Brian Roberts- 4 year/$40 million
A fantastic baseball player and now an insightful broadcaster for the Orioles on MASN, Roberts’ four-year/$40 million extension at age 32 proved to be another unfortunate financial decision in Birdland.
Through his first nine seasons in Baltimore, Roberts was an on-base machine, recording 50+ doubles three different times, double-digit home runs four times, and swiping 249 bags, including a league-leading 50 in 2007. He was a fan-favorite at Camden Yards with his electric play on the field and beaming personality. Personally, he was someone I studied and looked up to during my high school days as I debated whether or not to continue playing the game.
Sadly, injuries decimated Roberts’ career after his extension, appearing in just 59 games in 2010, 39 in 2011, 17 in 2012, and 77 in 2013. To his credit, Roberts always came back and tried to contribute, but the human body can only take so much.
Roberts gave it one last go in 2014, signing with the Yankees for $2 million. He hit .237 with 25 extra-base hits and 21 RBI in 91 games before calling it a career. Don’t worry, Brian, there’s no hard feelings for trying to give it a go in New York.