I’m Making These 3 Bets, Longshot Picks For 2023 Preakness Stakes

Written By Jack Flaherty on May 17, 2023
Best bets longshot picks 2023 Preakness Stakes, from playma.com

The 134th running of the Preakness Stakes will be upon us this Saturday, May 20. Known as the run for “The Black Eyed Susan,” the race takes place at storied Pimlico Race Course in Baltimore, Maryland.

The post time is forecasted to be at 6:50 p.m. and to be carried by horse racing faithful broadcast partner, NBC

The great news is that we have a serious Triple Crown contender this year, Mage, who recently won the Kentucky Derby in style. If Mage wins Saturday, this will set up a dramatic Belmont Stakes in June. Mage is the only returning Derby starter, which means he will be facing fresh legs or “New Shooters” in this year’s field of eight.

Even with legal US sportsbooks live in Massachusetts, horse betting in Massachusetts is still extremely popular, and the Preakness is expected to draw a lot of action.

From one Massachusetts horse bettor to another, here are my picks for the 2023 Preakness Stakes.

Handicapping the 2023 Preakness

Below, I list the post number with the horse, trainer, results of their last race and odds. In the parenthesis next to the horse, I list a Best Beyer number. This is a rating of their fastest race. A 100 Beyer is really good. An 83 Beyer is not.

1. National Treasure (97)

Trainer: Bob Baffert

Last race: Santa Anita (4th)

Odds: 4-1

We thought we were going to have more from this Bobby-Bob-trained colt. Third last year in the BC Juvenile; afterwards we all said, here we go, another Baffert live one. But Treasure has not progressed. Another third in the G3 Sham in January, then nothing. Withdrew from the Sam Philipe because he hurt his footsie-wootsie, and then fourth in the Santa Anita Derby

Fourth at Santa Anita is not terrible, especially coming off a layoff, but like I said, we had expected more.

The 1-post will not hurt him — watchers expect Treasure to run straight out and set a decent pace. Mage would appreciate it. Somebody has to get out front and do something and not let the race get off slow. 

National Treasure is at 4-1 because horse people know he comes from good family stock and now, perhaps, has fully recovered from injuries, maybe this is his time. We’ll see.

At 4-1 and only 1-for-5 lifetime so far, I will pass. In a field this modest, I can only support one pony.

RELATED: Here’s How I Did With My Kentucky Derby Bets

2. Chase the Chaos (83)

Trainer: Ed Mogan

Last race: Cal Derby (8th)

Odds: 50-1

Won El Camino Real, which punched his Preakness ticket. That was a while ago.

Ah … Ed? You do know that the Preakness is run on dirt, right? Why are you keeping your boy training in Oakland on synthetic Tapeta at Golden Gate? Why didn’t you take Chaos to Baltimore last week and get him practicing on Pimlico dirt? 

I know your colt has a slim chance of cashing a purse check, but I also have a list of some Motel 6s nearby. But be optimistic, Ed, last year the Preakness paid $40,000 for fifth place. You are only three scratches away.

3. Mage (105)

Trainer: Gustavo Delgado

Last race: Kentucky Derby (1st)

Odds: 8-5

Deserving odds-on favorite with his impressive victory and a 105 Beyer at Churchill. Horse racing badly wants Mage to win the Preakness and set up a potentially great Belmont. There we might find my Angel of Empire, perhaps even the return of the No. 1 ranked 3-year-old, Forte, coming off the injured vet list. 

With any luck, can we see the former top ranked 3-year old, Arabian Knight? The last we saw of Knight was back in February when he crushed the field in the slop at Oaklawn’s Southwest. Not too long after that victory, Baffert took him off the Derby trail. Bobby-Bob, what did you do with him? You haven’t killed him yet, have you? 

Tell me again what happened to your Medina Spirit? If Arabian Knight is sound, can you please get him to New York? As I have just written, in this limited field, I can only support one colt. I must pass.

But go, Mage, go!

ALSO READ: FanDuel Racing vs. DK Horse In Massachusetts: Which Is Better?

4. Coffeewithchris (88)

Trainer: John Salzman Jr.

Last race: Tesio (5th)

Odds: 20-1

Where do people come up with these names? And why all one word? Coffee might want to stick his nose out front at some point early, but he won’t last. His Best Beyer 88 was a one-turn. He’s not so good when the races get longer. Pass.

A quick interject — the official Preakness flower is the Black Eyed Susan. Long decades ago, little brother noticed that the Derby had an official flower and the “Run For the Roses.” So the Preakness wanted one. They chose Susans, the official state flower of Maryland. 

But those geniuses of yesteryear did not realize Black Eyed Susans are a July flower and their horse race runs in May. Oh. So they borrowed Viking Daisies and painted them. No problem. And to this day, no Susans have ever been seen on Preakness Day (unless cryogenically frozen).

5. Red Route One (92)

Trainer: Steve Asmussen

Last race: Bath House (1st)

Odds: 10-1

I call Asmussen “Needles” because he was caught on tape by the PETA organization administering something. He beat the rap by claiming it was only vitamins and/or legal hormone supplements, and he dared people to prove otherwise.

Despite being cited for 22 past vitamin violations, this guy still trains. Red Route One is a decent horse. Won last at Oaklawn and I saw him make some impressive fast closing efforts in the stretch this spring.

He is indeed a closer but the horse is not very fast. In order to run down tired ponies late, he will need a fast early pace.

Doubt he will get it. Pass.

6. Perform (85)

Trainer: Shug McGaughey

Last race: Tesio (1st)

Odds: 15-1

Despite being of Irish descent, I can never figure out how the Irish sprinkle consonants throughout their names. Perform is interesting. The owners put up a $150,000 nomination fee to enter him in the Preakness after his recent win at Laurel in the Tesio Stakes. Now, if they had a more proper belief in their colt in January, that fee would have been $600. Oh ye of little faith. 

To be fair, the number of thoroughbred foals is around 40,000 a year. Of that, only about 1% of owners put up the $600. Therefore, 99% of owners have more limited aspirations.

Anyway, if you ever get real lucky, such as buying a Funny Cide, then you will have a second chance to nominate and submit your fee before the end of March, then pegged at $6,000. After that, it becomes big bucks. 

As far as Shug’s horse, Perform, no, I am looking elsewhere.

Would love to see Shug win, but must stay away. However, if someone is looking for a decent longshot, a longshot who might have just won his last Maryland start, then I have seen worse bets. 

7. Blazing Sevens (93)

Trainer: Chad Brown

Last race: Blue Grass (3rd)

Odds: 6-1

Despite trainer Chad Brown having won two recent Preakness races, and despite also picking up the unemployed top jock, Irad Ortiz Jr., I don’t see it. Sevens had his chance in the Blue Grass with the race directly in front of him late, but he never made a serious move. Even with Irad, who lost his mount from the medically suspended top colt Forte, it’s not enough.

Going elsewhere.

8. First Mission (98)

Trainer: Brad Cox

Last race: Lexington (1st)

Odds: 5-2

Loved his father, Street Sense, when he raced. First Mission seems to me a late bloomer. He was solid in his past two races around two turns and his pedigree says he likes it long. I have had Cox ponies all spring and am not jumping off the cart now. This is my boy. I will be betting him somewhere on my FanDuel Racing Massachusetts app.

My Preakness bets

My favorite Preakness bet: $100 on the nose.

This is not a complicated race to bet. Since I have decided on No. 8 First Mission, then I will funnel my wages to him. I can’t see doing exactas or trifectas. 

If First Mission pulls it off, then it’s also likely Mage will be close behind and that combo won’t pay more than crumbs. No, $100 on the nose for No. 8 First Mission to win. No place bets and certainly no shows.

And no trifecta box bets either since common sense again tells me I would have to use both Mage and First Mission, and so I ask myself, how can you win any money on that? Include a long-longshot?  But who? No. 2 and No. 4 are hopeless.

No, I’ll keep it simple. Bet well on No. 8 and play around with some trifecta key bets with No. 8 on top.

Trifeca keys another cheap betting option ($6)

Tri-key No. 8 with two or three horses underneath. That might work. But the key is First Mission must win. 

In a trifecta key, you pick one horse to win and a combo of horses to come in second and third.

It keeps the bet cheap and there’s potential for a nice payday if your longshots come in. A $1 tri-key with one horse up top and three underneath will cost you $6.

The no-Mage trifecta box ($24)

Now for that wager that cannot be spoken. The no-Mage trifecta-box.

Also called the Mage throws his jockey at the starting gate trifecta box.

With a heavy favorite in a smallish or modest field, I will sometimes bet a three- or four-horse trifecta without the big favorite. 

It’s a longshot bet, of course. Mage could beat some of this year’s competitors on just three legs. But still. A $1 trifecta box playing three horses is only $6 bucks. I expect, however, to play a no-Mage trifecta box with four ponies for $24 since I don’t want some hopeless wonder finishing third and spoiling my no-Mage tri-box. 

Closing thoughts

I heard that Baffert is mailing 3 of his horses to the East Coast by Federal Express via Newark. Then vanning them down to Baltimore. Interesting. Baffert, what are they charging you a pound? Be careful, FedEx, you are dealing with a noted horse-thief (Ask F. Springer, the real trainer of War Emblem) and a convicted drug cheater. Bobby-bob might even try to take their horse shoes off and put them in his personal carry-bag. One never knows about him.

So there you go.

If you or a loved one is experiencing problems with gambling, call 1-800-327-5050 or visit www.mahelpline.org/problemgambling to speak with a trained specialist for free, 24/7

Photo by AP Photo/Julio Cortez
Jack Flaherty Avatar
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Jack Flaherty

Jack Flaherty independently represented manufacturers in the Middle East and Africa for 29 years and is a lifelong horse racing fan who, on two occasions, successfully bribed the National Guard with cheap beer and hopped the fence to attend the 1974 and 1975 Kentucky Derby. Jack currently resides in Falmouth, Massachusetts.

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