The MLB season is winding down, and the playoffs are right around the corner. The Boston Red Sox's chances of playing in October are quite high, as of September 5, FanGraphs lists them at 95.7%. That can make for a boring September.
While Garrett Crochet is still in the hunt for the AL Cy Young Award, though his start against the Guardians really hurt his chances, for the most part, no Red Sox are in the major award races. One thing fans should be watching for is individual milestones.
Three player milestones Red Sox fans should be on the lookout for in September
Trevor Story: First 30-30 Season
According to @Stathead, Trevor Story is the second player in MLB history (and the first in AL history) to have 25+ stolen bases without getting caught stealing.
— Gabrielle Starr (@gfstarr1) September 3, 2025
Trea Turner's 2023 season with the Phillies was the first. https://t.co/r7KE1RGc4G
Trevor Story's resurgence has been heavily documented (and a long time coming for Sox fans). He's most likely going to be the AL Comeback Player of the Year. He has been a perfect power speed combo in the middle of the Red Sox lineup.
Story has had two 30-home run seasons in his career, 2018-19, both in Colorado. He has never eclipsed 30 stolen bases; his career high was 27 in '18. Now, Boston's shortstop is just six homers and two stolen bases shy of the mark. The last Red Sox player to reach the milestone was Mookie Betts in 2018, and Story could join him by the end of the season.
Aroldis Chapman
The newly extended closer is having the best season of his career at age 37. Surprisingly, he isn't super close to having career-high marks in either of the major closer stats. He is nine saves shy of his career high (38) and over 40 strikeouts away (122). He already has his career low in ERA and WHIP; he'll just have to keep it.
The one thing to watch is walks. His improved command has been the talk of the season, and he currently has a career low in walks (14). He is only four away (18) from his career high, but has only allowed four walks in the last two months, and only one in August. While it might be more of a minor milestone, it is still extremely impressive in year 15 of his career.
Ceddanne Rafaela
Ceddanne Rafaela is having a true breakout season. Even through his streakiness, his numbers are extremely improved from last season, making his contract extension look like a brilliant move from Craig Breslow. He's already reached his career high in doubles, home runs, and tied his high in stolen bases.
What to watch with him now is hits and RBIs. It seems likely he'll reach his hits total; he needs another 15 to break that. RBI are going to be more of a struggle. His current high is 75 from 2024 he has 60 this year. He already has four RBI in September, but he only has two months this season with 15 or more. It'll take a big push from him down the home stretch, but hitting that career high would certainly be the stamp on a great season.