Jazz Chisholm Jr. is closing out the offseason with momentum that reaches well beyond baseball. He marked a major personal milestone during a holiday trip that quickly captured fans’ attention.
Jazz Chisholm Jr. proposed to his girlfriend, Ahnalys Santiago, on Christmas Day while the couple was vacationing in Finland, creating a dramatic, intimate scene beneath the Northern Lights. The engagement was revealed through a joint Instagram post that showed Chisholm dropping to one knee as the green glow of the aurora lit the night sky, with the couple bundled up against the cold and celebrating moments later with a kiss.
Santiago, 25, shared her emotional reaction in a lengthy caption that quickly went viral. “I’m not Da Gurl anymore yallllll I’m DA WIFEEEEEEEE… I can’t stop crying,” she wrote. “I love you so much… you tricked me @_jazz3. I guess when you know, you know.” In a follow-up comment, she added, “Y’all, he really brought me across the world for this… I’m exactly who I think I am.”
The images from the proposal sparked an immediate flood of congratulations from fans, teammates, and athletes. Chisholm shared celebratory Instagram stories from friends, while Santiago displayed her engagement ring — a cushion-cut diamond on a twisted band — in close-up photos.
Santiago, who also goes by Ahna Mac, has built a public profile through music, visual art, and reality television appearances, including roles on the “Baddies” franchise. Despite her growing following, the couple has largely kept details of their relationship private. While it remains unclear exactly when they began dating, Santiago shared a photo from Yankee Stadium in October, offering one of the few early public glimpses into their relationship before the engagement announcement.
The proposal occurred just days before the couple posted a playful, holiday-themed update on social media. This timeline highlights the expressive, confident public personas both have embraced. For Chisholm, known for his flair and energy on the field, the engagement signified a quieter but deeply meaningful chapter of his life during the offseason.
This milestone comes at a transitional time for Chisholm, as he enters a pivotal offseason following a year that fell short of expectations for the New York Yankees. While New York entered the postseason with championship hopes, the team was eliminated early, losing 3-1 in the American League Division Series to the Toronto Blue Jays. The disappointing finish has left the organization evaluating its roster and future direction.
Despite the team’s struggles, Chisholm individually delivered a historic season. He became just the third player in Yankees history to record at least 30 home runs and 30 stolen bases in a single year, a feat that underscored his rare combination of power and speed. The performance is expected to result in an arbitration salary increase this offseason, adding another layer of significance to the months ahead.
Speculation has emerged about Chisholm’s long-term future in New York. He has just one year remaining on his contract. Some observers have questioned whether he could be involved in a potential “challenge” trade, a concept general manager Brian Cashman has referenced when discussing roster flexibility. Cashman, however, pushed back on the notion that Chisholm is expendable.
“He’s someone who I think is part of the solution,” Brian Cashman said during the winter meetings. “Someone who’s made us better since getting him two deadlines ago, giving us athleticism.”
As spring training approaches, Chisholm’s focus will soon shift back to baseball, where expectations remain high for both him and the Yankees. Still, the engagement represents a moment of personal clarity and celebration during an offseason often dominated by uncertainty, rumors, and pressure.
For now, though, Chisholm is savoring a different kind of victory. Under the glow of the Northern Lights, he began a new chapter—one defined not by statistics or standings, but by a commitment that, as Santiago’s words made clear, carries just as much meaning as anything he has accomplished on the field.
