The high school multi-sport star who traded a college dream for baseball
In short: Will Middlebrooks was a standout quarterback and punter who preferred football over baseball. Yet, the lure of the MLB draft forced a pivot that redefined his career. From bypassing a full scholarship at Texas A&M to becoming a Red Sox sensation, his journey is a study in athletic transition.
Middlebrooks was a versatile athlete at Liberty-Eylau High School in Texarkana, Texas, where he excelled as a quarterback, placekicker, and punter. He even earned All-State honors as a punter. In fact, Middlebrooks admitted that he actually preferred football until his junior year, when the reality of being selected in the Major League Baseball draft became tangible. His initial trajectory was defined by internal struggle; despite pledging a full scholarship for football and baseball at Texas A&M University during late 2006, he eventually decided to withdraw.
The decision had immediate financial and developmental consequences. Drafted in the fifth round of the 2007 MLB draft by the Boston Red Sox, Middlebrooks received a $925,000 signing bonus. However, because of his heavy involvement in football, he was considered developmentally behind other minor league players initially. To accommodate his physical growth—increasing from 190 pounds to 210 pounds—the Red Sox converted him from his original position of shortstop to third base. This transition eventually paid off when he debuted on May 2, 2012, and quickly became a power hitter for Boston.
Middlebrooks' career was marked by high-ceiling potential and physical setbacks. He set a franchise record for the most RBIs in a first 41 games (34) since 1949–50, but struggled with injuries, including a broken hand and a strained calf. Following periods with the Rangers, Brewers, and Padres, a singular milestone occurred on 6 September 2017: he became the initial athlete in more than a century to record pinch-hit triples during both halves of a doubleheader. Today, he translates that experience into broadcasting for the Boston Red Sox.
His personal life also mirrored his professional shifts. After a high-profile engagement ended in 2012, he began dating Jenny Dell, a reporter for NESN. The couple eventually married in 2016 and navigated significant personal challenges, including fertility treatments to have their two daughters. His story highlights the grueling nature of professional sports—where physical evolution and strategic pivots are as vital as raw talent.
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