Jeremiah Jackson takes seat after rough game

On a conference call, Cashman told reporters that he and the Yankees had agreed on a new deal, but they are “just hammering out the final details.” Despite the Yankees being a perennial contender and advancing to the AL Divisional Series again this season, the fanbase has grown a little frustrated by the lack of World Series titles this century. Cashman has held the job since 1998 and has led the Yankees to 29 consecutive winning seasons, six pennants, and four World Series, but the Yankees have not won a title in 17 years and have only one championship in the last 26 seasons. For a franchise that is used to being at the top of the sport, the recent performance allowed some fans to believe the Yankees wouldn’t simply run it back again in 2027. That appears to be exactly what they’re doing.

Woodruff is hoping to be included on the Brewers’ World Series roster after missing the last 4 1/2 months with a shoulder injury. His velocity apparently is back close to the 91.8 mph he averaged with his fastball in nine starts before going down this season. Still, it seems like something of a long shot that he’ll be activated.

Sandridge, a 27-year-old reliever, opened the season on the Orioles’ 40-man, but he gave up six runs in 5 1/3 innings in six appearances for Triple-A Norfolk and then missed the rest of the year, The left-hander has made one career major league appearance, giving up two runs in two-thirds of an inning for the Yankees in 2025.

Medick, 35, spent the last four years in the Yankees’ system, serving as a Triple-A pitching coach this year. He had a very brief career in the minors in the Diamondbacks’ system, posting a 1.17 ERA in 30 2/3 innings as a Rookie-ball reliever in 2014. That wasn’t enough to keep him around, though, and he finished his pitching career in indy ball in 2018.

Chandler Rome says it’s unclear if the team is still considering any of its current assistant GMs — Charles Cook, Gavin Dickey and Connor Huff — for the head job replacing Dana Brown, who was let go in August. Kleine, Barfield and Flores are all assistant GMs for their teams. Kleine previously interned for the Astros in 2007 before being hired by the Brewers and working his way up.

The rule for replacing injured players in the postseason is that it has to be a new injury, so the Brewers might be stuck with Woodruff on the roster and unable to pitch if something goes wrong. Woodruff hasn’t pitched since June because of a shoulder injury that was originally thought would require season-ending surgery. If he’s added to the World Series roster, it could be at the expense of Kyle Harrison, who has yet to pitch in the postseason.

The 19-year-old had an inconsistent first full professional season, hitting .242/.427/.403 in 36 games with four home runs and 12 steals. However, he also had a 35/40 K/BB ratio and showed elite plate discipline. Kilby is hitting .290 with a .964 OPS in Arizona Fall League action and now has four steals. He should begin next season in Single-A, and it remains to be seen what his long-term positional fit is with George Lombard Jr. now up with the Yankees at shortstop.

Rodríguez allowed one hit but struck out two in his inning of work. Perhaps more importantly, he sat 96.5 mph, which was up from 95 mph in his first outing, and he touched 98 mph on the radar gun. The 27-year-old has yet to allow a run in his AFL action and could be the favorite for saves in San Francisco heading into the 2027 season.

Peete was everywhere in this one. The 21-year-old now has six steals, three doubles, and two triples in AFL action, while hitting .361 with a 1.091 OPS. Peete, who came over in an offseason trade for Brendan Donovan, missed over two months this season with an illness, but finished the year strong at Double-A. He figures to start there again in 2027, but a hot start, paired with his strong AFL results, could lead to a Triple-A promotion in short order.

Murray reported that many teams expressed interest in acquiring Kwan at this year’s trade deadline, but the Guardians saw a chance to make a playoff run and opted to hold onto their outfielder. Now, with Kwan entering the final year of his deal and the Guardians unlikely to sign him to an extension, the market for him is likely to heat up again. Kwan had a down year in 2026, hitting .282/.382/.349 with three home runs and 32 RBI; however, he was sixth in baseball in WAR from June 30 to the end of the regular season, and some teams may see that as a sign that he is due for a bounce-back in 2027.