Last Updated: July 27, 2026
Former Boston Red Sox third baseman Will Middlebrooks built a solid MLB career before transitioning into broadcasting. Today many fans still search for details about the woman beside him. That woman is Jenny Dell, a sharp, Emmy-nominated sports reporter who has carved out her own impressive path in television. Together they form one of the more grounded power couples in sports media.
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How Will Middlebrooks and Jenny Dell Met
Their story began at Fenway Park. In late 2012, Jenny was working as a sideline reporter for NESN covering the Red Sox. Will was the young third baseman trying to establish himself in Boston. What started as professional interaction quickly turned personal. They began dating that same year, kept the relationship relatively low-key at first, and got engaged in July 2014.
On Valentine’s Day 2016 they married in a sunny Arizona ceremony. The timing felt fitting for a couple whose relationship had grown out of shared long hours at the ballpark and a mutual understanding of the demands of sports careers.
Jenny Dell’s Career Journey
Jenny Dell (full name Jennifer Sheryl Dell-Middlebrooks) was born July 26, 1986, in Connecticut. She attended the University of Massachusetts Amherst before launching into sports broadcasting. After her early NESN days, she moved to CBS Sports, where she has covered the NFL and, more prominently in recent years, become the lead college football reporter.
She has earned praise for her preparation, calm presence on camera, and ability to deliver clear sideline reports under pressure. Colleagues and viewers often note that she balances the high-energy world of live sports with a natural, conversational style. Will has publicly credited her with pushing him into television after his playing career ended due to injury, calling her decision to “throw him to the wolves” one of the best things that happened to him professionally.
Family Life and Their Two Daughters
Will and Jenny are parents to two daughters: Madison Dell Middlebrooks, born in October 2018, and Makenzie Grey Middlebrooks, born in December 2019. The couple has spoken openly about the challenges of building their family, including fertility treatments that eventually led to the arrival of their girls.
Today the family balances busy travel schedules with intentional time together. Jenny often shares warm glimpses of motherhood and partnership on social media, while Will has described his wife as “the gold standard” of what it means to be a mother, wife, friend, and reporter. Their daughters have grown up around both the baseball diamond and the broadcast booth, giving them a unique window into the sports world.
| Detail | Information |
|---|---|
| Full Name | Jennifer Sheryl Dell-Middlebrooks |
| Born | July 26, 1986 (age 40) |
| Profession | Lead college football reporter, CBS Sports |
| Marriage Date | February 14, 2016 |
| Children | Madison (2018), Makenzie (2019) |
| How They Met | NESN Red Sox coverage at Fenway Park (2012) |
| Current Roles | Jenny at CBS; Will as NESN Red Sox analyst |
What Makes Them a True Sports Media Power Couple
What stands out about Will and Jenny is how complementary their careers remain. She works national college football and big events; he focuses on Red Sox studio and game analysis for NESN while also contributing to CBS. They understand each other’s travel, pressure, and public scrutiny. That shared experience has helped them build a partnership that feels both ambitious and rooted in real life.
They have reflected in recent interviews that their relationship was never just a fleeting clubhouse romance. A decade of marriage and two children later, they still talk about the early days at Fenway with affection and a sense of perspective. Fans appreciate the authenticity—neither one overshadows the other, and both continue to grow in their respective roles.
Conclusion
Will Middlebrooks wife, Jenny Dell, is far more than a supporting figure in his story. She is an accomplished broadcaster in her own right, a dedicated mother, and a steady partner who helped shape the next chapter of his career. Their journey from Fenway sidelines to a shared life in sports media offers a refreshing example of two professionals who found lasting connection in a high-pressure industry. As both continue to work in the game they love, their family remains the clear center of it all.