Will Middlebrooks
A power-hitting third baseman whose explosive debut season with the Red Sox was a bright spot before injuries reshaped his career path.
Born 1988 (age 38)·American baseball player·Birthday: September 9·Millennials
Biography
Will Middlebrooks arrived in Boston with the force of a Texas swing, a fifth-round draft pick who quickly announced himself as a potential cornerstone. In 2012, his rookie year, he seemed to be living a dream, launching 15 home runs in just 75 games and briefly making fans forget the injured Kevin Youkilis. His raw power and defensive agility at the hot corner made him an instant Fenway favorite. However, the trajectory of a sports career is rarely linear. A series of fractures and other injuries began to stall his momentum, limiting his playing time and consistency. After being traded to San Diego in 2014, he embarked on a journeyman phase with stops in Milwaukee and Texas, never quite recapturing that initial explosive form. His graceful pivot into broadcasting, where he now provides sharp, experienced analysis for the Red Sox radio and TV networks, has made him a familiar and insightful voice for a new generation of Boston fans.
Millennials
1981–1996
The first digital natives. Grew up with the internet, came of age during 9/11 and the 2008 crash. Highly educated, deeply indebted, slower to marry and buy houses. Redefined work, identity, and what it means to be an adult.
Will was born in 1988, placing them squarely in the Millennials. The events that shaped this generation — the internet revolution, 9/11, and the 2008 financial crisis — shaped the world they entered and the choices available to them.
#1 When Will Was Born
The biggest hits of 1988
#1 Movie
Rain Man
Best Picture
Rain Man
#1 TV Show
The Cosby Show
Will's Life & Times
The world at every milestone
1988Born
Pan Am Flight 103 bombed over Lockerbie
Gas: $0.90/galHome: $74,800Min wage: $3.35/hrPresident: Ronald Reagan"Faith" — George MichaelBest Picture: Rain Man
1993Started school
European Union officially established
Gas: $1.11/galHome: $86,600Min wage: $4.25/hrPresident: Bill Clinton"I Will Always Love You" — Whitney HoustonBest Picture: Schindler's List
2001Became a teenager
September 11 attacks transform the world
Gas: $1.46/galHome: $126,400Min wage: $5.15/hrPresident: George W. Bush"Hanging by a Moment" — LifehouseBest Picture: A Beautiful Mind
2004Could drive
Indian Ocean tsunami kills over 230,000
Gas: $1.88/galHome: $157,300Min wage: $5.15/hrPresident: George W. Bush"Yeah!" — UsherBest Picture: Million Dollar Baby
2006Could vote
Twitter launches; Pluto reclassified as dwarf planet
Gas: $2.59/galHome: $174,700Min wage: $5.15/hrPresident: George W. Bush"Bad Day" — Daniel PowterBest Picture: The Departed
2009Turned 21
Michael Jackson dies; Bitcoin created
Gas: $2.35/galHome: $148,500Min wage: $7.25/hrPresident: Barack Obama"Boom Boom Pow" — The Black Eyed PeasBest Picture: The Hurt Locker
2018Turned 30
Royal wedding of Harry and Meghan; Parkland shooting
Gas: $2.72/galHome: $211,800Min wage: $7.25/hrPresident: Donald Trump"God's Plan" — DrakeBest Picture: Green Book
2026Age 38 today
Gas: $3.91/galPresident: Donald Trump
Key Achievements
- Hit 15 home runs in his first 75 MLB games in 2012, setting a torrid pace for a Red Sox rookie.
- Was a key contributor during the Boston Red Sox's 2013 World Series championship season, appearing in 94 games.
- Hit for the cycle in a minor league game for the Triple-A Pawtucket Red Sox in 2014.
Did You Know?
He was drafted as a shortstop but was converted to a third baseman in the Red Sox minor league system.
He married fellow professional athlete Jenny Dell, a sportscaster and former New England Sports Network reporter.
He provided color commentary for an ESPN Radio broadcast of a 2024 American League Wild Card series.
“You have to produce when you get the chance, or the chance goes to someone else.”
