At this point, what should worry you the most is more long term than short: the rebuild of the Red Sox is failing miserably.
And so, at the risk of sound hyperbolic and downright panic-stricken, you all need to stop referring to this as a bad start to the 2026 season. It is much more than that. Yes, the Red Sox won a game last night, but since the start of 2020 – the year they traded away Mookie Betts – the Red Sox are now 445-436, a winning percentage of .505 that ranks a perfectly mediocre 15th in baseball. During that span, the Red Sox have employed three chief baseball executives and turned the home clubhouse at Fenway Park into nothing more than a hostel, all in the name of rebuilding a baseball operation that has deteriorated into … what, exactly?
Now, for a moment, stop and ask your self this: among the Red Sox prospects who have been relentlessly promoted in recent years, which have lived up to the hype? Kristian Campbell might already be a lost cause. Roman Anthony now looks and sounds like he is being beaten down by the Boston experience, already asked to assume leadership that no 21-year-old should ever be asked to burden. Marcelo Mayer was all but beaten over the head this spring with questions about maturity, commitment and his desire to be great. Brayan Bello is every bit as inconsistent as he was three years ago. Ceddanne Rafaela still makes stupid mistakes.
CINCINNATI, OHIO – MARCH 29: Ceddanne Rafaela #3 of the Boston Red Sox reacts after lining out during the ninth inning of a baseball game against the Cincinnati Reds at Great American Ball Park on March 29, 2026 in Cincinnati, Ohio. (Photo by Jeff Dean/Getty Images)
The Red Sox haven’t put these young men into a position to succeed. In fact, they’ve done quite the opposite. Jarren Duran, for instance, was thrust into the big leagues when he shouldn’t have been, incapable of tracking fly balls until, say, 2023. (He debuted in 2021.) Even still, since the start of the 2024 season, Duran’s 13 errors in the outfield are the second-most in baseball. Just because he’s improved, that hardly means he qualifies as exceptional. Use your eyes. Just watch him.
And we haven’t even mentioned the trials of Tristan Casas, who is now injured yet again.
Ultimately, here’s the point: when the Red Sox were at their best in the early 2000s, their baseball operation whirred like a hummingbird. Prospects like Dustin Pedroia, Jacoby Ellsbury, Jon Lester and Jonathan Papelbon were not asked to burden major roles and become leaders from the moment they arrived. Pedroia and Ellsbury batted at the bottom of the order when they arrived, tucked under the sizable wingspan of people like Davis Ortiz, Manny Ramirez, Jason Varitek and others. Lester was sheltered by Pedro Martinez and Curt Schilling. Papelbon was a setup man late in 2005 and ascended rapidly, but he didn’t close until almost a year later. And he was an exception.
Those players were all allowed to focus on becoming major leaguers before they were asked to become centerpieces for production and accountability. What the Red Sox are doing now is akin to handing a 13-year-old and the family tax return and get to work. WHen that happens, you’re likely headed for an audit.
So what happens from here? Good question. But the current rebuilding of the Red Sox has already taken too long and, worse yet, might be failing. Chaim Bloom couldn’t keep the big league team competitive enough when he was here. Now the same is happening under Craig Breslow. The Red Sox haven’t had consecutive winning seasons since 2018-19, the second of which was an 84-win season that was an enormous drop from the 108-win, championship season of 2018. Dave Domborwski was fired as a result. Betts was traded shortly there after and the Red Sox adopted a new philosophy of treating star players with megacontracts as if they were radioactive.
Now here we are, several years later, and the Red Sox are still spinning their wheels. Maybe this approach can work in places like Tampa Bay, Minnesota or Cincinnati, where the pressure isn’t as great, the prices not as high, the noise not so loud. But it doesn’t seem to work here and it never has. Maybe the Red Sox will come out of this and maybe they won’t. In the meantime, we’re starting to wonder whether they will ever climb out of the cycle.
And we’re not just talking about the 2026 season anymore, either.
Tony Massarotti is the co-host of the number 1 afternoon-drive show, Felger & Mazz, on 98.5 The Sports Hub. He is a lifelong Bostonian who has been covering sports in Boston for the last 20 years. Tony worked for the Boston Herald from 1989-2008. He has been twice voted by his peers as the Massachusetts sportswriter of the year (2000, 2008) and has authored five books, including the New York times best-selling memoirs of David Ortiz, entitled “Big Papi.” A graduate of Waltham High School and Tufts University, he lives in the Boston area with his wife, Natalie, and their two sons. Tony is also the host of The Baseball Hour, which airs Monday to Friday 6pm-7pm right before most Red Sox games from April through October. The Baseball Hour offers a full inside look at the Boston Red Sox, the AL East, and all top stories from around the MLB (Major League Baseball).