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But Can He Pitch?

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Payton Tolle, Connelly Early top prospect lists

Good morning! The Red Sox don’t have a third baseman, but they do have two of the best left-handed pitching prospects in baseball. MLB Pipeline put both Payteon Tolle and Connelly Early on their top-10 list: That’s Tolle in the number two slot, just behind Miami’s Thomas White, and Connelly Early landing at number eight. […]

Should the Red Sox sign free agent infielder Yoan Moncada?

Welcome back to the 2025-26 edition of Smash or Pass, in which we examine potential free agent and trade targets to determine whether the Red Sox should pursue them and what it would take to land them. Next up, a former top prospect. Who is he and where does he come from? He’s old friend Yoan Moncada, […]

Could the Red Sox finish in last place in 2026?

In the 19 years between 1993 and 2011, the Red Sox didn’t finish in last place in the division a single time. In the 14 years since 2011, they finished in last 6 times. The lean Chaim Bloom years were intended, according to Fenway Sports Group, to serve as something of a resent to avoid […]

As time runs out, what do the Red Sox do?

The Red Sox made it through Fenway Fest before the Alex Bregman news broke. After months of negotiations and all the work that went into acquiring him last year, the saga is over. Only a few people will ever know how whether the Red Sox were genuinely serious or if this was a pursuit designed […]

Where do the Red Sox go from here?

And how was your weekend? Yeesh. I’m still a bit shocked that Alex Bregman ain’t coming back to the Red Sox. I guess I just had too much confidence that something would’ve been figured out. Luckily, the gang here at OTM will be here to take you through the fallout of the third baseman signing […]

Alex Bregman signs free agent deal with Cubs; Red Sox left scrambling

The Chicago Cubs signed former Red Sox third baseman Alex Bregman to a bad contract tonight: five years, $175 million with no opt-outs. The Great Bregman Saga, which has consumed two consecutive offseasons for the Red Sox, is now over. The final line reads: 114 G, 18 HR, .273/.360./462, 3.5 bWAR, $40 million, 1 postseason […]

Reviewing David Ortiz’s groundbreaking performance on “The Masked Singer”

Perhaps the title of “Renaissance man” is thrown around too much. Sure, folks can be talented in multiple different disciplines of the arts. Culture is a broad spectrum that reaches billions, and the beauty of it is that its auteurs and practitioners can reach across any construct of division that might separate us: race, gender, creed, language […]

OTM Open Thread 1/10: Happy Fenway Fest!

Hello one and all, and happy Saturday. To those who will be in attendance: happy Fenway Fest to you and yours! I won’t be able to make it this year, sadly, as I missed the boat on ticket inventory. I gambled that the event wouldn’t sell out, and I lost. If it’s your first time, […]

The Red Sox can’t eat soup with forks. They need spoons

There’s a long history of people being associated with things they never *exactly* said. On July 15, 1979, exactly 18 months after I was born, Jimmy Carter gave a speech about a “crisis of confidence” in America that’s commonly referred to as the “malaise” speech, despite Carter never having used the word. But the brain […]

OTM Open Thread 1/8: Fenway Fest is Saturday

The Red Sox are set to host another edition of Fenway Fest this weekend, which looks to be heavily focused on players, autograph sessions, and stories of the 1986 team. It doesn’t appear there will be any sessions with ownership or the front office, which is unfortunate because those have provided some of the most […]

Red Sox News & Links: Sox reach arbitration agreement with Kutter Crawford

It’s the most exciting time of the offseason: free-agency arbitration agreement time! Tomorrow is the deadline for clubs and players eligible for arbitration to agree to new contract terms or duke it out in front of an arbitration panel. The Sox have five eligible players: Triston Casas, Kutter Crawford, Tanner Houck, Romy Gonzalez, and Johan […]

Red Sox sign minor league free agent Matt Fraizer

Who is he and where did he come from? He’s Matt Clyde Joe Teran Fraizer, and he comes to us from Clovis, California via the University of Arizona and the Pittsburgh Pirates minor league system. The Red Sox signed him as a minor league free agent last week after he was released by the Pirates. […]

Red Sox sign minor league free agent Matt Frazier

Who is he and where did he come from? He’s Matt Clyde Joe Teran Frazier, and he comes to us from Clovis, California via the University of Arizona and the Pittsburgh Pirates minor league system. The Red Sox signed him as a minor league free agent last week after he was released by the Pirates. […]

Red Sox truck day, spring training dates set

Good morning! Truck Day — as overexposed as it has become in the FSG era — is often likened to Groundhog Day as a harbinger of spring. So it’s kind of wonderful that, thanks to the World Baseball Classic, Truck Day is coming early this year and will land on actual Groundhog Day, February 2. […]

Phillies, Yankees enter the Bo Bichette market

Good morning! The holidays are over, it was 14 degrees in Boston this morning, and everyone is back to work. Thus begins the worst, most depressing stretch of the entire year. Can we at least get some interesting Red Sox news to hold us over? No, we can’t. But we can get unsourced rumors about […]