CLEVELAND -- Ben Cherington followed Theo Epstein as general manager of the Boston Red Sox after the 2011 season, and over the next three years, the team fostered what might have been the best farm system in baseball. Matt Barnes, Jackie Bradley Jr. and Mookie Betts, all developed effectively, with infielder Xander Bogaerts just ahead of them.
Meanwhile, at the big league level, a series of short-term free-agent signings paid off, and the Red Sox won the 2013 World Series. For all of that success, Cherington was demoted in the summer of 2015 -- effectively fired as the head of baseball operations.
His replacement was Dave Dombrowski, who did the bidding of ownership and worked aggressively to augment the team, using assets from Cherington's fertile farm system and the team's substantial financial resources and adding Chris Sale, Craig Kimbrel, David Price and others. The Red Sox won the World Series in 2018, after 119 wins and arguably the greatest performance in franchise history. And less than a year later, Dombrowski was fired.
Two World Series titles in six years, and two executives -- with two very different personalities, operating very differently -- both dismissed. These decisions loosely frame the industry perception of the Red Sox as a chaotic company, a miserable place to work. Boston owner John Henry needs to understand this, because it is why some of the people he'd probably love to consider as possible replacements for Dombrowski privately dismiss the idea out of hand.
They saw what happened to Cherington. They saw what happened to Dombrowski.
In fact, a wide-held view in other front offices is that the highly respected and well-liked Red Sox president Sam Kennedy stands as a thin buffer between the team devolving to the level of the Mets, the team generally regarded by rival executives as baseball's model for dysfunction. "If Sam ever walked away," said one official, "the whole thing would be a complete mess."
The Red Sox will eventually hire somebody good for the job, and in theory, it's a great job -- running baseball operations for a wealthy team steeped in history and legacy, in an iconic market packed with passionate fans. When Henry's time as owner is completed, his tenure will be viewed as an extraordinary success -- the 2004 comeback and breakthrough championship, and the three titles that followed.
But in this time and place, highly qualified evaluators wave off the idea of working for Henry because they doubt that he'd have the patience to back his next general manager through the difficult crossroads ahead.
The Red Sox must make a hard and perhaps unpopular choice with Betts, their best player, who is eligible for free agency in the fall of 2020. They have to ride out the contracts of three veteran pitchers with daunting injury concerns -- David Price, Chris Sale and Nathan Eovaldi, who are owed about $80 million combined for the next three seasons, obligations that will greatly restrict the team's other work.
Meanwhile, the Red Sox are surrounded by functionality in the AL East. The rival New York Yankees -- a team once renowned as the most chaotic, under George Steinbrenner's stewardship -- are run with almost complete symbiosis, from owner Hal Steinbrenner through GM Brian Cashman to Aaron Boone and his staff. The Blue Jays are poised for progress, around a strong core of young position players. Even the Orioles have the ground floor of a long-term plan.
Henry needs to recognize that his franchise is extremely vulnerable in this moment, and if he yanks the steering wheel in different directions in the critical years ahead, impatiently ejecting chosen executives and plans along the way, he could spin the Red Sox right into the sort of hole that Steinbrenner drove the Yankees into in the mid-'80s. (It was only when Steinbrenner got out of the way and entrusted Gene Michael and Bill Livesey and others that the Yankees rebounded in the mid-'90s.)
Henry must somehow get his shop back to a place of equilibrium. Deferring to Kennedy through this process would be a good start, because it will be Kennedy who will have to convince leery candidates that it's possible that the Red Sox can be operated with confident circumspection. Right now, there is a mountain of doubt about that.
News from around the major leagues
The Yankees have been a model of resiliency this year, winning over 100 games in spite of a ridiculous, nonstop series of injuries. But the Cleveland Indians, who will face the Phillies on Sunday Night Baseball (6:30 p.m. Eastern start time) while in the midst of the American League's wild-card race, have contended under similar circumstances.
Cleveland (91-64) lost star shortstop Francisco Lindor for the first month. Only two starting pitchers have had more than 20 outings for them -- the emerging Shane Bieber, who is likely to finish third in the AL Cy Young Award voting, and Trevor Bauer, who was dealt away before the trade deadline. Corey Kluber, greatly limited by various injuries, has made just seven appearances this year and didn't fare well, with a 5.80 ERA. Mike Clevinger missed more than two months with an upper back strain. Danny Salazar's return lasted one outing.
Third baseman Jose Ramirez suffered a broken hamate bone and hasn't played since Aug. 24 -- although Ramirez took batting practice here Saturday afternoon and could be back in action as soon as Sunday night. Second baseman Jason Kipnis is out for the rest of the year, after he, too, broke a hamate bone. Bradley Zimmer, long viewed as the center fielder of the future, has two plate appearances this year. The Indians have fielded 11 different outfielders in 2019. All-Star closer Brad Hand has dealt with arm trouble lately, although he looked very good in relief Saturday, throwing his fastball as high as 94 mph, and spinning sharp sliders.
In spite of all that, the Indians could finish this season in the range of 95 wins, and perhaps make the playoffs. After Sunday night's game, they'll start a stretch on the road that could take them through as many as five cities -- Chicago and Washington, to face the White Sox and Nationals in the last games of the regular season; perhaps a play-in game against the Rays in St. Petersburg, possibly followed by a wild-card game in Oakland; and the first two games of the division series.
• Once the Indians complete their season, they will have a difficult decision with Kluber: They hold a $17.5 million option on the two-time Cy Young Award winner, who turns 34 next April. Just last year, Kluber threw a league-high 215 innings with a 2.89 ERA, and he has reached the age when concerns grow about mileage and injuries.
The Indians will presumably decline their 2020 option on Kipnis, and choose instead to give him a $2.5 million buyout. Lindor made $10.85 million this year and will get a healthy raise through arbitration for 2020.
• John Middleton, the principal owner of the Phillies, has remained mostly silent as his team drifted late in this season, so it's unclear how feels about its 2019 performance, and whether he attributes some of the inconsistency to injuries (Andrew McCutchen, Jake Arrieta, David Robertson, etc.), or if he has larger concerns. He has demonstrated a willingness to step in when he feels it's necessary -- he was the driving force behind the pursuit of Bryce Harper in free agency, and the firing of hitting coach John Mallee and the temporary shift of Charlie Manuel into Mallee's former role.
While there has been a lot of speculation about the status of manager Gabe Kapler, but the relationship between Kapler and the front office is perceived to be rock-solid. The larger and more pertinent question that hangs over the team is how Middleton feels.
• If the late-season slide of the Chicago Cubs concludes with the team out of the playoffs for the first time since 2014, this will likely serve as the end of Joe Maddon's time with the team. But there may be other significant changes as well, with the front office pursuing ways to adjust the makeup of the roster.
Last winter, the Cubs made it clear to other teams for the first time that they were open to offers for third baseman Kris Bryant, but didn't get any traction toward a deal. They could push harder for a Bryant trade this winter, now that he's one year closer to free agency. Bryant is represented by agent Scott Boras, who almost always takes his clients into free agency, and Bryant could be eligible to hit the open market after the 2021 season.
Bryant is liked by teammates, but his trade value will never be higher than it is this winter, off a good season, and the simple matter is that the Cubs are looking for a different mix of players. Theo Epstein, the team's head of baseball ops, has been outspoken about what he considers to be a lack of urgency and attention to detail in the team's play. For example: The Cubs have lost more runners making outs on the bases than any team in baseball this year.
Among the Cubs with expiring contracts: left-hander Cole Hamels, relievers Brandon Morrow, Pedro Strop, Derek Holland and Steve Cishek and super-utilityman Ben Zobrist. The Cubs also hold a team-friendly option on left-hander Jose Quintana.
• Some agents who don't represent right-hander Zack Wheeler believe that the Mets will tender him a qualifying offer of $18 million. If that happens, then Wheeler will have two choices -- accept the one-year deal before hitting the market again next fall, or reject it and be tied to draft-pick compensation as he goes into free agency.
If the Mets attempt to keep their current rotation into the start of the 2020 season -- Jacob deGrom, Marcus Stroman, Noah Syndergaard, Steven Matz and Wheeler (perhaps on that qualifying offer) -- it would cost them about $75 million in salary.
• After a long summer of rehabilitation, Dellin Betances's big league season lasted all of two batters, before he partially tore an Achilles tendon. The timing could not be worse for him, within the context of the business side of baseball: Betances, 31, is a free agent this fall for the first time.
There are evaluators and agents who believe that Betances' best play at this point is to work out a one-year deal with some team, betting on himself to rebound in 2020, and then hit the market again next fall. Betances could seek opportunities to close with teams other than the Yankees, but considering how teams evaluate relievers these days -- let's face it, front offices just don't care about saves -- it will be more important for him to just get back to being a dominant late-inning force, regardless of whether it's in New York or some other club. Given his mileage, his 2019 injuries and the general volatility in reliever performances, evaluators will want to see a larger sample size of success from Betances.
During his career, Betances has averaged 14.6 strikeouts per nine innings, with a 2.36 ERA in 358 games. It will be interesting to see if the Mets, with a bullpen makeover to look forward to this winter, get involved in the bidding for Betances, who was born and raised in New York.
Baseball Tonight Podcast
Friday: Karl Ravech on the future of Joe Maddon, and the excellence of Jack Flaherty; Jessica Mendoza discusses the Indians' resiliency; and Rena Banena's Friend Zone advice and Bleacher Tweets.
Thursday: Barry Zito discusses his career and life with incredible honesty -- the insecurity, and how stardom and money affected his personality; Tyler Kepner of The New York Times digs into Bruce Bochy's milestone, and some emotional moments for the Yastrzemski family at Fenway; Sarah Langs and The Numbers Game.
Wednesday: Keith Law on the explosion of relief pitchers, and Felipe Vazquez 's legal trouble; Tom Haudricourt of the Milwaukee Journal Sentinel on the Brewers' surge; and this week's Power 10.
Tuesday: David Schoenfield digs into the changing MVP races in both leagues; the question marks for the Dodgers; Langs and The Numbers Game.
Monday: A fun conversation with the Dodgers' Walker Buehler; Tim Kurkjian on the season-ending injury to Mike Trout, a frightening injury to Charlie Culberson, and the Cubs' chances; and Todd Radom's weekly quiz and cap talk.