Red Sox point/counterpoint: Can Sox hang on to reach playoffs?

On Sunday, the Red Sox officially entered the final two weeks of the 2025 regular season. Maintaining their hold on one of the American League’s three Wild Cards will be an uphill battle. Boston’s remaining schedule – Athletics at Fenway Park, a road trip to Tampa and Toronto, and a closing trio at home with the Detroit Tigers – is among the most difficult in Major League Baseball. The Herald’s Red Sox reporters, Gabrielle Starr and Mac Cerullo, discuss the tightrope walk ahead. Gabrielle Starr: I know I’ve said this at least once in one of our previous iterations, but this season has absolutely flown by. I feel like the All-Star break was five minutes ago, but also the Rafael Devers trade feels like it was years ago somehow. The remaining 12 games will probably be over in the blink of an eye, too, but at this moment I can’t decide how I think they’re going to shake out. It’s been a difficult stretch for the lineup without Roman Anthony, and unlike the Yankees, whose remaining four series are against sub-.500 teams, the Red Sox have some extremely difficult opponents left. Do you think they can pull through and get to October? Mac Cerullo: October? Yes. I think they have enough of a lead over the Texas Rangers that they should be able to at least stay over the playoff cutline. But hosting a playoff series? That’s looking like a much tougher proposition. The Red Sox will need the Yankees to slip up, otherwise a three-game set at Yankee Stadium would become the club’s best case scenario. If the Red Sox stumble, they may be looking at a long flight to Seattle or Houston. Related Articles Red Sox score six in first inning, beat Yankees to avoid crushing sweep Talented young Red Sox pitchers settling in amid playoff push Red Sox lineups: Garrett Crochet looking to help avert sweep MLB notes: Breaking down the AL playoff race with two weeks remaining Red Sox place left-hander on injured list, recall Chris Murphy The road ahead GS: Well, let’s look at the remaining four opponents and how the Red Sox fared against them previously this year. They saw the A’s in Sacramento last week and went 2-1, with the loss being a winnable game (small consolation). The Sox are 8-2 against the Rays, but 3-7 against the Blue Jays; since they last met on June 29, Toronto is 42-24, Boston is 41-24. When the Sox went to Detroit in mid-May, they got swept in three games, including a blowout and back-to-back walkoffs. MC: The good thing about facing Detroit last is that by the time we get to the final weekend they might have already locked up the AL Central title and a bye to the division round. They’ll probably want to rest a lot of their starters, and at the very least it would make sense for them to either rest Tarik Skubal or limit his workload. As for the other series, the Red Sox have to beat the A’s at home. No doubt about that. And the Rays? They’ve had Tampa Bay’s number all season, so there’s no reason why the Red Sox shouldn’t go to Toronto in a solid position. The AL East is probably already out of reach, but who knows? If the Red Sox can sweep that series and get a little help, there is still a path. GS: The Red Sox may have had the Rays’ number all season, but that’s exactly the type of situation that worries me; they were 8-2 against the Yankees before this weekend, and the first two games were an unmitigated disaster. They’ve also struggled against more than a few bad teams and lost some very winnable games, so even though they should be able to beat the A’s, I’m not going to write this series off. The offense – or lack thereof – since Anthony’s injury is a big reason why. They entered Sunday hitting .232 with a .656 OPS in nine games since he went down, and though they staved off a Yankees sweep on Sunday night, they scored all six of their runs in the first inning and left six men on base in the remaining eight. MC: Anthony’s injury came at a horrible time, but the Red Sox should at least get Wilyer Abreu back later this week. That will help a lot. Pitching problem? MC: Obviously the Red Sox won’t get anywhere if they can’t hit, but their pitching situation will warrant close watching down the stretch. On Monday the club announced that Connelly Early will get the ball on Tuesday, Lucas Giolito on Wednesday and Brayan Bello on Thursday. One would imagine Garrett Crochet will pitch over the weekend in Tampa, but beyond that the club is going to have to piece things together for at least five of their last 12 games. Do you think Early, Payton Tolle and Kyle Harrison will be up to the task? GS: Early’s big-league debut against the A’s was historically spectacular, but I expect them to be significantly more prepared for him the second time around. Tolle’s debut was great as well, but he’s been hit hard and struck out only four batters over the two outings since, neither of which lasted longer than three innings. Of the three, Harrison has the most big-league experience by far. He may have made his Red Sox debut out of the bullpen, but I expect him to make at least one start, especially since Bello has struggled in his last three games; if the Sox can find a way to give him extra rest, they will. It’s clear the Red Sox pitching depth is much stronger than it was last year. The question is, do they have enough quality to get them where they want to go, or is it just quantity? MC: It’s honestly kind of amazing the Red Sox are even in the conversation considering how many injuries they’ve sustained on the pitching staff. Tanner Houck. Kutter Crawford. Richard Fitts. Hunter Dobbins. Cooper Criswell. If any of those guys were healthy and effective, imagine what a difference they could have made? And that isn’t even factoring in Patrick Sandoval, who won’t make it back in time from Tommy John surgery; Dustin May, who underperformed before getting hurt; or Walker Buehler, who flat out didn’t work out. That the club still has players of Early, Tolle and Harrison’s caliber available to help get them across the finish line is a luxury, but the Red Sox are asking a lot of them. GS: Hopefully they can meet the moment. Prediction time GS: Give me your prediction for these last two weeks? Will we have our first Red October since ‘21 or end up on the outside looking in again? MC: It may be stressful at times, but I think they’ll get it done. Put me down for the Red Sox finishing 89-73, good for the second Wild Card and a trip to Yankee Stadium on Sept. 30. GS: I’m a bit more cautious, so I’m guesstimating 88-74. Here’s hoping the best rivalry in baseball goes back to October.