Alex Bregman's Romantic Winter Escape in Aspen Following Historic Cubs Contract
Chicago Cubs third baseman Alex Bregman is savoring the offseason in picturesque Aspen, Colorado, alongside his wife Reagan Elizabeth Bregman, creating cherished memories just weeks after inking one of baseball's most significant deals. The power couple attended the thrilling 2026 X Games this week, marking their first major outing since Bregman's career-defining move to the Windy City.
A Vacation Blending Romance and Friendship
The Aspen trip unfolded merely days after Bregman finalized a monumental five-year, $175 million contract with the Chicago Cubs in January 2026. The Bregmans weren't alone in their winter retreat; they were accompanied by close friends Walker Buehler, the accomplished MLB pitcher, and his wife McKenzie Buehler. This gathering highlighted the strong bonds between baseball families during the offseason break.
Through Instagram stories, Reagan offered fans an intimate glimpse into their relaxed vacation. She shared a playful mirror selfie with McKenzie Buehler, showcasing the camaraderie between the two couples. More poignantly, Reagan posted a nostalgic flashback to the exact Aspen location where Alex proposed to her in January 2020, captioning it with heartfelt sentiment about their engagement memories.
Revisiting Sentimental Moments Amid Snowy Landscapes
Alex Bregman and Reagan Elizabeth filled their Aspen days with leisurely walks through the snow-covered town, spectating at exhilarating X Games events, and soaking in the breathtaking winter vistas. Reagan's Instagram story from their engagement site particularly resonated with fans, revealing a tender, personal side of the Cubs' newest superstar shortly after his blockbuster contract announcement.
Alex complemented his wife's social media posts by sharing his own X Games photographs featuring the Buehlers, accompanied by a simple "X Games" caption that perfectly captured the trip's effortless, relaxed atmosphere. This balanced sharing painted a complete picture of their vacation blending sports, friendship, and romance.
From Houston Beginnings to Chicago's Bright Future
The Bregmans' love story began during Alex's tenure with the Houston Astros. Their relationship progressed from a January 2020 engagement to a December 2020 wedding, with Reagan becoming a constant presence at games and team events. This Aspen excursion demonstrates that despite Bregman's massive new contract and transition to a new team, the couple continues to prioritize meaningful moments together.
Bregman's move to the Chicago Cubs stands as one of the most impactful MLB stories of this offseason. The Cubs, coming off a 92–70 regular season in 2025 and a National League Division Series appearance against the Milwaukee Brewers, aggressively sought to bolster their lineup with power and experience in January 2026, making Bregman the cornerstone of their strategic vision.
Teammate Endorsement and On-Field Expectations
Following the signing, Cubs All-Star shortstop Dansby Swanson expressed enthusiastic support for his new teammate. In an interview with The Athletic, Swanson remarked, "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." This endorsement underscores the respect Bregman commands within baseball circles.
As Bregman prepares to anchor third base for Chicago, the Cubs gain a two-time World Series champion renowned for both his offensive prowess and clubhouse leadership. While fans and analysts closely monitor his on-field integration, this Aspen vacation revealed a lighter, personal dimension during a hectic period of his life, beautifully balancing professional commitments with cherished personal connections.
