Mastermind /// J. Olson

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ESPN

DALLAS BENNETT IS ENGAGED!
The Chicago Cubs outfielder's longtime boyfriend popped the question in Texas

March 21, 2023

Chicago Cubs outfielder Dallas Bennett got engaged to her longtime boyfriend, Savannah Bananas infielder and MLB Ambassador Jackson Olson while visiting him during the Bananas series in Sugarland, Texas. Bennett, 26, and Olson, 25, have been together since 2015 and there has been nothing but support from both sides. Bennett was drafted in the second round of the 2015 MLB Draft by the Los Angeles Dodgers and Olson was by her side. "He's been in my corner since high school," says Bennett. "He's my biggest fan and I'm his." Olson was named an MLB Ambassador in 2021 and signed with the Savannah Bananas in 2022. "I've had so many incredible opportunities since I finished college and Dallas has been by my side since high school," says Olson. "We're each other's biggest fans."

"Eight years is a long time and I'm incredibly happy for them," says Chicago Cubs outfielder Cody Bellinger. "Jackson makes Dallas extremely happy." Bennett and Bellinger were teammates on the Dodgers and both elected free agency following the 2022 season. Adds Milwaukee Brewers outfielder Christian Yelich, "I've known Dallas since 2017 and I knew Jackson was perfect for her when I met him in 2019 at the All-Star game. He cares about her and it shows."

While he didn't know about Olson's relationship with Bennett, Savannah Banana catcher and co-captain Bill Leroy says, "We're all happy for Jackson. We were shocked to find out he and Dallas were together, especially given her reputation." Adds former Seattle Mariners Minor Leaguer Eric Jones Jr., "Last summer, I noticed that he was always checking on the stats for the Dodgers and didn't think much of it. I started to suspect after seeing a bunch of posts from the Dodgers on his Instagram story and I thought 'Okay, maybe he knows someone on the team with him being an MLB Ambassador.'"

New York Yankees outfielder Aaron Judge says, "You can tell how much they love each other. Dallas told me about her relationship when we were at the 2018 All-Star game together and then I met Jackson at the 2021 All-Star game. I instantly knew they were perfect for each other." Los Angeles Dodgers outfielder Mookie Betts adds, "I'm happy for them. Dallas introduced me to Jackson back in February of 2020 and I didn't know much about either of them but I knew they would last."

Chicago Cubs manager David Ross says, "Dallas has been an incredible addition to the team and she's happiest when she's on the field or talking about her relationship with Jackson. You can tell how proud she is of him and I'm happy for them." Cubs infielder Dansby Swanson adds, "I haven't known Dallas for very long but you can tell she's extremely happy with Jackson. You can see her eyes light up when she talks about him."

While the couple have posted each other on social media for years, neither party outright stated that they were together. "We really only wanted family and close high school friends to know we were together," says Bennett. "We did use a lot of phrases that made it seem like we were together but we didn't think much of it at the time. Like, Jackson said 'my girl' in his post when I was drafted. We didn't think anything of it and nobody really asked about it." Adds Olson, "The 'my girl' caption was a force of habit. I've always called Dallas my girl, even before we were dating. Our friends and family thought we were based on how we interacted with each other."

"I'm super happy for Dallas," says Dodgers infielder Freddie Freeman. "And I'm glad they could keep their relationship private for as long as they did. Most couples aren't that lucky. Dallas is very private; when asked about her love life, she was very vague. She said she was in a relationship but never mentioned who it was or how long they'd been together."