Bears S Jonathan Owens cashes in on his first-ever bet at the Kentucky Derby

Chicago Bears safety Jonathan Owens had a lucky Day 2 at the 2025 Kentucky Derby. Taking to Instagram, he shared his excitement after winning several bets on the horse Spirit of St. Louis, who won the Old Forester Bourbon Turf Classic.

Owens posted a video of himself erupting in joy.

“When Spirit of St. Louis won, my 4th bet in a row," read the caption.

The horse was ridden by jockey Manny Franco. Manny pushed through a crowded field on a wet, muddy track to win the race by three-quarters of a length. Later, in another Instagram Story, Owens joked about his winning streak.

“Picked the right horse for the Derby too, insane. 🤦‍♂️😂 People just started asking me who I was picking," he wrote.

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Jonathan Owens and Simone Biles' fashion game at Kentucky Derby was A+

Jonathan Owens and his wife, Simone Biles, made a stylish appearance at the 2025 Kentucky Derby. Both turned heads with their matching lavender outfits.

To get into specifics, Biles wore a sequined lavender dress with a matching hat. Meanwhile, Owens sported a purple suit jacket, white trousers and a coordinating hat.

The superstar gymnast also had the honor of delivering the traditional "Riders Up" call, which signals jockeys to mount their horses before the main race.

For the first day of the 2025 Kentucky Derby weekend, Simone Biles wore a cream strapless mini dress with frayed edges. She added black tights and a big black headpiece, which gave off a classy "Breakfast at Tiffany's" vibe. Biles finished her look with a Givenchy necklace.

On the other hand, Jonathan Owens matched her style in an olive green suit with a black T-shirt. He also wore diamond chains and a black belt.

Together, they looked like a power couple and stood out at the Barnstable Brown Gala, which is one of the top events before the Derby.

Jonathan Owens and Simone Biles got married in April 2023. First, they had a small courthouse wedding in Houston, Texas. It was a simple and private ceremony where they officially became husband and wife.

One month later, they had a big celebration in Cabo San Lucas, Mexico. The second wedding was held at the Nobu Los Cabos Hotel with 144 guests