher #11 Flash of Mischief (15-1) returned to win his next start and is likewise entered in the Springboard Mile.

As one of the local runners in a field full of classy out-of-state shippers, Senor Buscador is bound to be overlooked in the betting, but his stretch kick could make him dangerous at a fair price. Trainer Todd Fincher wins at solid 22% rate with horses running long for the first time, so there’s no reason to think Senor Buscador won’t be ready to handle the added distance of the Springboard Mile. If a hot pace ensures, he can be involved at the finish.

Let’s employ a bold wagering strategy, favoring Saffa’s Day and Senor Buscador on top of an exacta while excluding Outadore and Cowan from the top spot. We will use the favorites underneath, but we won’t rely on them entirely – we’ll also throw in #10 Joe Frazier (5-1), who ships in off a third-place effort in a 1 1/16-mile allowance race at Churchill Downs. If one of our longshots comes home on top, we’ll be set for a solid payday.

Wagering Strategy on a $24 Budget

$4 to win on #1 Senor Buscador

What to say at the betting window: Remington Park, 12th race, $4 to win on 1

$4 to win on #7 Saffa’s Day

What to say at the betting window: Remington Park, 12th race, $4 to win on 7

$2 exacta: 1,7 with 1,7,8,9,10 ($16)

What to say at the betting window: Remington Park, 12th race, $2 exacta: 1,7 with 1,7,8,9,10

Good luck, and enjoy the race!