2019 Kentucky Derby Staff Favorite Betting Picks: A True Smorgasbord of Bets

It's the first Saturday in May, which means it's time for sports bettors everywhere to shift their attention to Louisville for the Kentucky Derby. Whether you are a horse expert or betting for fun, there is plenty of action to go around while you sip on a mint julep (or just stick with the bourbon neat … more on that later).

I decided to poll our staff for their favorite 2019 Kentucky Derby bets, knowing that some would have serious takes while others will simply find a name that suits them best (or literally throw a dart … more on that later as well).

I ended up getting bets from 23 members of our staff — and got a little bit of everything. You will find plenty of bets to win but also some matchups and bets to place/show among other wagers. Sit back and get ready to at least laugh at some of the stories while you possibly find the horse you want to back during "the most exciting two minutes in sports."

Our Staff's Favorite Kentucky Derby Bets

Evan Abrams: Spinoff (-135) over Long Range Toddy

Spinoff has more potential to finish top-5 and stay close to the pack. Long Range Toddy, who is coming off a run in the Arkansas Derby, has struggled in bad weather recently and is trained by Steve Asmussen, who is famously 0-of-19 at the Derby. I think Spinoff has a much better shot at the top.

I also like two top-5 finish props:

• Win Win Win (+290)
• Master Fencer (+700)

With the auxiliary gate at the Kentucky Derby holding a special place among the triple crown races, certain jockeys tend to prefer the outside of the main gate (post 14) or the inside of the auxiliary gate (post 15), mostly for the extra space the horse receives coming out of the gate.

The data backs it up: in six of the past eight years, at least one of horses in the 14th or 15th post finished in the top five, including each of the past four years.

BlackJack Fletcher: By My Standards to Show (4-1)

By My Standards is going off on the morning line at 20-1, and while I expect that to drop to around 15-1 or so by post time, there is still incredible value here. This horse is peaking at the right time.

After struggling as a two-year-old, he has improved in each race as a three-year-old, culminating in a win at the Louisiana Derby. If his progression continues, he could be a great bet to hit the board on Saturday at a nice price.

Sean Zerillo: Code of Honor to Show (5-1)

Ultimately, I don’t think that Code of Honor will win the 2019 Kentucky Derby. Game Winner and Tacitus seem to me to be the most likely winners, and I’ll be using each in the top spot on my exotic tickets.

However, Code of Honor has been excellent in training during the lead up to the Kentucky Derby, running his final four furlong work in 46.8 seconds; the second fastest of 76 horses that day. His trainer, Shug McGaughey, has confidently stated that Code of Honor is ahead of where McGaughey’s 2013 Kentucky Derby Winner, Orb, was at this point in training.

Code of Honor is a midpack runner who needs pace in front of him before he makes his one late run. He got that pace in his victory in the Fountain of Youth, but didn’t in the Florida Derby as he finished third behind Maximum Security and Bodexpress.

Code of Honor came home strong in that Florida Derby, running 12.5 seconds in the final ⅛ of a mile, and 36.7 seconds over the final three furlongs. He simply spotted the leaders too much cushion.

Maximum Security should be chased by speed to his inside, like Vekoma and War of Will, early in this race, setting up an average to fast pace for Code of Honor and other midpack runners or closers to pick up some pieces.

Horses who win the Kentucky Derby are typically forwardly placed, but there’s plenty of room for midpack runners and closers to sneak into the exotics with an honest pace.

I think it would be a big mistake to leave Code of Honor out of your exactas, trifectas, and superfectas. I’ll be betting him to place (+775) and to show (+475), and building most of my exotic tickets around him too.

Steve Petrella: War of Will to Lead at Quarter Pole (5-1)

As a lazy millennial with a comically-poor attention span, I cannot be bothered to possibly sweat out this whole race. It’s just too long. That’s why I’m taking War of Will to lead at the quarter pole.

Why War of Will? He’s got early speed and drew the dreaded No. 1 post. It’s probably just posturing, but trainer Mark Casse literally said he’s going to send his horse to the front because if he doesn’t, he’ll get trapped inside and never have a chance.

So he’s praying War of Will gets out to a lead and all the other horses forget how to run, or run backward, or just go home. But we only care about the first 23-25 seconds or so.

If War of Will does get trapped inside, I’ll know the result of this bet in about 1.5 seconds, if that.

Chad Millman: Game Winner (5-1)

What I know about horse racing could fit onto a horseshoe.

I do love the way regulars at the track describe a “wall of sound” as the horses reach the finish-line, and the way wiseguys whisper about the horses on Wednesday, after they’ve seen them run the track. But I do know that, at 6:15 on Wednesday night, when Omaha Beach was scratched, the gasps in our office were as dramatic as if an actual disaster were happening. Clearly a lot of people love this race.

So here’s my take: The winning horse will be trained by Bob Baffert. He seems to be someone who knows what he’s doing. I'll roll with Game Winner.

John Ewing: Game Winner (5-1)

The Kentucky Derby betting favorite isn't a sexy pick. The colt lost its past two races and wasn't the favorite until Omaha Beach was scratched.

Nonetheless, the market has deemed the 2019 Eclipse Juvenile Champion as the most likely horse to win the Derby. The favorite has won the past six “Runs for the Roses” and this is no fluke after a new points system was introduced to determine the Kentucky Derby field.

Some consider this race wide open, but the odds and the history of Derby favorites suggest Game Winner will emerge as the champion.

Ian Hartitz: Game Winner (5-1)

Some people forget Ohio State beat Michigan 62-39 this past November. The Buckeyes were the “winner” of “The Game”, so this one is a no-brainer for me. Also, go Blue Jackets.

Josh "Action" Applebaum: Game Winner (5-1)

DISCLAIMER: I know nothing about horse racing. But I want the action. I NEED the action. Here’s what I’m thinking: every year I get mesmerized by a big payout and back a longshot because I want to be the wiseguy who cashed a 25-1 ticket. And every year I lose. So this year I’m taking a different approach.

Favorites have dominated in recent years. So who’s the new favorite? Game Winner. He’s a Bob Baffert horse. And Baffert is the Brady/Belichick of pony racing. Baffert recently said of Game Winner: “He is a champion. He’s always right there and has never run a bad race.” Sounds good to me.

Dan McGuire: Improbable (6-1)

There’s not much technical analysis here. I'm simply tailing the No. 5 horse. It’s been my go-to since I was a little kid at Red Sox Spring Training in Florida when Nomar Garciaparra walked up to me and handed me his bat with the number 5 on the knob. Luckily, the five-horse has won the Kentucky Derby four times since 2002 and ten times overall, the most for any post position.

It also doesn’t hurt that Improbable is one of Bob Baffert’s horses, runs well in the mud and obviously has a legitimate chance (~16%) to win the race.

It should be noted that because of two scratched horses, Improbable will actually run out of the sixth post, but for betting purposes it stays on five. Gray Magician will be in the fifth gate for the race at 50-1 odds so why not throw $5 on that, too.

Mark Gallant: Improbable (6-1)

Win Win Win? More like Lose Lose Lose. Game Winner? More like Game Loser. Maximum Security? More like Minimum Security.

Improbable? By definition, every single horse in the field is improbable. Not one of them even has a 25% chance of winning. At 6-1, Improbable may technically be living up to his name, but “Baby Justify” has a heck of a shot at taking this home in my book.

I used to cause mischief at a horse barn on the other side of the woods near my house, so if there’s one thing I know, it’s horses.

This baby loves the slop. Loves it. Eats it up. Eats the slop. Born to slop. His father was a mudder. His mother was a mudder.

He nearly beat Omaha Beach (RIP) at the sloppy Arkansas Derby. Since Omaha Beach swallowed his tongue or whatever, I reckon this is Improbable’s time to get probable. PLD also said that he’ll be running without blinkers this race after getting a bit fractious (horse lingo) in the gates in Arkansas. I personally bet the barn at 6-1 and advise you to do the same.

Vik Chokshi: Improbable (6-1)

First, let’s start with the gate number. Improbable will run from the sixth post, which is an advantage with his running style for a few reasons.

1. With rain in the forecast and a muddy track expected, the horses in the middle and the inside usually have an advantage.
2. Improbable has also run well in the slop before, with a second-place finish on a muddy track at the Arkansas Derby.
3. And, to top it all off, his mom and dad were both really good slop horses, with past success in the mud.

He is also a Bob Baffert horse. Baffert has won five Kentucky Derbys, the Triple Crown twice, and is arguably the greatest thoroughbred trainer of all-time. Love him or hate him, Baffert knows what he's doing.

Lastly, the horse’s age is also important. Historically, it has helped to be on an older three-year-old colt. Since 2013, all six Derby winners had a February or March foal date. Improbable’s foal date? February.

At 6-1, I like Improbable’s pedigree, slop experience, and post number coming into this race. Let’s go!

Danny Donahue: Roadster (7-1)

I threw a dart at a board and said I'd bet on whatever number I hit. But I missed the board hit bullseye. So, instead, I just decided to go with Roadster because I don't see how a car loses to a bunch of horses.

Sean Koerner: Tacitus to Win (8-1)

Starting from the age of 1-2 years old, my father would bring me to two of the parties he and his friends would throw every year:

1. Kentucky Derby party
2. Fantasy Football draft party

By the age of 7, I was obsessed with fantasy football. And by the age of 9 or 10, they let me actually draft a team. Then by the age of 12 or 13, my father considered banning me from the league. Who knows how much different my life would have been if I gravitated to horse racing instead …

Having said that, the Kentucky Derby is maybe the one betting event all year where I completely wing it. Pari-mutuel betting gives me anxiety because it’s essential I know I’m locking in a good price. Otherwise — what is the point? That’s why I have already locked in Tacitus at 8/1 as it looks like the odds for him are dropping at places.

He drew a great post position at No. 8 as the sweet spot seems to be anywhere from 5 to 10 for the Derby, and I also think Hall of Fame trainer William Mott finally gets his first Derby title with this horse. I also love rooting for gray horses so Tacitus checks that box for me as well. Sign me up!

Ken Barkley: Spinoff to Show (9-1)

I don’t think this horse can win the race. I actually don't think there are many horses who can win the race. The problem is the likeliest winners are being bet like it (Game Winner, Maximum Security, Roadster).

What I try to look for is a horse that people aren’t very excited about to hit the board and get a big piece, one that pays via exacta/trifecta or place/show wagers at an insane rate. The pools are so huge on Derby Day that if you are even remotely contrarian, the payouts are much larger than on a normal race day if you are correct.

A lot of people like By My Standards as this year's “surprise” horse, but I'm going contrarian with Spinoff, who only has four starts, and actually finished second to By My Standards in the Louisiana Derby. His pedigree, distance progression and myriad of excuses in that Louisiana Derby race (bumped at break, wide the whole way, By My Standards had ideal trip) make him completely overlooked heading into this race. He could be primed for his best performance yet.

The scratches also allowed him to move down stalls, which only helps. I’ll be including Spinoff with some of the big contenders in exacta/trifecta wagering and he could be the horse no one saw coming who hits the board a little further down.

Rob Perez: By My Standards (14-1)

In his previous races, Game Winner has been wide on final turns enough for me to consider it a legitimate concern/not a fluke or outlier. If this happens again with all of the horses running at the Kentucky Derby, he'll undoubtedly get left in the dust like Johnny Tran did to Jesse in Fast and the Furious. Don’t care how fast he is or what type of closing speed he has.

I am going to bet it happens again because:

1. He naturally does it.
2. Someone hugging the rail will force him out there unless he has a full-length lead coming to the stretch.

Roadster would be next in line but I don’t trust him at this distance as his recent wins were at half length.

Thus, I am on By My Standards — without a doubt the most underrated name in the field. He started off winless for some time, but caught the eye of every notable expert I trust in this field as he trained in the backyard of Churchill Downs. Then: victory at The Louisiana Derby. That right there was enough for me.

I’m buying low while I still can for the victory and coming in bigger on him to Show (+400) as the pool is going to be huge without Omaha Beach.

Collin Wilson: Win Win Win (15-1)

Win Win Win is obviously a Michael Scott reference. There may be no greater Office episode than ‘Conflict Resolution’.

Chris Raybon: Win Win Win to Win (15-1)

Life is too short to be turning down three-somes..

Jason Sobel: Code of Honor (17-1)

Man, I need to be a horse owner. All these thoroughbreds in the Kentucky Derby — and not a single one with a decent golf-related name?!

Then again, real horses with real golf names have had, well, pretty shitty golf names, including Birdie, Tee Off and the ever-creative Golf Ball. I mean, give me a Putting for Bogey. Or a Noonan. Or even a name that covers a rain-induced pet peeve for athletes in both of these sports: Mud Balls (they don’t go as far in golf and I can’t imagine it helps ‘em go any faster in horse racing).

Anyway, I’ll reluctantly take Code of Honor, which at least sounds like one of those green-binder golf books that calls the game an ethereal journey through a mystical kingdom or some corny garbage like that.

Stuckey: Tax to Win (22-1)

I bet Tax for two reasons:

1. My "horse guy" I trust told me to.
2. Nobody else here has said him.

I'm really just here so I don't get fined. Go Canes.

Daniel Scotti: Spinoff to Win (33-1)

A few weeks back when I checked odds, Spinoff was going off at 35-1, which caught my eye. In an old Bukowski poem titled “a 340 dollar horse and a hundred dollar [dirty word],” Hank bets a horse at 35-1 who ended up winning “like he was mad as hell” (cue Howard Beale in Network voice).

I’m hoping for a similar thing here. And that’s the extent of my track analysis.

Michael Leboff: Plus Que Parfait to Win (66-1)

I used to work in a gambler's bar. Whether it was quick draw, joker poker, real poker, sports or the ponies, someone was always gambling on something.

This type of establishment attracted more than a few Railbirds, one of whom was the late, great Taxi Wally. He used to say, you handicap the race, not the horse. I don't know if that's a common track-idiom or just Taxi Wally being Taxi Wally, but it makes sense for this edition of the Kentucky Derby.

If you've been following along with our horse racing coverage, you know that this race is wide open and, with Omaha Beach scratched and rain in the forecast, it will be unpredictable.

My strategy for handicapping the race is to zero in on a horse that has a big price and a puncher's chance in sloppy conditions. Plus Que Parfait ticks both of those boxes.

Matt Mitchell: Plus Que Parfait to Win (66- 1)

On the morning of the 2009 Kentucky Derby, I found myself inside the fabulous El Cortez casino in downtown Las Vegas. I’d lost boatloads of money the previous night, and awoke to find $20 remaining in my wallet. Feeling like I had nothing to lose, I went to the sportsbook to bet a longshot. I glanced at the Derby odds and had the following exchange with the ticket writer.

Me: “Kentucky Derby, $20 on 8 to win.”
Ticket Writer: “Alright, $20 on Mine That Bird to win.”
Me: “That’s the horse’s name?”
Ticket Writer: “Yep.”
Me: “That’s the stupidest name I’ve ever heard. Cancel that. Give me $20 on 20 to win.”
Ticket Writer: “Okay, $20 on Flying Private.”
Me: “Beautiful! Now that's the name of a winning horse.”

Of course Mine That Bird won the race in spectacular fashion, becoming the biggest Kentucky Derby longshot to win in over 100 years — and I cried into my Colt 45 for having talked myself out of a cool grand.

Flying Private? He finished dead last.

I’m not making this mistake again. On the 10th anniversary of this upset, give me the stupidest name, a nice post position and crazy odds.

Travis Reed: Under 0.5 Mint Juleps Consumed (Off The Board)

Derby Day is a national holiday. Get dressed up and bet a bunch of money on a sport you don’t follow 364 days a year. Women wear hats that would make Burt Reynolds jealous on Celebrity Jeopardy. Everyone is having a good time whether you are on the infield in Louisville or just at a watch party with friends.

The problem is that mint juleps have become the staple for these parties. And I have to let you in on a secret: mint juleps are trash. Let’s take a perfectly good bourbon and then sweeten it and crush a spinach salad on the bottom. Stop this madness.

You know what goes really well with bourbon? A glass.