#4. Howie Kendrick
Howie Kendrick won the NLCS MVP award in 2019. Unfortunately, this was obviously not while playing for the Philadelphia Phillies.
After an impressive nine year career with the Los Angeles Angels (which included an All-Star game selection in 2011) and a stop across town with the Dodgers, Kendrick was traded to the Phillies for Darin Ruf and Darnell Sweeney. A somewhat strange move at the time considering the Phillies were still rebuilding the shape of the roster, Kendrick did offer some short term help at a variety of different positions. Predominantly playing in the outfield, Kendrick also played some innings at both second and first base.
Kendrick played just 39 games for the Phillies in 2017 before the front office made a decision on his future in Philly. Seeing as he was batting an impressive .340 at the time, the Phillies felt they would be better off trading him while his value was at its highest. Shipping him off to DC in exchange for some cash and a prospect, it looked like a fairly standard “buy low sell high” maneuver.
Luckily for the Nationals (and not so luckily for the Phillies), Kendrick seemed to age like fine wine. Since being traded to Washington, Kendrick has batted an absurdly high average of .322. He’s also provided above average defense while acting as a very positive leader in a fairly young clubhouse.
While he’s been operating primarily as a bench bat/rotation type player, Kendrick’s value for the Nationals has not gone unnoticed. Obviously he was an important piece to the team’s championship run this past season, and despite being set to turn 37 next month, the Nationals opted to pay him over $6 million to keep him around for 2020.
The prospect the Phillies got in return for Kendrick never panned out and now the former Phillie has a shiny MVP trophy on his dresser. This one hurts, and the Phils only have themselves to blame.