Alex Bregman and wife Reagan relive their love story in Aspen as Walker Buehler and his wife join the winter trip

Chicago Cubs third baseman Alex Bregman is enjoying his offseason with his wife Reagan Elizabeth Bregman in Aspen, Colorado, where the couple attended the 2026 X Games this week. The trip came just days after Bregman signed a five-year, $175 million contract with the Chicago Cubs in January 2026. The couple were not alone. They were joined by MLB pitcher Walker Buehler and his wife McKenzie Buehler. Reagan posted Instagram stories documenting amusing events on the trip, including a mirror selfie with McKenzie and a flashback to the site where Alex proposed to her in January 2020. Giving admirers a peek at their laid-back winter vacation, Alex also shared X Games images.Alex Bregman and Reagan Elizabeth spent time walking around Aspen, watching X Games events, and enjoying the snowy views. On her Instagram story, Reagan posted a picture from the spot where Alex proposed to her six years ago and wrote, “All the mems from where we got engaged.” The post quickly caught fans’ attention because it showed a softer side of the Cubs’ new star just weeks after his big contract news.Reagan also shared a mirror selfie with McKenzie Buehler, showing the close bond between the two couples. Alex later posted photos with Walker Buehler and McKenzie and simply wrote “X Games.” The short caption matched the easy, laid-back mood of the trip.Alex and Reagan first met when he was playing for the Houston Astros. They got engaged in January 2020 and married in December 2020. Since then, Reagan has often been seen supporting Alex at games and team events. This Aspen visit showed that even with a huge new deal and a new team, the couple is still making time for memories. Alex Bregman’s move to the Chicago Cubs is one of the biggest MLB stories of the offseason. The Cubs finished the 2025 regular season 92–70 and reached the National League Division Series, where they lost to the Milwaukee Brewers. The front office moved fast in January 2026 to add power and experience, and Bregman became the center of that plan.After the signing, Cubs All-Star shortstop Dansby Swanson spoke about Bregman’s impact. Speaking to The Athletic, Swanson said, “Alex is somebody that I’ve admired for a long time… I feel like my game could benefit more from playing with him than almost anyone else.”With Bregman set to play third base, Chicago is adding a two-time World Series champion who is known for both his bat and his leadership. While fans are watching his on-field role closely, this Aspen trip showed a lighter moment in a very busy month of his life, balancing baseball, friendship, and family time.