The significance of the Kentucky Derby needs no reiteration. Many trainers and jockeys spend their entire lives striving to simply participate in the 151-year-old race. And no, that’s not an exaggeration. Take late trainer Larry Demeritte, who started from humble beginnings and ran in the 150th Derby for the first time at 75. Then there are those, like Mystik Dan’s trainer, Kenny McPeek.

In the same 150th Derby that saw Larry Demeritte’s horse, West Saratoga, finish 12th, McPeek created history with Mystik Dan. You see, McPeek had won the Kentucky Oaks, a Grade I stakes race for 3-year-old fillies, with his horse Thorpedo Anna, setting up Dan for a truly rare feat even among Derby winners. And on race day, McPeek’s colt achieved that rare feat, winning the race at Churchill Downs and giving his trainer the Derby Oaks Double crown.

And now, a year after that historic day, the trainer has finally fulfilled his promise. “I always said that if I ever won the Kentucky Derby, I would get a tattoo. Derby Oaks Double 2024. I DID IT!!” the iconic trainer for Thorpedo Anna and Mystik Dan posted on X. While he may have waited for a year to finally make good on his word, the 62-year-old didn’t hold back.

The massive artwork covered his entire upper arm, with ‘150’ written in golden ink to commemorate the special milestone. And besides the year and the words ‘Derby Oaks Double’, another highlight of the tattoo was a rose and a lily, the two flowers tied to the Derby with tradition. However, that tattoo didn’t depict everything that made the feat so special.

Winning the Kentucky Derby and the Oak made McPeek only the third trainer to win the double in the same calendar year. “To be included in the same breath as Ben Jones, someone that I’ve always really admired is special,” said the McPeek after winning the two races. I was also special because the 62-year-old had been trying to win the Derby for decades.

Before 2024, he came the closest with Tejano Run in 1995, and in the meantime, he won both the Preakness (2020) and Belmont Stakes (2002). Although Kenny McPeek couldn’t create that same magic in 2025, the fact that his horse ran this year was a miracle in itself.

Kenny McPeek’s unexpected Kentucky Derby entry

Despite landing the incredible achievement of winning the double, Kenny McPeek didn’t have a horse for the Kentucky Derby. While he had come to terms with that after Render Judgment finished in fifth place at the Toyota Blue Grass Stakes on April 8, fate has spun its yarn differently. On April 26, barely a week ahead of the 2025 Kentucky Derby, Tappan Street bowed out of the Derby.

The Florida Derby (G1) winner suffered a condylar fracture to his right front leg, and trainer Brad Cox pulled out of the competition. “He has a little crack. It does require surgery, and obviously, he is out of the Derby,” Cox said after his three-year-old got injured. While Coz had another horse in the race with Final Gambit, Tappan Street’s injury gave McPeek’s horse an entry into the race.

If that wasn’t miraculous enough, Render Judgement was also one of the last horses that late singer Tobie Kieth trained himself. “Here’s some sentiment here. This is one of the last horses owned by Toby Keith, the singer, and his family and I think they’re really excited about this and they should be,” McPeek said as Render Judgement frew 15 post.

Although the horse finished 16th, the dramatic entry and the sentiment of Toby Keith’s dream come true made the run special anyway. “It was Toby’s dream….Render Judgment is going to the Kentucky Derby. He worked so hard to finally have one there! Toby will have the best seat in the house to watch,” the late singer’s official page posted. Was it tattoo worthy? Probably not. Then again, McPeek’s run-out of space on his upper arm, anyway.