Yankees GM Cashman’s daughter Gracie gets engaged to Cubs’ fan, plans Irish wedding

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Gracie Cashman, host of YES Network’s The Story of My Number and daughter of Yankees General Manager Brian Cashman, has announced her engagement to Brian Stute. The news broke Monday through a series of photos shared on her Instagram account.

The proposal reportedly took place on a theater stage adorned with rose petals and floral arrangements, creating a dramatic and romantic setting. Images from the event showed Cashman and Stute celebrating alongside family and friends, including her father, who appeared visibly joyful. In one photograph, Stute kissed Cashman on the cheek as she displayed her engagement ring, surrounded by loved ones.

The engagement news comes shortly after the Yankees’ World Series loss to the Dodgers on October 30, providing a bright moment for the Cashman family. Social media posts also included lighthearted details, such as a photo of Cashman holding a bottle of Fireball whiskey with an engagement announcement.

While the exact location of the proposal hasn’t been disclosed, a Chicago-based photographer is credited for capturing the event. Cashman, who splits her time between Chicago and New York for professional reasons, is reportedly planning a move to New York with Stute to be closer to family and career opportunities.

Stute, a Cubs fan, has received approval from Brian Cashman despite his team allegiance. In a previous interview, Cashman remarked that Stute’s fandom offered a refreshing perspective, avoiding any starstruck moments—except for one memorable occasion during a surprise birthday party at Fenway Park.

“I actually think it works out a little bit better that way, because he doesn’t get super starry-eyed [around my dad],” the Yankees GM’s daughter said. “The one time he did a little was when we surprised my dad for his birthday and the team was playing in Boston.”

Gracie Cashman reveals about her engagement

Gracie Cashman, daughter of Yankees General Manager Brian Cashman, shared details of her recent engagement to Brian Stute in an exclusive interview with Us Weekly. The 26-year-old revealed that the proposal took place on Sunday, November 17, at a Chicago theater, with family members secretly watching from the opera boxes.

Stute carefully planned the surprise, convincing Cashman they were visiting a bakery to pick up a birthday cake for his sister as part of a family celebration. Instead, the couple arrived at an unfamiliar theater. Once inside the empty venue, Stute led Cashman to the stage, where he proposed in a setting adorned with sentimental touches. 

Cashman explained the significance of the location, as it tied back to their time at St. Luke’s School in New Canaan, Connecticut, where they met. The couple’s relationship began during a high school production of Legally Blonde: The Musical, in which they played Elle and Warner. Their romance started during her junior year and his senior year but was briefly paused during their college years before rekindling after both moved to Chicago.

“We met in high school doing Legally Blonde: The Musical, which is why he proposed on a stage,” Gracie told. “I was playing Elle and he was playing Warner. We started dating my junior year of high school, his senior year. We did break up towards the end of college and then we got back together when we both moved to Chicago. We weren’t very good at being broken up anyway. We were pretty consistently talking.

“I knew his family was in town for his little sister’s birthday,” Gracie said. “He told me we were going to do brunch and then dinner. I thought we had this weekend with his family, so I didn’t have any plans. He said we had to stop at a bakery to pick up a birthday cake before brunch. On the way there, we did not go to a bakery, we went to this theater that I had never been to.”

Even during their time apart, Cashman noted, the pair stayed in touch, maintaining a bond that eventually led them back to each other. The theater proposal, she added, symbolized not just their shared past but the journey that brought them to this new chapter.

Gracie Cashman’s engagement to Brian Stute was celebrated with a heartfelt family gathering, as both sides joined the couple for post-proposal festivities. According to sources, Gracie’s parents, who are divorced, along with her brother Teddy, emerged after the proposal to capture the moment in photos. The celebration continued aboard a classic Chicago trolley, complete with Fireball whiskey shots, leading to playful discussions about morning cocktails among attendees.

The engagement ring, steeped in sentimental value, reportedly belonged to Gracie’s late maternal grandmother. Gracie’s mother entrusted the heirloom ring to Stute for the proposal, adding a personal touch to the occasion.

As for wedding plans, Gracie, known for hosting The Story of My Number on The Gotham Sports App, has urged friends and family for patient as details unfold. Sources say she is leaning toward a winter wedding, likely two years out, to ensure ample time for planning.

An international destination is under consideration, with Ireland emerging as a frontrunner due to the family’s deep Irish heritage. Reports note that Gracie’s father, Yankees GM Brian Cashman, is of full Irish descent, while her mother is predominantly Irish. Gracie has acknowledged their Irish Catholic roots as a meaningful influence in the decision-making process, though the couple remains open to other possibilities for their special day.

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