After Bold Clip, Yankees' Jazz Chisholm Shares Engagement Video
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Home News Jazz Chisholm Jr.

Hours after viral video, Yankees’ Jazz Chisholm gets engaged to singer

Sara Molnick by Sara Molnick
December 27, 2025 at 4:53 am EST
in Jazz Chisholm Jr., News, Off The Field
Reading Time: 7 mins read
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Yankees' Jazz Chisholm proposed to his girlfriend, singer and reality television star Ahnalys Santiago, on 2025 Christmas Day

_jazz3@Instagram

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NEW YORK — Less than 24 hours after a provocative holiday video set the internet ablaze, Yankees star Jazz Chisholm made headlines for an entirely different reason.

This time, the 27-year-old infielder dropped to one knee.

Chisholm proposed to his girlfriend, singer and reality television star Ahnalys Santiago, on Christmas Day. The setting could not have been more dramatic. Snow covered the ground. The Northern Lights illuminated the sky above them. They were in Finland, thousands of miles from the Bronx.

Still gonna share my favorite moment of last night! My baby forever 🤍 #MacChisholm pic.twitter.com/Fzy1ikMbmr

— Jazz Chisholm Jr (@j_chisholm3) December 26, 2025

The couple shared photos and videos of the moment on Instagram on Friday. Santiago, who performs under the stage name Ahna Mac, did not hide her emotions.

“I’m not Da Gurl anymore yallllll I’m DA WIFEEEEEEEE,” she wrote. “I can’t stop crying. I love you so much. You tricked me. I guess when you know you know, and he ain’t playing bout me.”

Congrats to Jazz Chisholm on his engagement to Ahnalys Santiago 👏

(Via: @j_chisholm3) pic.twitter.com/EpimQ7Hkxi

— Complex Sports (@ComplexSports) December 26, 2025

The viral video that preceded the proposal

The engagement came after Chisholm and Santiago went viral for a different reason earlier in the day.

The couple posted a series of photos and videos from their Finnish getaway on Christmas Eve. They wore matching fuzzy green onesies inspired by the Grinch. One clip showed them enjoying a spa treatment together. Another featured them flashing middle fingers at the camera.

But one particular video sparked widespread attention for its suggestive content. Social media exploded with reactions. Some fans joked about it. Others criticized it.

What the fuck is Jazz Chisholm doing man pic.twitter.com/CvRzznZtAm

— Freddie🫡 (@PlayoffYankees) December 25, 2025

Chisholm did not stay quiet. When trolls attacked Santiago online with false claims about her past, he fired back.

“My fiancee has never done OnlyFans,” Chisholm wrote on X. “But maybe your mom did. Check on her real quick.”

He later posted a message acknowledging the chaos. “Yall be making me feel like I’m not a normal person even in my offseason. I can’t have fun on this app. I’m a normal person. I can troll too and still put in the work. That’s why I’m where I’m at. Words don’t affect me.”

By Friday afternoon, Chisholm announced his fiancee had banned him from X. “I guess I’ll see y’all in a month or so,” he wrote.

Who is Ahnalys Santiago?

Yankees star Jazz Chisholm Jr. announced his engagement to Ahnalys Santiago on Dec 7, 2025.
macdaddyahna@instagram

Santiago, 25, was born on August 13, 2000, in Plainfield, New Jersey. She is of Puerto Rican and Dominican descent.

Her music career began in 2019 with the release of her debut single “Run It.” The track crossed one million streams on Spotify and established her presence in the R&B scene. She has since released other songs including “Forever Sorry,” “Bed Head,” “Situationship” and “Ecstasy.”

NY Yankees star Jazz Chisholm explains that he knew about his Fiance Ahna Mac’s Ø/F and all the money she makes from “scamming men” on there goes right to his bank account 😮👀
pic.twitter.com/uuReoUZMsn

— Slime🐍 (@ItsKingSlime) December 27, 2025

But Santiago gained her widest fame through reality television. She joined the Zeus Network’s “Baddies East” in 2023. Her bold personality made her one of the most talked-about cast members. She later appeared on “Baddies Caribbean,” “Baddies Midwest” and “Baddies Africa.”

Her Instagram following has grown to over 1.5 million. She was named a brand ambassador for luxury fashion house Diesel earlier in 2025.

The couple kept their relationship private for most of the year. Santiago first hinted at it publicly by posting a photo from Yankee Stadium in October. On December 7, she shared photos of herself and Chisholm in a pool with a caption that foreshadowed the engagement.

“Da Parents,” she wrote then. “See y’all at our wedding next year.”

Chisholm delivered a historic season for the Yankees in 2025

The engagement caps a banner year for the Bahamian infielder. Chisholm put together the best season of his career despite missing the entire month of May with an oblique strain.

He finished 2025 with a .242 batting average, 31 home runs, 80 RBI and 31 stolen bases. The 31/31 campaign made him just the third player in Yankees history to record a 30/30 season. He joined Bobby Bonds (1975) and Alfonso Soriano (2002-03) in that exclusive club.

Fun fact: Jazz Chisholm hit more home runs in one playoff game than the entire Red Sox roster did in 3 whole playoff games pic.twitter.com/uYTN9rFDcy

— Evil Empire (@octoberstanton) December 26, 2025

Chisholm also set career highs in runs scored (75) and walks (58). His .813 OPS and 4.4 fWAR ranked among the best at his position in the American League.

The performance earned him his first career Silver Slugger Award. He beat out Brandon Lowe of the Rays and Jorge Polanco of the Mariners for the honor.

Chisholm credited the Yankees environment for his growth.

“The winning mentality, the winning atmosphere,” Chisholm said. “The way everybody from the front office to the training staff wants to win. It’s how I felt like I grew up playing baseball, and what I needed to be around to be even more successful.”

Contract uncertainty clouds his future in the Bronx

New York Yankees' Jazz Chisholm Jr. runs to the dugout during the eighth inning of a baseball game against the Baltimore Orioles, Sunday, Sept. 28, 2025, in New York.
AP Photo/Pamela Smith

The engagement news arrives during an uncertain time for Chisholm professionally. He enters 2026 in the final year of his contract. Free agency awaits after next season.

General manager Brian Cashman said at the Winter Meetings earlier this month that no extension talks have taken place. The Yankees appear “lukewarm” about committing long term.

“He’s above-average. He’s an All-Star second baseman, great defense, steals bags, power,” Cashman said. “All that stuff. He’s been a good get.”

Still, Cashman added that Chisholm is “currently part of the solution.”

“He’s somebody who’s made us better by getting him two deadlines ago, giving us athleticism,” the GM said.

Trade rumors have swirled. The Philadelphia Phillies have been mentioned as a potential destination. Yankees insider Bryan Hoch raised the possibility of dealing Chisholm before he walks for nothing in free agency.

Chisholm has expressed his desire to stay in New York. The organization has yet to reciprocate with a formal offer.

Personal happiness could fuel his 2026 campaign

Some fans believe the engagement could boost Chisholm’s production next season. A settled personal life often helps athletes perform at their peak.

Chisholm has flashed 40/40 potential. His combination of power and speed is rare in today’s game. Only three other players recorded at least 20 home runs and 30 stolen bases in 2025.

The stakes for 2026 could not be higher. Chisholm will be playing for his next contract. He will be playing to prove the Yankees should commit to him. And now he will be playing with a ring on his finger.

Santiago and Chisholm have not announced a wedding date beyond confirming it will happen next year.

One fan on social media summed up the sentiment perfectly. “Congrats, Jazz. My goat. 40/40 next year.”

For now, the baseball decisions can wait. The Northern Lights proposal made sure of that.

What do you think? Leave your comment below.

Tags: New York YankeesAhna MacAhnalys SantiagoBaddiesBrian CashmanChristmas proposalengagementFinlandFree agencyjazz chisholmMLBNorthern Lights
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Sara Molnick

Sara Molnick

A digital technocrat-turned-baseball buff, Sara is an ardent follower of the New York Yankees. Born and brought up in New York City, she is a regular to games since she was a kid. Despite working as media strategist, baseball is her first love. She has been covering baseball games in the city as well as MLB and MiLB games involving the Yankees, the Mets, and their minor affiliates as a freelancer for different web and media publications. She works as a lead author for the Yankees-centered PinstripesNation since its very inception.

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