2007
This starting point is a train wreck, but not one of epic proportions. As will be noted with prospects they sometimes bring value via trade.
Nick Hagadone was drafted out of the University of Washington. The left-hander physically resembled Jon Lester and the comparison ended when Hagadone took the hill. The Red Sox packaged Hagadone with Justin Masterson and Bryan Price and shipped them to Cleveland for Victor Martinez.
In five seasons with the Indians, Hagadone appeared in 143 games – all in relief – and posted a 4.72 ERA. Hagadone became a free agent and signed with the Brewers for the 2016 season. Hagadone was MOA for 2016 and signed with the Seattle organization for 2017 where he pitched for Tacoma (AAA) before being released.
Ryan Dent made it as far as Pawtucket (AAA) in his eight seasons with the Red Sox organization. The right-hand hitting Dent has played all over the diamond except catcher. Dent won a game for Portland (AA) in 2013 tossing two shutout frames. Maybe he should have stuck with that?
Dent moved on to the Cubs organization where he was released in the spring of 2016 and finished that season and the next in independent ball. In his minor league career, Dent has a .235 average. So, the result is simple – Dent has failed.
There are often nuggets in each draft where a team may get lucky or a player matures. For 2007 that player was Anthony Rizzo. The Red Sox used Rizzo as a trade chip for Adrian Gonzalez and later Rizzo moved to the Cubs. Rizzo is a three-time All-Star.