Boston Red Sox

Rusney Castillo is a reminder of one of the dumbest things the Red Sox have ever done

Would Jon Lester be pitching in Boston if the Red Sox had avoided Rusney Castillo?

Former Red Sox pitcher Jon Lester is 9-3 with a 2.06 ERA during his second season with the Chicago Cubs. USA Today Sports

COMMENTARY

Not that Red Sox fans necessarily need the periodical status update, but old pal Jon Lester won his ninth game of the season over the weekend in Chicago, a six-inning, three-run performance against the Pittsburgh Pirates that actually ranks as his second-weakest outing of the year for the Cubs.

Meanwhile, in somewhat related news, Boston essentially announced that it was giving up on Rusney Castillo, reportedly placing the $72.5 million bust on waivers Sunday.

He is, perhaps, the most egregious mistake in franchise history.

It truly says something about a particular Red Sox regime when the debate over the worst contract decisions made by a century-plus old franchise narrows itself down to a half-decade of choices. Was Carl Crawford the worst free-agent signing in Red Sox history? Was it Pablo Sandoval? Hanley Ramirez? Or Rusney Castillo?

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That’s a list of names that, by comparison, has the likes of Julio Lugo in the upper echelon of sound judgements.

For all the good Ben Cherington did during his time in Boston grooming a farm system into one of the stronger ladders in Major League Baseball, there’s little argument that he was the worst general manager in at least a generation. The fact that he earned himself a World Series ring will go down as an anomalous highlight in his Boston sports profile.

He also played the role of the goat, and we don’t mean G.O.A.T.

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No, the blunders that led to three last-place finishes over the past four years were clearly a group effort, made possible by team philosophies that seemingly calibrated themselves depending on the direction of the breeze in the Back Bay. This is why you can find Panda chapeaus on discount and wonder why the dynamic abilities of Crawford never really delivered those boffo TV ratings.

But even in a season during which the Red Sox, buoyed by a fascinating, young core of players, have found themselves back in contention — partly in thanks to eschewing some of the phantom team-building rules that had sunk them the last two years — they can’t escape their expensive blunders of the recent past. This time, Magic Johnson and the Los Angeles Dodgers aren’t coming to bail them out.

Thus, barring the unlikelihood that anyone else is foolish enough to claim him, they will pay the 28-year-old Castillo another $32.5 million over the next three seasons to 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 (a record for an amateur free agent) for anything of worth.

Red Sox owner John Henry would have found a better return on his investment if he sank $72.5 million into Zune stock.

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Or, better yet, Jon Lester.

It was a little more than three weeks after the Red Sox traded Lester to the Oakland A’s for Yoenis Cespedes in July 2014 that the team announced its agreement with Castillo, the result of a bidding war over a player from Cuba who brought great potential. Over his first 99 MLB games, Castillo’s potential has not exactly translated: He hit all of .262 with seven home runs and a .679 OPS.

In December 2014, Cespedes went to the Detroit Tigers for Rick Porcello, who has won 17 games over two years as a member of the Red Sox, with an $82.5 million deal attached. Lester, of course, signed a six-year, $155 million contract with Theo Epstein and the Cubs that same month. He has gone 20-15 for Chicago over the past two seasons with a 2.94 ERA. The Red Sox came up short in pursuing their guy as a free agent — managing to offer “only” $135 million over six years — amid Henry’s public uneasiness about dedicating large amounts to a pitcher entering his 30’s.

It was “the best we could do,” according to Cherington.

No. It wasn’t.

One only has to fast-forward to last winter when the Red Sox set the market with a $217 million deal for David Price, who turns 31 at the end of August, to find a retort to that statement. Unfortunately, there was no mantra, however malleable, that kept the team from throwing $72.5 million to the international scouting department for an unproven commodity in lieu of bringing back a pitcher who had been a staff cornerstone.

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Of course, if Lester were still here, Price probably would have wound up elsewhere during his free-agent process. Then again, if Cherington and company hadn’t somehow believed that $167.5 million combined for Sandoval and Castillo were solid decisions, perhaps the Red Sox might have also had the resources to dedicate funds toward avenues worthy of pursuit.

What an incompetent stretch of decisions.

There is understandable fear of being tied down to the next Josh Beckett when it comes to aging, high-priced pitching, but it remains a questionable theory to throw similar money, albeit at shorter years, at a guy like Porcello simply because the man is four or five years younger than the ace on the market with a lengthy resume.

The Red Sox are still looking for another pitcher to slot behind their ace, whether you consider that to be Price or the Magic Pixie who accompanies Steven Wright to the mound every fifth day.

If the Red Sox and Cubs do, somehow, meet in the World Series, we could very well see Lester and Price going in Game 1, a pair of pitchers that represent the best in the game, not to mention two symbols of just how distorted and mangled the day-to-day philosophies on Yawkey Way have been.

Until then, there are probably lots of good seats to watch Rusney from at McCoy.

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