The Boston Red Sox floundered against the Pittsburgh Pirates, dropping 2 of 3 over the weekend. With the Toronto Blue Jays simultaneously matching up against the league-leading Milwaukee Brewers, a series in which Toronto also dropped 2 of 3, the Sox missed a huge opportunity to close the gap in a tight AL East race.

September 1, 2025
Nick Zagzoug – Freelance Writer

Well, that was unfortunate. After sweeping the Orioles in Baltimore, the Red Sox had a golden opportunity to gain some ground on the AL East-leading Toronto Blue Jays and solidify their place atop the AL Wild Card standings. Instead, manager Alex Cora’s men lost the first two games of the series before salvaging a win against one of the worst teams in baseball. Boston now finds itself 3.0 games behind Toronto for the AL East and 2.5 games ahead of the Seattle Mariners in the Wild Card race. They have been leapfrogged by the New York Yankees in both sets of standings.

Fair play to the Pittsburgh Pirates. Though the team is careening toward yet another disappointing season finish, they have come a long way since the 12-26 start that saw Derek Shelton relieved of his managerial duties. Under new manager Don Kelly, the Pirates have played just below .500 baseball while being a thorn in the side of playoff-hopeful teams like the Blue Jays, Giants, Mets, Tigers, and Diamondbacks. They can now add the Red Sox to that list.

Payton Tolle Shines in Debut, Let Down by Dismal Bullpen

If you had Paul Skenes getting matched by a 22-year-old rookie debutante who was pitching for the High-A Greenville Drive to start the 2025 season on your bingo card, you may want to go buy a Powerball ticket ($1.1 billion jackpot on Labor Day). SP Payton Tolle sparkled in his major league debut, going 5.1 IP with 8(!) SOs while allowing 3 hits and 2 walks. The big lefty looked as composed as he did overpowering in his first start as a big-leaguer, registering 99 mph on his fastball and generating consistent whiffs on his secondary pitches. After Roman Anthony’s solo blast gave the Sox a 2-0 lead over the Pirates in the bottom half of the 5^th inning, Tolle vacated the mound, leaving 1 out and 2 men on base in the top half of the next frame. The Fenway Faithful erupted for the young hurler, recognizing that his job well done had put their team in a great position to win this game and set up a successful weekend against an inferior opponent.

Then RP Greg Weissert did his thing. 3 pitches later, the Sox’ 2-0 lead was erased. 1 pitch later, the Sox were down 3-2. RP Jordan Hicks could not stop the bleeding, giving up a run in what was another wild appearance (2 hits, 1 walk, 1 ER, 1 out registered). In total, Alex Cora used 5 relief pitchers to finish what was a promising start from Tolle in Friday’s contest.

Though this loss stings, the emergence of Payton Tolle as a potential mid/late-rotation arm could prove vital for a team searching for answers to its shallow starting pitching staff (see next segment). Walker Buehler who?

Dustin May, Brennan Bernardino Lay Eggs in Non-Competitive Blowout

Dustin May might just stink. After getting mashed by the Yankees in his last start (4.1 IP, 5 hits, 5 ERs, 3 BBs, 5 HRs), the righty trade deadline acquisition was hoping to get back on track against a struggling Pittsburgh offense on Saturday. Instead, May posted another atrocious stat line (5.1 IP, 8 hits, 6 ERs, 4 BBs, 1 HR). The Red Sox are 1-4 in May’s last 5 starts, with the pitcher earning the loss in each of the four defeats.

RP Brennan Bernardino did nothing to stop the game’s spiral, losing his command early in his appearance. Bernardino finished this outing with a similarly grotesques stat line (0.2 IP, 2 hits, 2 ERs, 2 BBs). By the time May and Bernardino had completed their handiwork, the Pirates led 9-2 in what finished as a 10-3 laugher. Boston’s defensive woes certainly did not help, as the team posted two more errors in the loss (CF Ceddanne Rafaela & 1B Romy Gonzalez).

Red Sox Salvage a Win on the Back of Gutsy Performances from Lucas Giolito and Jarren Duran

When was the last time the Red Sox had two inside-the-park home runs at Fenway in one season? After RF Wilyer Abreu hit an inside-the-parker at home against the Cincinnati Reds on June 30, LF Jarren Duran decided he would try one out for himself during Sunday’s game. Duran decided to one-up his teammate by scoring his standing up, though. It was the most exciting part of what was an all-around impressive offensive performance from the outfielder, who posted 2 hits, 2 walks, and 3 RBIs in the 5-2 victory.

SP Lucas Giolito continued his string of strong performances. The veteran right-hander was touched for just 3 hits and 1 ER in 6 IP. Giolito improved to 10-2 on the season, and the team improved to 4-1 in his last 5 starts. His start was held intact by RP Justin Slaten and RP Garrett Whitlock, who pitched one inning each, before Cora summoned recently-extended CP Aroldis Chapman to close the book on the Sox’ weekend series with the Pirates.

What’s next?

The 68-67 Cleveland Guardians are the next team passing through Fenway. Manager Stephen Vogt’s squad currently ranks third in the AL Central behind Detroit and Kansas City, and they sit 4.5 games out of a Wild Card spot. The Red Sox are expected to start SP Brayan Bello in the Labor Day matchup, then ace SP Garrett Crochet in Tuesday evening’s contest. After his strong debut, SP Payton Tolle may be given another opportunity in Wednesday’s series finale before the Red Sox travel to Arizona to face off against the Diamondbacks.