The Boston Red Sox have had trouble in the past with horrible free agent signings, but the signing of Rusney Castillo might be the one that many Sox fans of this generation will remember the most.

The outfielder broke out as a highly touted Cuban prospect, and the Red Sox outbid teams like the New York Yankees and Los Angeles Dodgers to sign Castillo. High expectations circulated the 27-year-old rookie and, with the recent departure of Jacoby Ellsbury, he was expected to fill big shoes.

There’s a list of names that, by comparison, makes Sox fans shiver and turn away at the mere thought. Names like Carl Crawford, Julio Lugo, and Pablo Sandoval all headline the list of bad decisions in the last decade. It is now time to say that Rusney Castillo is part of that list.

For all the good Ben Cherington did during his time in Boston, in building a farm system into one of the leagues best in the league, there’s little argument that he is one of the worst general managers in, at least, a generation. By being the notorious GM who made questionable moves, the fact that Cherington earned himself a World Series ring will go down as one of the biggest mysteries in his Sox career.

However, despite the anomaly that was Cherington during his Red Sox career, Boston has built yet another championship caliber team in his wake. The name Dombrowksi is now synonymous with a winning attitude. Only a select few times in a Dave Dombrowski era has a team acquired a player who turned into a league-known bust. He now has to deal with the mess that Cherington made, in the money pit of Rusney Castillo.

The tricky deal regarding Rusney is the unlikelihood that anyone else is foolish enough to claim him, and it’s understandably so. They would have to pay the now 29-year-old Castillo another $32.5 million over three years, since Castillo cleared waivers as a member of the Red Sox and is no longer on the forty-man roster. For the next three seasons, he will play for Pawtucket, a Triple-A city where he’s already failed to create any argument that the Red Sox dedicated nearly twice that amount of money, which is a record for an amateur free agent, for anything of worth. In short, Rusney Castillo has been a big waste of money, and he is a waste of budget in Pawtucket.

How can we fix this problem? In my opinion, there is no solution to Rusney.

Now with the breakout of Mookie Betts as a MVP caliber outfielder and Jackie Bradley Jr.’s rise, Castillo has no control over center or right field. With the short sample of Andrew Benintendi, one can say that Castillo will no longer play left field ever again. Even if Benintendi was hurt, the dependability of Chris Young and Brock Holt and the experiment of Blake Swihart makes it even less likely. He has no place on an active roster. After spending time in Triple-A, Castillo has shown little to no progress in becoming a better hitter – only hitting .263 in 103 games. He’s joined the likes of Allen Craig as now a career Triple-A player, seeing the occasional call up to platoon for an injured player.

It’s unsure to predict what is next for Rusney; however, from what has emerged over the last season in the Red Sox outfield, the future looks dire. Unless he makes a substantial turnaround, there is no chance we see him again in a Red Sox uniform. Hopefully, he proves me wrong.