How TheLines’ Staff Is Betting $100 On The Kentucky Derby

Written By Brett Gibbons on May 5, 2023
Kentucky Derby betting

The Greatest Two Minutes In Sports are nearly upon us as the 2023 Kentucky Derby runs Saturday. Annually one of the most-bet on sporting events in the world, TheLines staff tries their hand at betting on the Kentucky Derby. How would each of them spend $100 on the Run for the Roses? We compiled some bet cards below.

You may find a few bets below that you hadn’t considered betting, or you might just get confirmation of a direction you were leaning. Barring any more scratches, let’s dive in.

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How TheLines Staff Is Betting $100 On The Kentucky Derby

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Stephen Andress

Find Stephen’s full bet card and a handy guide on picking a Kentucky Derby winner here.

Dave Bontempo

  • $50 to win: Forte (15)
  • $10 exacta Box: Forte and Angel of Empire (15-14)
  • $2 trifecta key: Forte and Angel of Empire in first two spots (15-14). Kingsbarns and Tapit Trice in third (6-5). ($8 total)
  • $0.50 trifecta box: Forte, Angel of Empire, Mage and Raise Cain (15-14-8-16, $12 total)
  • $1 trifecta: Forte over Angel of Empire, Derma Sotogake and Mage (15-14-17-8, $6 total)
  • $2 exacta box: Forte and Mandarin Hero (15-22)

*Reaches for another $100*

Andrew Champagne

You can still extract value from this race even if you think #15 Forte will be tough to beat (and I do).

Over the years, Kentucky Derby exactas have overpaid in a big way. The best example came in 2013, when 5-1 favorite Orb won and 34-1 shot Golden Soul came in second. The $2 exacta paid $981, even with the chalk on top. That’s the scenario I’m hoping unfolds this Saturday.

$20 Exactas: 15 with 8, 14, 17, 22 ($80 total)

My primary play uses Forte on top of four others. Two will take some money. #14 Angel of Empire won the Arkansas Derby impressively, while #17 Derma Sotogake is probably the best 3-year-old Japan has ever sent to contest America’s most well-known horse race.

The other two will be longshots. #8 Mage ran second to Forte in the Florida Derby and had trouble of his own, while #22 Mandarin Hero gets to run thanks to a few scratches. That one shipped from Japan to California, ran a hard-luck second in the Santa Anita Derby (beaten just a nose), and should be moving the right direction late.

$4 Exactas: 8, 14, 17, 22 with 15 ($16 total)

These are “saver” plays, just in case Forte runs second behind a bigger price I happen to be using. If Mage or Mandarin Hero wins and Forte runs second, for instance, I want to get paid.

$2 Exactas: 15 with 16, 18 ($4 total)

Finally, I’ll throw a few bucks at two combinations that will pay too much to not have in some form or fashion. #16 Raise Cain had a sneaky-bad trip when fifth in the Blue Grass, and his win in the Gotham was very impressive. Meanwhile, #18 Rocket Can ran second to Forte in the Fountain of Youth and has been working very, very well since shipping to Churchill Downs.

Brett Gibbons

$10 Exacta Box: Forte, Tapit Trice, Mandarin Hero (JPN), Verifying (15-5-23-2, $40 total)

Full disclosure: I followed in Stephen’s steps when it came to picking winners. All four of these horses meet the criteria for a Derby winner and I want a chance at each of them to finish in the top two, in any order. The addition of Mandarin Hero (JPN), though lightly-raced, is a welcome one that I want a piece of this year.

$20 Outright win: Forte (15)

Originally, I wanted to take a crack at a longer longshot, which was Skinner. However, he’s out of the Derby, alongside Practical Move, Continuar (JPN), Lord Miles, and Blazing Sevens. All of the withdrawals makes this field a lot lighter than it was, really coming down to a handful of horses that stand out.

Forte was a strong favorite on the morning line odds and has a pretty favorable gate position, 15. Though his Brisnet speed figures are trending in the wrong direction, Forte is a deserved favorite. A favorite in a weakened field feels like a strong bet.

$2 Superfecta Box: Forte and Angel of Empire (15-14, first and second), Tapit Trice and Two Phil’s (5-3, third and fourth), $8 total

I want a share of most of the favorites, even if they don’t fully meet the criteria Stephen laid out before. It rarely pans out, but when dealing with a bunch of bets, it’s good to have a share of the chalk.

$1 Trifecta Box: Forte, Angel of Empire, Derma Sotogake (15-14-17, $6 total)

There’s been a lot of rumblings that Derma Sotogake is the best horse Japan’s ever sent to the Kentucky Derby. All signs point to them producing a winner with their recently-revamped colt training, so why not this year? Taking a flier on Derma Sotogake to hit the podium alongside two of the favorites in this race.

$1 Trifecta Box: Tapit Trice, Angel of Empire, Mandarin Hero (5-14-23, $6 total)

Almost never does the podium consist of three longshots, but what if Forte doesn’t finish in the top three? I’d like to hedge that outcome since “foregone conclusions” have had a rough run the last four races.

$15: A Mint Juliep

I mean, come on. It wouldn’t be Derby Day without one. I’ll use the remaining $5 to tip the bartender.

Matt Burke

$50 To Show: 6 ($50), $30 To Win: 6 ($30)

Forte is a deserving favorite having had the spotlight on him since November’s Breeders’ Cup Juvenile. But with 19 horses in the Derby field, I rarely like to go with the favorite to win. There’s just too much unpredictability with that many ponies.

I will, though, toss Forte into some exotics and hope that he (mostly) lives up to the hype.

The horse I like the most in this field is Kingsbarns at 12-1. The colt does not have the best post position, historically (Post 6 has just 2 wins, 8 seconds and 3 thirds in 93 starts), but I don’t pay much attention to post position when it comes to the Derby and its large field. We’ve seen horses in high post positions win recently (Rich Strike at 20 last year, Country House at 18 in 2019) and low post positions win recently (Always Dreaming at 5 in 2017 and California Chrome at 5 in 2014).

The main reason for excitement around Kingsbarns is simply because he’s undefeated. Todd Pletcher’s horse is 3-for-3 on three different tracks.

$4 Exactas: 6 with 15, 8, 12, 17 ($16)

Again, the 20-horse field scares me from blowing most of my budget on one horse to win. I usually go with larger Show bets for the Derby.

And while Kingsbarns jockey Jose Ortiz has never finished first at the Derby, he has finished in the money twice.

$4 Trifecta: 6, 15, 5 ($4)

Shots in the dark with combos including the likes of Forte, Mage, Jace’s Road, Derma Sotogake and Tapit Trice.

Mo Nuwwarah

I am ready to lose my (mostly) theoretical $100 on the Derby once again. Using my extremely scientific method of collating multiple tout sources, mainly my dad who has been playing horses for 40 years, I’ve come up with the horses I’m backing.

My key horse is going to be Angel of Empire. This horse has the pedigree, the trend (faster in each of last four), and the results (back-to-back stakes wins against Derby contenders) to hopefully pull the mild upset over Forte. It also has a top trainer and jockey in Brad Cox and Flavien Prat. Going off as one of the favorites, I’ll put a large chunk of my stake here.

Stephen and his numbers have convinced me that Mandarin Hero (JPN) has a shot. This horse also excelled in a strong field at the Santa Anita, running second to the scratched Practical Move. A little on Mandarin Hero for a longshot win.

It seems like the inside post horses are generally at a disadvantage in a crowded field. So, to round out a trifecta box with Angel of Empire and Forte, I’m including Kingsbarns (my dad’s favorite longshot) and Mage.

Finally, let’s try to get rich with a $1 super. Japan comes to play.

  • $40 to win: Angel of Empire
  • $10 to win: Mandarin Hero
  • $1 Trifecta box: Angel of Empire, Forte, Mage, Kingsbarns)
  • $1 Superfecta: Mandarin Hero, Forte, Angel of Empire, Derma Sotogake

I’ll need the other $25 for beer after I get waxed.

TheLines Free Kentucky Derby Challenge

2023 Kentucky Derby Odds

Post Position NumberHorse NameKentucky Derby OddsMorning Line OddsClosing Line OddsTrainerJockey
1.Hit Show25-130-124-1Brad CoxManny Franco
2. Verifying15-115-114-1Brad CoxTyler Gaffalione
3. Two Phil's8-112-19-1Larry RivelliJareth Loveberry
4. Confidence Game17-120-121-1Keith DesormeauxJames Graham
5.Tapit Trice9-25-19-2Todd PletcherLuis Saez
6.Kingsbarns10-112-111-1Todd PletcherJose Ortiz
7.Reincarnate13-150-114-1Tim YakteenJohn Velazquez
8. Mage17-115-115-1Gustavo DelgadoJavier Castellano
9.SkinnerSCRSCRSCRJohn ShirreffsJuan Hernandez
10.Practical MoveSCRSCRSCRTim YakteenRamon Vazquez
11.Disarm24-130-127-1Steve AsmussenJoel Rosario
12.Jace's Road31-150-133-1Brad CoxFlorent Geroux
13.Sun Thunder30-150-133-1Kenny McPeekBrian Hernandez Jr.
14.Angel of Empire4-18-14-1Brad CoxFlavien Prat
15.ForteSCR3-1SCRTodd PletcherIrad Ortiz Jr.
16.Raise Cain31-150-133-1Ben ColebrookGerardo Corrales
17.Derma Sotogake8-110-17-1Hidetaka OtonashiChristophe Lemaire
18.Rocket Can27-130-128-1Bill MottJunior Alvarado
19.Lord MilesSCRSCRSCRSaffie Joseph Jr.Paco Lopez
20.ContinuarSCRSCRSCRYoshito YahagiRyusei Sakai
21.Cyclone Mischief29-130-129-1Dale RomansTBA
22.Mandarin Hero20-120-117-1Terunobu FujitaKazushi Kimura
23. King Russell31-150-132-1Ron MoquettRafael Bejarano
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Written by
Brett Gibbons

Brett is an avid sports traveler and former Division-I football recruiter for Bowling Green and Texas State. He’s a graduate of BGSU and works as an auditor for Google content curation products. He’s also contributed to Sports Illustrated and Fansided during his young writing career.

View all posts by Brett Gibbons