5 Shocking Details From Travis Kelce’s 2024 Kentucky Derby Trip: The $100K Near-Miss And His New Horse Racing Obsession

Travis Kelce’s off-season adventures continue to make headlines, and his trip to the 150th Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 4, 2024, was no exception. The Kansas City Chiefs tight end traded his football helmet for a fedora and a dapper suit, diving headfirst into the "Run for the Roses." This wasn't just a celebrity appearance; it was an immersive experience that saw Kelce win big, lose bigger, and ultimately develop a passion so profound it led to a major investment in the world of horse racing, all while keeping the world guessing about his superstar girlfriend, Taylor Swift.

The annual spectacle of the Kentucky Derby is a collision of high fashion, celebrity glamour, and intense sports betting, making it the perfect stage for the larger-than-life personality of "Killa Trav." From his bold sartorial choices to the heart-stopping photo finish that cost him a six-figure payday, Kelce’s day at the historic track provided enough fresh, unique content to fuel his popular "New Heights" podcast and cement his status as a true Renaissance man of the sports and entertainment world.

Travis Kelce: Biography & Professional Profile

While his personal life often dominates the news cycle, Travis Kelce is one of the most decorated and dominant players in modern NFL history. He is a key figure in the Kansas City Chiefs dynasty and a burgeoning media mogul.

• Full Name: Travis Michael Kelce
• Date of Birth: October 5, 1989 (Age 36 as of December 2025)
• Hometown: Westlake, Ohio
• High School: Cleveland Heights High School
• College: University of Cincinnati
• NFL Draft: 2013 / Round 3 / Pick 63 by the Kansas City Chiefs
• Current Team: Kansas City Chiefs (KC Chiefs)
• Position: Tight End (TE)
• Jersey Number: 87
• Career Highlights:
  • 3x Super Bowl Champion (LIV, LVII, LVIII)
  • 9x Pro Bowl Selection (2014–2022)
  • 4x First-team All-Pro (2016, 2017, 2018, 2020)
  • NFL 2010s All-Decade Team
  • Holder of the NFL record for most consecutive 1,000-yard receiving seasons by a tight end (7)
• Media Ventures: Co-host of the highly successful "New Heights" podcast with his brother, Jason Kelce.
• Notable Relationships: Dating pop superstar Taylor Swift since 2023.

The Dapper Derby Look: A Bold Fashion Statement

The Kentucky Derby is as much about the fashion as it is about the horse race, and Travis Kelce certainly understood the assignment for the 150th running of the event. Kelce arrived at Churchill Downs on May 4, 2024, in a look that immediately sparked discussion among fashion critics and fans alike.

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He opted for a striking white pinstriped suit, a bold choice that deviated from the more traditional dark suits often seen in the exclusive boxes. The suit was complemented by a dark fedora, a staple accessory for the Derby, and a pair of sunglasses.

The overall aesthetic was described by some as "dapper" and "Kill Trav" personified, while others offered humorous commentary on his unique sense of style. Regardless of opinion, Kelce’s fashion choice was a clear signal that he was embracing the grand tradition and celebratory atmosphere of the historic event, setting a high bar for celebrity attendees.

A Near $100,000 Payout: The Heartbreak of a Photo Finish

One of the most talked-about moments of Kelce’s Derby experience was his foray into high-stakes sports betting. During an episode of the "New Heights" podcast, Kelce revealed the incredible story of his near-miss on a massive payout.

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He started the day with a win. Kelce successfully placed his very first bet at the Kentucky Derby, which was a celebrated moment captured on video. However, it was his second, much larger wager that provided the drama.

Kelce placed a significant bet on a trifecta—picking the top three horses in the correct order—for the main race. The 150th Kentucky Derby race, won by Mystik Dan in an incredibly close finish, ended in a rare photo finish, one of the closest in the race's history.

Kelce’s horse came up just "a nose short" of the winning position he needed, costing him a potential six-figure payday. He later recounted the agonizing moment, stating, "I almost f**king won," and estimating the lost winnings at $100,000. This dramatic betting story perfectly encapsulated the excitement and heartbreak of the sport for the NFL star.

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The New Obsession: A Racehorse with a Taylor Swift-Inspired Name

Perhaps the most significant and long-lasting outcome of Travis Kelce’s 2024 Kentucky Derby visit was the spark of a brand-new passion: horse racing.

Kelce was so "enamoured" by the atmosphere and the sport itself that he wasted no time in getting involved. He partnered with high-profile horse trainer Brad Cox and purchased a racehorse.

In a move that delighted "Swifties" and racing fans alike, Kelce named his new racehorse with a clear nod to his girlfriend, Taylor Swift. The horse is named "A Long Story," a reference to Swift's song "Long Story Short" from her album *Evermore*.

This purchase marks a major new venture for the Super Bowl champion, transitioning from a casual celebrity attendee to an owner in the competitive world of thoroughbred racing. The horse, trained by Cox, who has worked with former Kentucky Derby winning-jockey Luis Saez, is a serious investment, solidifying Kelce’s deep dive into his latest off-season hobby.

Swift’s Absence and the Celebrity Buzz

Leading up to the event, speculation was rampant about whether Taylor Swift would join Travis Kelce at Churchill Downs. Given their high-profile relationship and her strong track record of supporting him at major events, many expected the pop icon to make an appearance.

Ultimately, Taylor Swift did not attend the 2024 Kentucky Derby. Kelce, however, was not alone. He was spotted with a number of friends and fellow celebrities, enjoying the event and the exclusive atmosphere.

His presence alone was enough to generate massive media attention. He was reportedly given a "President Escort" to navigate the massive crowds at the 150th running of the Derby, a testament to his global celebrity status. Despite Swift's absence, her influence was still felt, not only in the rampant speculation but also through the phone call Kelce made to her to share the joy of his first winning bet. Furthermore, the news of his horse named "A Long Story" ensured that the "Kelce-Swift" connection remained the central narrative of his Derby experience, even without her physical presence.

Kelce's weekend at the Kentucky Derby was a perfect blend of high-profile celebrity attendance, high-stakes sports action, and a surprising personal development that has now tied him permanently to the world of horse racing. From a stylish suit to a near six-figure win and the purchase of a new racehorse, the Chiefs tight end proved once again that he knows how to make the most of his NFL off-season.