Jenny Dell’s husband is Will Middlebrooks, a former Boston Red Sox third baseman who now covers the team as a broadcaster. They met at Red Sox spring training in 2012 and married on February 14, 2016. Middlebrooks was part of Boston’s 2013 World Series championship team and worked on the club’s television and radio broadcasts in 2026.
Dell covered Boston’s 2013 championship season for NESN. More than a decade later, Middlebrooks was back at the ballpark as an analyst, in a second career that began with a studio appearance Dell helped arrange.
Who Is Will Middlebrooks?
Boston drafted Middlebrooks out of high school in 2007. He made his major league debut for the Red Sox on May 2, 2012, and played parts of three seasons with Boston. Third base was his main position. He played 94 regular-season games for the Red Sox in 2013 and hit 17 home runs that year, including three in one game against Toronto in April. He also made Boston’s World Series roster that October.
After Boston, he played for the San Diego Padres, Milwaukee Brewers and Texas Rangers. His MLB player record lists 43 career home runs and 155 runs batted in. Boston was where he spent the most time in the majors, and it was the team he returned to cover when he joined NESN.
How Jenny Dell and Will Middlebrooks Met and When They Married
They first met in Fort Myers, Florida, during spring training in 2012. Dell had just joined NESN. In a joint interview with The Boston Globe, she recalled that a mutual friend had told her about Middlebrooks before her first visit to the clubhouse. His locker was her first stop. A couple of months later, Boston called him up, and both were working at Fenway Park that season.
Middlebrooks shared a photo of the two on New Year’s Eve 2013, making their relationship public. In July 2014, he proposed in Newport, Rhode Island. He had arranged for friends and family to be waiting at a nearby restaurant, where the couple celebrated after the proposal.
They married in Arizona on Valentine’s Day in 2016. At the time, Dell had moved from NESN to CBS Sports and Middlebrooks was preparing for spring training with Milwaukee. He reported to the Brewers two days after the ceremony.
How Jenny Dell Helped Will Move Into Broadcasting
Middlebrooks played his final major league game for Texas against Oakland on October 1, 2017. He went to spring training with the Philadelphia Phillies the following year and broke his leg in an exhibition game. He retired from professional baseball in January 2019 after trying to work his way back from that injury.
Middlebrooks was reluctant to go on television at first. In a 2022 interview with MLB, he recalled how Dell arranged a CBS Sports studio appearance for him. He said it took him a few weeks to get comfortable with the idea of talking about games he still wanted to be playing. Once he gave it a chance, he found he could put his years of baseball experience to work in the studio.
He joined NESN in 2022 as an analyst on the Red Sox pregame and postgame shows. Former Boston players Kevin Youkilis and Kevin Millar joined the network that season too, working games from the booth while Middlebrooks started in the studio. He told MLB that he wanted to explain why a play unfolded as it did, drawing on what he had seen and done as a player.
What Does Will Middlebrooks Do Now?
During the 2026 season, Middlebrooks covered the Red Sox on television for NESN and on radio for WEEI. In its 2026 broadcast announcement, NESN listed him and Millar as rotating game analysts. It also included Middlebrooks in the group providing analysis before and after games. For two June games against Texas, he worked in a booth staffed entirely by former Red Sox players. Lou Merloni called the action, while Middlebrooks and Jonathan Papelbon provided commentary.
On the radio side, he worked with play-by-play announcer Will Flemming. The two interviewed Jahmai Jones for WEEI after he homered in a September 2026 win over Tampa Bay.
Dell joined CBS Sports in 2014 as an NFL sideline reporter. She began covering college football for CBS Sports Network the following year and became the lead college football reporter for CBS in 2022. Her CBS Sports bio lists her on the network’s top college football crew alongside Brad Nessler and Charles Davis, including on Big Ten broadcasts. She also anchors coverage on CBS Sports HQ.