Does Ben Cherington Deserve More Time?

On October 25, 2011, Ben Cherington took the big chair in the Red Sox front office. Since then, things have been … eventful. Cherington was on the job in 2012, which was an unmitigated tire fire under new manager Bobby Valentine. There was beer. There was chicken. There was massive underperformance, and situations that made Theo Epstein’s gorilla suit look staid.

Cherington was also at the helm during 2013, which ended with a parade, a nice new World Series trophy for the ol’ living room, and far too many beards [editor’s note: nonsense]. 2014 was supposed to be more of the same, but it turned out to be less of something different. And though 2015 was supposed to be a return to championship form, perhaps it was a regression to a different sort of mean. Suppose, for just a moment, that the Boston Red Sox of the last four seasons aren’t a good team that’s fallen on bad times with one shining breakthrough. Imagine that they’re a bad team that did well for a single season.

If that were the case — and I’m not saying that it is — would you think that Ben Cherington should lose his job at the close of the 2015 season?

It’s a tough question, and one without an easy answer. You fire Cherington if you think he’s done a bad job, but we don’t even know how to tell whether or not a GM does a bad job. Do you look at wins? Wins are great, but there’s luck involved in any team’s win-loss record. If you try to strip out luck from the Cherington years, you could use Pythagorean Win-Loss records for these Red Sox teams, but that doesn’t change much. That terrible 2012 team, according to Baseball-Reference, won only 69 games, but their run scoring and prevention was that of a 74-win team. The 2013 team “underachieved” as well, scoring like a 100-win team instead of the 97 wins they posted en route to greatness. In 2014 and 2015, the team over- and under-achieved by a single win, respectively.

So if we use wins, Cherington’s teams deserved about eight additional wins that the team never achieved. That’s great, I guess, but it’s hardly evidence that the team was a winning team over his tenure. It simply doesn’t move the needle very much at all.

As of Monday, August 10, the Red Sox had won 50 games in 2015, and 287 wins over Cherington’s tenure. That’s great, I suppose, unless you consider that Cherington’s teams have also lost 311 games. Believe it or not, that is a .480 winning percentage, and that’s one of the worst runs a Boston GM has had in the team’s history.

I went back and ran the numbers for each of Boston’s GMs and co-GMs — that runs back to 1933 — and only three other tenures had a negative winning percentage, with Cherington’s being the fourth. Amazingly, all three previous tenures occurred back-to-back-to-back, from 1959 through 1965. Bucky Harris had a .455 winning percentage between 1959 and 1960. After that, Pinky Higgins and Dick O’Connell combined to lead the team to a .472 winning percentage over the ‘61 and ‘62 seasons. Then, when Higgins had the reigns all to himself over the next three years, the team struggled to a .433 winning percentage before — mercifully — Higgins was replaced with Dick O’Connell permanently.

As of Monday, August 10, the Red Sox had won 50 games in 2015, and 287 wins over Cherington’s tenure. That’s great, I suppose, unless you consider that Cherington’s teams have also lost 311 games. Believe it or not, that is a .480 winning percentage, and that’s one of the worst runs a Boston GM has had in the team’s history.

Here’s another weird GM win-loss factoid for you: Cherington also had the second-worst win-loss record in his inaugural year of any Sox GM. Only Eddie Collins (1933) had a worst first year … and that was the first year anyone was officially a GM of the Red Sox.

And here’s your last win-loss fact about the Cherington era: if the Sox carry this winning percentage that they currently have now — look to the right of your screen, and it’ll probably look a little like .446 — that would likely be the third-worst final season of any GM’s tenure in Boston, were it to be Cherington’s last at the helm. Only Bucky Harris and Pinky Higgins version 2.0 had a rougher final season than what Cherington is experiencing now.

All that I’m getting at here is that Cherington’s tenure as Sox GM has been, in terms of wins and losses, almost historically bad — at least in the context of previous Red Sox GMs. Of course, that’s only one part of the equation making up what makes a successful general manager, but it may be the most visible one.

Here’s another way of looking at the Cherington “problem” … if one exists. Jeff Sullivan at FanGraphs offered a tough question for any fan: would you rather have experienced the 2012-2015 seasons as a Red Sox fan, or the 2011-2014 seasons as a Tigers fan? Having lived in the Detroit area since the ‘13 season, and having lived in Boston during the Red Sox run in 2007, I can pretty definitively say the general population would take a year of World Series bliss over four years of sterling, strident competency. But maybe that’s the difference between Boston fans rabid for the navy and red, versus Detroit fans who are no less engaged, but perhaps not whipped into the same frenzy as their Bostonian brethren.

But the question in our minds isn’t which we’d rather have as a fan … it’s which one is more desirable from a team standpoint? Would you rather have three disappointing, losing seasons surrounding a trip to the top of the mountain, or would you rather build a tremendous regular-season team that featured a World Series appearance, two ALCS drop-outs, and one year eliminated in the division series?

It’s a false dichotomy, of course. If Dave Dombrowski were in charge of the Red Sox (and I guess he might be soon enough), that doesn’t mean that the Sox would’ve been the Tigers, or vice versa. Each team has wrinkles and personnel and events that supersede even the high authority of the general manager.

My guess is that financially, you’d rather have the consistent presence in the playoffs, as the gate revenues, the TV revenues, all the cool things that come with winning — they all add to your bottom line. Spiritually, though it’s deflating to be a losing team three times out of four, you probably still go with the Sox because flags fly forever.

But, in my heart of hearts, I bet that if I’m a general manager, I would take the consistent victories over four full seasons over one year of up, and three of down. Consistency means that your process is working over the long haul, that you’re the casino, not the kid at the craps table.

Coming into the offseason, the process actually looked pretty good for the Sox. The acquisitions of Rick Porcello, Pablo Sandoval and Hanley Ramirez seemed expensive, but sound bets on guys whose past performance — with all other indicators included — predicted future stability, if not success. Instead, the team has gotten nothing from their large investments.

And yet … I’ve said this before: the future looks a bit bright in Boston, or at least in Pawtucket, Portland, Lowell, Salem, Greenville, etc. The Red Sox have graduated, or will graduate, players from one of the top farm systems in all of baseball. Though Mookie Betts and Xander Bogaerts are Epstein guys, and not Cherington guys, Eduardo Rodriguez, Rafael Devers, Brian Johnson … those are Cherington guys. Brock Holt and Rusney Castillo are Cherington guys. Andrew Benintendi looks like the next Schwarber/Conforto quick-rising college bat.

The 2015 Red Sox are underperforming, to be sure. Their offense was supposed to lift a sketchy pitching staff to great heights, and instead everything seems to be falling apart. But what position is the team in going forward? That’s the question we have to use to judge Ben Cherington’s tenure as a general manager. If the team looks like it could be successful over the next three years, then perhaps three down seasons were worth it. If the team could vacillate between high potential and low performance again over the next few years, then it may be safe to say that he wasn’t — or isn’t — the right man for the job.

It’s tough to measure process, as compared to results, but Cherington typically gets pretty good reviews for his methods. The results? Well, you can’t discount that magic 2013, but other than that, they haven’t been that good. Perhaps it’s too soon to offer a true referendum on Cherington’s overall performance. In my opinion, it simply hasn’t been enough time to say decisively whether or not he deserves to be cast aside in favor of the new, hot GM candidate. I’d say give Cherington one more year to see if process wins out. If it doesn’t, though, he could go down in history as one of the least successful GMs in Red Sox history, World Series or no.

Photo by Bob DeChiara/USA Today Sports Images