After the way the 2025 season ended, many expected Jazz Chisholm Jr to have one of the best offseasons and get a contract extension from the Yankees. Although he has not gotten the extension, he has some good news, and this might just change his future in baseball and life.

Jazz Chisholm Jr and his girlfriend Anyssa Santiago just announced that they got engaged, and the whole internet is going crazy over this ‘ship’.

Anyssa Santiago on X posted a few pics with Jazz Chisholm Jr and wrote, “My honey pie, aka future hubby.” Chisholm Jr reposted this saying, “MacChisholm.”

Anyssa Santiago, known professionally as Ahna Mac, is a rising recording artist today. She is best recognized for songs like Bed Head and Forever Sorry today. Her track Run It has passed 1M streams and continues gaining listeners steadily. She graduated from Linden High School in 2018.

Jazz Chisholm Jr. finished 2025 with 31 homers, 31 steals, and .813 OPS. He recorded 4.2 WAR and earned his first Silver Slugger award. The Yankees appear lukewarm on an extension, and no talks have started yet. New York hopes Ahna Mac brings momentum and confidence as contract pressure grows slowly.

Jazz Chisholm Jr and Ahna Mac now stand at a very interesting crossroads together. Their timing feels almost cinematic, and fans are watching like it’s postseason baseball again. If love truly boosts performance, then the New York Yankees might finally regret waiting on that extension.

Yankees fans hope this good news brings the best out of Jazz Chisholm Jr

The New York Yankees fanbase has seen plot twists, but this one feels oddly entertaining. At a time when contract talks feel colder than a Bronx April night, Jazz Chisholm Jr somehow finds the spotlight again. And yes, singer Ahna Mac is part of the story now. It seems the offseason refuses to stay quiet, and New York is watching closely.

Jazz Chisholm Jr posted career highs in 2025 despite the Yankees falling short again. A fan wrote, “My goat 40/40 next year,” and the internet smiled wide. Chisholm has progressed yearly, and 2026 could unlock a potential 40/40 jump huge milestone. With confidence rising and life-changing, he might follow his momentum next season.

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A fan simply commented, “My man stay winning,” and the reaction felt universal. The message captured both the congratulations and the belief that success follows Chisholm everywhere. With a new chapter starting, his supporters expect the wins to keep stacking naturally.

One fan joked, “This shit just made me want a shorty,” and everyone laughed. The comment showed a little envy but mostly admiration for Jazz Chisholm Jr and Ahna Mac. Moments like this remind fans that baseball and life both deliver surprises.

Fans quickly flooded the post with “Congratulations!!!” celebrating Jazz Chisholm Jr and Ahna Mac. The simple comment reflected excitement and shared happiness across the Yankees and music communities. Messages like this show how much supporters appreciate milestones both on and off the field.

A fan commented, “Congrats, Jazz, you guys are adorable,” showing support for the couple warmly. The message highlighted excitement over Jazz Chisholm Jr and Ahna Mac’s engagement announcement online. Moments like this unite followers, blending enthusiasm for baseball achievements with personal milestones beautifully.

Jazz Chisholm Jr and Ahna Mac now command attention both on social media and in baseball. Their engagement proves life off the field can capture headlines as fiercely as home runs. If momentum translates into performance, Yankees fans might finally see Chisholm earn the contract he deserves.