Daughter of Yankees GM, Gracie Cashman, Details Her Surprise Engagement

Gracie Cashman and Brian Stute.

Gracie Cashman, daughter of New York Yankees GM Brian Cashman, was surprised by a marriage proposal that truly knocked it out of the park. 

Gracie, 26, said “yes” when boyfriend Brian Stute popped the question on the middle of a stage in Chicago on Sunday, November 17, with the couple’s respective families hiding in the theater’s opera boxes. 

Now, in an exclusive interview with Us Weekly, Gracie is explaining how her newly-minted fiancé pulled off the big ruse. 

“I knew his family was in town for his little sister’s birthday,” she 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.”

Celebrity Engagements of 2024: See Which Stars Got Engaged This Year

Gracie continued, “When we walked in, it was completely empty. The stage and everything. He took me on the stage, got on one knee and asked me to marry him.”

The proposal’s location was chosen by Stute for a very specific reason, harkening back to their days together at St. Luke’s School in New Canaan, Connecticut. 

“We met in high school doing Legally Blonde: The Musical, which is why he proposed on a stage,” Gracie explained. “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.”

She added, “We weren’t very good at being broken up anyway. We were pretty consistently talking.”

After the proposal, both families — including Gracie’s parents, who are divorced, and brother, Teddy — emerged and took pictures with the newly-engaged couple before the whole crew loaded into a trolley — “a very Chicago thing to do,” Gracie joked — that was loaded with Fireball shooters.

“We were laughing,” Gracie remembered, “because all of us on the trolley were like, ‘Oh my god, it’s 11 a.m., but should we do the Fireball shots? Definitely.’”

Stute proposed with the ring of Gracie’s grandmother, the late mother of Gracie’s mom, Mary. 

“She died when I was 2,” Gracie said. “My mom had her engagement ring and she let my boyfriend use it.”

‘The Summer I Turned Pretty’ Star Gavin Casalegno Is Married

Of course, now the wedding planning begins. But Gracie — who hosts The Story of My Number, available on The Gotham Sports App — urged her friends and family to exercise some patience while she plots out the big day. 

“I think we’re going to have to pick a date pretty far in the future,” Gracie explained. “I think we’ll pick a date in the winter. I’ve always wanted a winter wedding. I think two years from now in the winter will be enough time for people to figure it out.”

As for a location, Gracie hinted she’s “always wanted to get married abroad” and has her sights set on one country in particular. 

“I’ve always wanted to do Ireland,” she said. “I haven’t been to Ireland in years, but my Dad is 100 percent Irish. My mom is over 50% Irish. So, I’m over 75% Irish. We’re a pretty traditional Irish Catholic family in a lot of ways. I would like to do it there, but obviously we’ll see.”