In an exercise of reflection, chief baseball officer Chaim Bloom was asked to list one thing he regrets and one thing he’s most proud of in his few years atop the Red Sox front office.
The executive paused for a while.
“There’s a ton of things in both categories,” Bloom said in a phone conversation this week. “You could ask me in the last week, the last month, the last three years.”
Pick one, he was encouraged.
“I think ultimately you could put some of the results of this in both categories, but I’ll give you something that’s a double-edged sword, but might answer both halves of your question without singling out a specific instance in each case,” Bloom said. “I think we haven’t been afraid to do things that were controversial or might not make sense to people at first glance when we believed they were right.”
The idea is that Bloom’s greatest regret and greatest achievement were both born out of the same confidence (stubbornness?) to do what he and his team felt was best, regardless of what the fans wanted, what the media highlighted, or what anybody else had to say.
The Red Sox Way is the Only Way, and changes won’t be made because of what people outside their walls think, say, or do.
That brings us to the 2023 Red Sox, who will begin spring training this week as a team expected by many to finish in last place for the second straight season.
But the front office continues to boast the idea that the Red Sox are in great shape, much to the dismay of some frustrated fans who, just a few weeks ago, wouldn’t let Bloom get three sentences out before relentlessly booing him at Winter Weekend.
Taking flak isn’t new for leaders in the Red Sox front office. And while he might get heckled for it, Bloom’s confidence in the team’s direction, regardless of what the general public thinks, paints the picture of an executive who isn’t afraid of making decisions that aren’t popular.
“When you do something that may be controversial and it doesn’t work out, you’re going to take a lot more flak for that than if you did something people were expecting and it didn’t work out,” Bloom said.
Is that actually true? Over the last 12 years, a handful of instances stand out
Some obvious moves: acquiring Adrian Gonzalez and Carl Crawford in 2011. They were two proven All-Stars that filled positions of need and yet worked out terribly. Still, the moves hardly came without flak; it signaled the end of Theo Epstein, who left town for the Cubs, and Terry Francona, who was essentially fired. Both will be in the Hall of Fame one day. Neither will forget about that season. Nor will the fans.
An eccentric move: hire Bobby Valentine as manager in 2012. That did not work out. Plenty of flak was received. Valentine lost his job and never worked in baseball again.
An obvious move: go all-in under Dave Dombrowski. The Red Sox signed David Price to the richest pitching deal in MLB history at the time, emptied the farm system for Craig Kimbrel and Chris Sale, and signed J.D. Martinez to fill the enormous shoes of David Ortiz. It worked, albeit with reasonable complaints over Price’s playoff performance at least until 2018, when hiring Alex Cora (another fairly obvious move; he was a highly coveted managerial candidate at the time) led to a franchise-record 108 regular-season wins and another championship.
Dombrowski received credit, but perhaps not as much as his predecessor, Ben Cherington, received in 2013, when a slew of more eccentric free-agent signings coalesced into the club’s third championship in a decade.
The truth is, Red Sox general managers receive just as much flak for screwing up the obvious moves as they do for whiffing on the eccentric ones, and arguably more credit for hitting it big with the eccentric approach.
Bloom is going with the eccentric.
“I think it’s important not to be afraid to do those things and not to be afraid of following your conviction when there’s something behind it,” he said. “Every time we’ve done that, it hasn’t always worked out. But I am proud we did that and I think I sleep better at night when I lead a decision-making process that results in us doing that. And it’s something we could stand to do even more, because ultimately, when you have a good process, even if it’s a process you’re always trying to improve, it’s going to work out more than not.”
One of the many oddities of the Red Sox front office turnover over the last 12 years is that all three general managers/presidents of baseball operations won at least one title before leaving town.
Epstein won two, then left for the Cubs and won another. Cherington won one, then left to teach college kids and is now back at the top of a front office in Pittsburgh. Dombrowski won one, was fired less than a year later and joined MLB expansion efforts in Nashville, only to later take over the Phillies and lead them to the World Series.
At one point or another during their tenures in Boston, all three of those men were hugely successful. But even the successful baseball executives have an expiration date.
The question is: how much success can you have before that date comes?
Since taking over for Dombrowski in 2019, Bloom has taken a long-term approach. Does it feel similar to what Cherington and Epstein were doing?
“In some ways,” said general manager Brian O’Halloran, a fixture in the front office through all four regimes. “And dating back to the beginning of this ownership group (in 2002), our goal from the very beginning was to build what Theo referred to as ‘The Scouting and Player Development Machine.’ We talk about it now, the pipeline of talent that comes through to form the core of your team. That’s the only way to sustain success in this game, no matter what your payroll is.”
From 1998 through 2011, the Red Sox never had a losing season. They won two titles and were still set up with a strong core as Epstein exited the organization.
Cherington, who came up through the player development side, had a similar long-term approach, but hit all his moves in free agency before the 2013 season, then never got to see his long-term investments pay off. He was stripped of his decision-making power in ‘15, when gigantic contracts to Rusney Castillo, Pablo Sandoval, and Hanley Ramirez severely backfired.
Still, when the Red Sox won it all under Dombrowski in ‘18, there was plenty of credit to be delivered to Epstein and Cherington, whose original signings and draft choices paid long-term dividends.
“That has been a goal from the very beginning,” O’Halloran said. “There have certainly been times where we have deviated off course. Usually, because we’re trying to accomplish something in the present. And some of those moves worked and some didn’t. But ultimately, where we are now, and how we’re operating now, is to try to eliminate that volatility and build that championship-caliber team every year. But the only way to do that is to have that talent coming through the pipeline.”
The difference these days is that the Red Sox are struggling to field a competitive roster at the big-league level and have as many questions about their talent in the minor leagues.
In a pair of rankings published in the last few weeks, ESPN ranked the Sox farm No. 14 while The Athletic ranked it No. 23, with evaluator Keith Law questioning whether they have a single arm in the system who can develop into a legitimate major league starting pitcher.
The perception now is that the Red Sox aren’t close to competing for a title anytime soon.
“We have to focus on what we think is best for the organization to achieve its goals,” O’Halloran said, “even if that isn’t what people are clamoring for because in the end, if we win, the fans will be happy. And our job is to win. That’s what we focus on.”
Winning fixes everything; it’s the golden rule in sports. Although in the case of the Red Sox, some might argue the opposite: winning ruins everything.
Had they never won that long-awaited World Series in ‘04 (and three more since then), but instead continued to fall just short again and again, would fans continue to flock in large numbers to see their fallible heroes try in vain to kick the football that Lucy (the Yankees) keeps pulling away?
One would have to believe they would, because they always did, even when seasons of perennial heartbreak stretched into decades. Even after fans grew accustomed to the most stunning, impossible defeats, they needed to see how it would play out, because maybe this time it would finally be different.
The attitudes today are much different.
That exercise has been replaced with the premature resignation that this season is over before it’s begun. Instead of hoping against hope now, as Red Sox fans did for 86 years, there seems to be, for at least the angriest fans, sadistic pessimism; it can feel satisfying to root against a team that surely won’t be good enough. It proves the fans right, and it sticks it to the stubborn front office that didn’t listen to them.
But for many fans, the demoralizing feeling of today is all too familiar: the idea that somehow, someway, the Red Sox will screw it up like they always do. They’ll fall further behind the Yankees, like they always have. And when October comes, fans will already be thinking of the following year’s roster, one that will have to be better than the one used this year, because there’s no way it could be any more disappointing.
The 2011 Red Sox were famously billed by this newspaper as “The Best Team Ever.”
Today, the Red Sox are facing the opposite problem.
The 2023 team might be “The Oldest Team Ever.”
And yet, it’s not terribly different from years before.
Some have compared it to the team in 2013, when Cherington signed a bunch of veterans on short-term deals. But that team was already loaded with superstar talent and cornerstone players at key positions; there was nothing random about the success of David Ortiz, Dustin Pedroia, Jacoby Ellsbury and Jon Lester
This year’s team has more of a 2015 feel. There’s no obvious Opening Day starter, which ought to prompt at least one good-humored clubhouse attendant to dust off the “He’s the Ace” T-shirts.
Everything is cyclical, especially in baseball, and while it might appear that the Red Sox are in the unpleasant part of the cycle, the last 20 years has taught us that it can turn at any moment.
“I’ll say I’m very optimistic about the future of the Red Sox,” O’Halloran said. “I think we’re trying to build something the right way. I think we have a good team for 2023, a team that should be able to compete in our division, to make it to the postseason, and hopefully play deep into October. I think we’re in the process of buildings towards something that can be sustained over time.”
Whether the fans like it or not.
“It doesn’t mean we’ll be right all the time,” Bloom said. “But if the only reason not to do it is because of what people say, that’s not a good reason.”
