Chicago Cubs third baseman Alex Bregman’s wife, Reagan Bregman, recently shared photos from Kentucky for the 2026 Breeders’ Cup. She wore a red maxi dress for the World Championships in Lexington on Oct. 30-31, a bright contrast to a crowd that, by the event’s own fashion guidance, leans on fall jewel tones and tailored coats, with purple as the official color.
Keeneland hosted the Breeders’ Cup for the fourth time, after 2015, 2020 and 2022, and the 43rd running closed with the $7 million Classic on Saturday. The trip fits a family that has been in racing since 2023.
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Reagan and Alex Bregman’s stable, Bregman Family Racing, entered the sport with eight horses and runs under the names of Alex, Reagan and his parents, Sam and Jackie. Reagan, a lifelong equestrian, picks most of the horses’ names.
Their rookie season brought a share of OwnerView’s New Owner of the Year award and a Breeders’ Cup starter in No Nay Mets, with the couple at the track to watch him run. Alex served as a Breeders’ Cup celebrity ambassador and pledged Breeders’ Cup earnings to the fight against antisemitism before the 2023 championships.
The photos came with a short caption: “Breeders Cup 2026 🐎🏆.” Racing has not been the only item on her calendar. She also shared a look at a football night out with Alex Bregman, one of the few recent posts with no ballpark in the background.
Alex Bregman’s Wife Reagan Shares Adorable Moments With Their Sons
Chicago Cubs star Alex Bregman’s wife, Reagan, shared glimpses into their daily lives with their two sons, Knox and Bennett, on social media. In one set of Instagram Stories images, the boys are photographed from behind on a brick path while trick-or-treating.
Knox was seen wearing a red-and-blue Spider-Man suit with a woven basket over one arm, while Bennett sported a red-and-black armored costume carrying a black treat bucket shaped like a face. Palm trees and cacti border the walk, an adult in a top hat and dark suit stands at the edge of the frame, and two red hearts were added to the image.
A second photo moves indoors. Knox donned a light blue T-shirt, standing in front of a wall-mounted television showing a baseball broadcast, one arm raised, with the broadcast’s on-screen graphic carrying Alex Bregman’s name. A dog appears at the bottom of the frame.
The family also spent time at Troubadour Golf & Field Club, according to a post of the four of them at the club. “Nothing better 🍂🤎,” Reagan captioned the Instagram post.
Bregman’s first season in Chicago went close to plan after the Cubs gave him a five-year, $175 million contract in January. He played 155 games, hit 28 home runs with 33 doubles and 93 RBIs, posted an .819 OPS, and his 5.8 WAR per Baseball Reference was his highest since 2019.
Edited by Kaushani Chatterjee
