First, the unpleasant tidbit that you may have already heard: I’m out of a job.

Back in November, I was hired by MOAC, a blockchain company based in Silicon Valley. This came two months after my job at The Daily Racing Form was transitioned from full-time to part-time. Unfortunately, earlier this week, I was informed that the company had dissolved its marketing team. As such, for the second time in six months, I’m actively searching for work.

Please let me stress that this isn’t a funeral or a pity party. Due in large part to the best support system anyone could ever hope to have, I’m confident I’ll land on my feet. However, if you happen to be out there looking for a horse racing, content creation, social/digital media, and/or marketing professional, I’d love to chat with you. You can reach out either via Twitter or this site’s “contact” feature.

Regardless of external circumstances, writers will always write, and semi-professional horseplayers will always give opinions about playing horses in a semi-professional manner. That’s why I’m here. We’ve got three Kentucky Derby preps coming up this weekend, and I’ll also be dissecting the associated Pick Four sequences.

There’s a lot to go through, so let’s get to it!

AQUEDUCT

Kentucky Derby Prep: Gotham S. (G3), Race 10
Late Pick Four: Races 8-11

We’ll start off at The Big A, which features, for my money, the strongest renewal of the Gotham Stakes in many years. It anchors a terrific all-stakes Pick Four, and it features one of the most talked-about 3-year-olds in the country.

That’s #6 INSTAGRAND, who ships cross-country for Hall of Famer Jerry Hollendorfer. How good was he as a 2-year-old? Based on Beyer Speed Figures, he likely doesn’t have to improve at all to beat this solid group, and any sort of improvement would make the even-money morning line look like a real overlay. He’s worked well of late, and while the added distance is always a question mark, his breeding suggests a one-turn mile will not be a problem.

As a handicapper, I want to find a reason to go against him, but I can’t. Simply put, I think he’s much more talented than the group lining up against him. There’s a lot of speed signed on, to be sure, but I don’t think he needs the lead in order to win. I think he’ll likely sit off the speed and be in prime position going into the turn. With that sort of trip, I don’t think he loses.

If you insist on trying to beat the chalk, the most intriguing alternative strikes me as #5 HAIKAL, who may be the race’s true lone closer. He hasn’t run particularly fast, but based on the pace scenario, he’ll likely have much more left in the tank late than most of the opposition. The faster they go early, the better he’ll like it, and because of that, the play may be a Dave Weaver-style “ice cold exacta” using Instagrand on top of this 6-1 shot.

$0.50 Pick Four: Race #8

R8: ALL
R9: 2,7,8
R10: 6
R11: 3,7,12

63 Bets, $31.50

While Instagrand figures to be very tough to beat, I do think there’s value in the late Pick Four. I’ll try to get a price or two home along with my Gotham single to make this pay a bit.

We’ll be guaranteed to get to the second leg, as I’m buying the Grade 3 Tom Fool. I thought this was a confounding race with a foggy pace scenario and a vulnerable favorite. #3 SKYLER’S SCRAMJET ran well twice here earlier in the meet, but hasn’t won since this race last year and may not be the same horse. With a fairly short field of seven, buying this race doesn’t result in an overpriced ticket.

The ninth is the Stymie Stakes for older horses, and it’s drawn a fun field for the level. #2 SUNNY RIDGE can certainly win, as can the returning #8 VINO ROSSO, but I’m pretty intrigued by a price. That’s #7 SHIVERMETIMBERS, who has run in some tough races out west. A scan of his running lines reveals an abundance of graded stakes-caliber horses, and all three of his wins have come at this one-mile distance. I doubt we’ll get his morning line price of 12-1, but if he wins, it’s likely that a lot of Pick Four tickets get knocked out.

We’ll hope to be alive to three horses in the finale, the Busher Stakes for 3-year-old fillies. I’m taking a bit of a shot here, as I don’t like favorite #10 PLEASE FLATTER ME or second choice #11 ALWAYS SHOPPING. The former gets a huge class and distance test and likely won’t be alone in wanting the lead, while the latter is likely better going two turns and wants much further than this one-mile distance. Of the two Todd Pletcher trainees, I prefer #12 ORRA MOOR, who has been impressive in back-to-back wins at Gulfstream Park. I’ll also use #3 OXY LADY, who won at this route back in November, and #7 FILLY JOEL, who cuts back to one turn after showing two turns may be a bit further than she wants to go.

TAMPA BAY DOWNS

Kentucky Derby Prep: Tampa Bay Derby (G2), Race 11
Late Pick Four: Races 9-12

The Tampa Bay Derby serves as the main event on a terrific card. The race drew a field of 11, and I think it’s a great betting race because I don’t like the morning line favorite.

I acknowledge that #7 WIN WIN WIN was very impressive in winning the Pasco Stakes. However, that race fell apart, and I don’t think he beat much. He’s never been two turns, and at his likely short price, I’m going to try to beat him.

#4 DREAM MAKER, like most offspring of Tapit, likely needed some time to grow up. Judging by his smashing win last month at Fair Grounds, he’s come a long way from two duds in stakes company last year. If he builds off of that last-out effort, I think he’s the one to beat, and we may get a bit of a price given the large field signed on.

The early pace is going to be interesting. If #5 WELL DEFINED gets an easy lead, he’ll likely be tough to catch. His win in the Grade 3 Sam F. Davis here was very good, and a repeat effort puts him right there. My slight hesitation here is due to the presence of #11 ZENDEN, who may be sent hard from the gate and could present some pace pressure. However, I need to have Well Defined on my tickets, just in case Zenden either doesn’t clear from his outside post or is rated in his first two-turn effort.

$0.50 Pick Four: Race #9

R9: 2,7
R10: 1,3,4,5,10
R11: 4,5
R12: 5,10

40 Bets, $20

Unfortunately, I don’t think there’s much room for huge prices in this sequence, so I made an effort to keep the cost of my ticket down. Still, the field sizes involve hint that we could get a surprising return on investment if we cash.

The ninth is the Grade 2 Hillsborough for older distaffers on turf. I’m using the two likely favorites in #2 HAWKSMOOR and #7 RYMSKA. I do prefer the latter, as Hawksmoor may want a touch shorter than this nine-furlong distance, but these two certainly seem to be the class of this group.

The best betting race of the sequence is probably the second leg. It’s the Grade 3 Florida Oaks for 3-year-old fillies, and I had to spread. #5 CONCRETE ROSE and #10 STELLAR AGENT both have talent, but they’re also making their 2019 debuts. I’m most intrigued by #3 WINTER SUNSET, who’s bred to be a really nice filly and is 2-for-2 coming into her graded stakes debut.

After the Tampa Bay Derby, the finale is a $25,000 claimer on the grass. Likely favorite #5 TRUMPI’s record looks significantly better if you toss the races at Gulfstream Park, which boasts a surface that simply may not agree with him. He adds blinkers in his first start for Dale Bennett, and he seems like the horse to beat. I’ll also use #10 SIMMARDSTRIKE, who drops in for a tag and may relish the cutback from nine furlongs to a mile. The outside post is a problem, but he could be rolling late at a fair price.

TURFWAY PARK

Kentucky Derby Prep: Jeff Ruby Steaks (G3), Race 11
Late Pick Four: Races 9-12

It’s never easy to predict which horses will like a synthetic track, which makes the Jeff Ruby an incredibly tricky affair to handicap. The likely favorite is #10 SOMELIKEITHOTBROWN, who first came onto the scene winning a race at the wrong distance at Saratoga (never forget) and has since won the local prep for this race, the Battaglia.

He’s certainly good enough to win, and I need him on my tickets. However, there’s another I need to use, and it’s one of those “first-time synthetic” horses. That’s #3 FIVE STAR GENERAL, who figures to be the main speed in this race. He didn’t break well in the Sam F. Davis, but won two off-the-turf races in a row before that, including a stakes race at Aqueduct. They’ve clearly wanted to get on turf for a while, and that’s often a sign that a horse will like a synthetic track. Somelikeithotbrown may be better, but I need to use Five Star General in case he gets brave on the front end.

$0.50 Pick Four: Race #9

R9: 1,8
R10: 3,5,6,11
R11: 3,10
R12: 1,6,7,10

64 Bets, $32

The Jeff Ruby is one of three stakes races in this sequence, which seems to present some value given the big fields and lack of heavy favorites (save for Somelikeithotbrown). Hopefully, my $32 ticket provides enough coverage.

We’ll start off with the Kentucky Cup Classic for older horses, and I’m using the bookends. #1 NUN THE LESS makes lots of sense given his two-back win over similar foes, and he’ll likely go favored, but my top selection is actually #8 LANIER, who seems like the race’s lone speed. He wants to go longer than he ran last time out, and I think he could get very comfortable on the front end. He was just a length behind Nun the Less two back, and that was with a respectable pace. If they go slower (and I think they will), this one could wire them at a fair price.

The second leg is the Bourbonette Oaks, and like the Jeff Ruby, it’s attracted several out-of-town shippers. My top pick is #5 INTO TROUBLE, whose lone start on a synthetic surface was a last-to-first score at Arlington in September. However, I do think there’s room for a price. #3 BIRDIE was very impressive last time out at this route, while #6 RED ROUNDER’s last race at Fair Grounds seems like a throw-out. Finally, #11 DIVA DAY is bred up and down for this trip and could improve off of a debut win at a big price for a top local barn.

We’ll hope to be alive to four horses to finish this off. #7 BYE BYE BULLY’S may be favored, but I don’t think she’ll be her 8/5 price given the large field. 5/2 or so seems much more likely, and while she could easily win, I can’t simply rely on her alone in the payoff leg. #1 GOLDEN LOCH had a wide trip when second at this route last time out, and second-time starters #6 LYNDA D and #10 SAILOR’S CAP could easily step forward here at big prices.