Xander Bogaerts, Chris Sale, Mookie Betts: a Boston Red Sox fan's guide to the Divisional Round.
The Boston Red Sox season is over after a Wild Card round sweep by the New York Yankees, but the Major League Baseball playoffs are just getting started as the Divisional Round begins on Saturday.
Are you a Red Sox fan looking for a team to root for? These former Red Sox players are still in action:
Chicago White Sox
The Chicago White Sox are littered with former Red Sox players and prospects after two trades over the last two seasons, including the blockbuster deal that sent Garrett Crochet to Boston. Making their first playoff appearance since 2021, the White Sox got their first series win since the 2005 World Series, sweeping the American League West champion Houston Astros in the Wild Card round.
Kyle Teel
Jul 21, 2023; Boston, Massachusetts, USA; Boston Red Sox draft pick Kyle Teel speaks to a media member prior to a game against the New York Mets at Fenway Park. Bob DeChiara-USA TODAY SportsOne of the centerpieces of the Crochet trade, the former 14th overall pick of the Red Sox, was an original member of the “Big 3” alongside Marcelo Mayer and Roman Anthony. After a productive first season in the big leagues in 2025, Teel played just 32 games in 2026 due to injuries, hitting .210/.336/.361/.697.
In Chicago’s Wild Card sweep of the Houston Astros, the 24-year-old went 3-for-10 with an RBI.
Chase Meidroth
A fringe top-10 organizational prospect during his time with the Red Sox, Meidroth has become a key piece of Chicago's infield in 2026. In 154 games, the former fourth-round pick hit .276/.350/.415/.765 with 16 home runs, while providing strong defense at second base.
Meidroth was a major contributor in the sweep of the Astros, going 4-for-7 with a home run and four RBI.
Braden Montgomery
Once the 12th overall pick in the 2024 MLB Draft by the Red Sox, the switch-hitting outfielder was the co-headliner alongside Teel in the Crochet trade. The 23-year-old outfielder made his big-league debut on June 9, hitting a walk-off home run. However, he struggled in his first taste of big-league action, hitting .226/.312/.350/.662 with six home runs in 93 games.
Jul 14, 2024; Ft. Worth, TX, USA; MLB Commissioner Rob Manfred takes a photo with Braden Montgomery after he was drafted by the Boston Red Sox with the twelfth pick during the first round of the MLB Draft at Cowtown Coliseum. Kevin Jairaj-USA TODAY SportsMontgomery went 2-for-8 in the White Sox' first playoff series victory since 2005.
David Sandlin
The 25-year-old right-hander was dealt to Chicago alongside Jordan Hicks ahead of the 2026 season in what was effectively a salary dump of Hicks' $25 million contract. Sandlin made his major league debut on May 27 and posted a 5.58 ERA in eight regular-season appearances. He tossed 1.1 scoreless innings in the Wild Card round.
Jordan Hicks
After being sent to Boston from the San Francisco Giants in the Rafael Devers trade, things never really clicked between the 30-year-old flamethrower and the Red Sox pitching brass. Hick posted an 8.20 ERA in 21 appearances for Boston in 2025. Boston sent him to Chicago alongside Sandlin in exchange for pitching prospect Gage Ziehl.
In 53 appearances for Chicago in 2026, Hicks posted a 3.94 ERA. He was excellent in the Wild Card round, striking out four over 3.1 scoreless innings of work en route to the sweep of the Astros.
Cleveland Guardians
For the second season in a row, a late-season surge propelled the Cleveland Guardians to an American League Central title. However, unlike in 2025, the Guardians got a first-round bye into the divisional round. They'll take on their divisional foe, Chicago, in a best-of-five series. They have no former Red Sox on their postseason roster.
New York Yankees
Sep 30, 2026; Bronx, New York, USA; New York Yankees players pose for a team photo after defeating the Boston Red Sox in game two of the Wildcard round of the 2026 MLB Playoffs at Yankee Stadium. Vincent Carchietta-Imagn ImagesIt would likely take an act of God to get any Red Sox fan to root for the Yankees to win their 28th World Series title. After a dominant sweep of Boston, New York will travel to Tampa to take on the top-seeded American League East Champion Tampa Bay Rays.
John Schreiber
Initially a 15th-round selection of the Detroit Tigers in the 2016 MLB Draft, the right-handed reliever was claimed off waivers by the Red Sox ahead of the 2021 season. The 32-year-old spent parts of three seasons with the Red Sox from 2021 to 2023, posting a 2.90 ERA in 111 appearances.
Schreiber was traded to the Kansas City Royals ahead of the 2024 season in exchange for Sandlin. After spending two and a half seasons, Schreiber was designated for assignment by Kansas City and claimed by New York on Aug. 31. The 32-year-old right-hander allowed only two earned runs in 11 regular-season appearances for New York. He tossed one shutout inning in the Yankees' sweep of the Red Sox.
Ali Sanchez
The 29-year-old catcher made four appearances for the Red Sox in 2025, going 0-for-2 in his only two plate appearances with the team. After becoming a minor league free agent at the end of the 2025 season, Sanchez signed a minor league deal with New York in December.
In 51 games for the Yankees in 2026, Sanchez hit .244/.275/.302/.577. He did not appear in the Yankees' Wild Card win over the Red Sox.
Tampa Bay Rays
Sep 22, 2026; Bronx, New York, USA; Tampa Bay Rays players celebrate after defeating the New York Yankees and clinching the American League East division title at Yankee Stadium. Brad Penner-Imagn ImagesOnce again, the Rays have found a way to be the best team in the American League, finishing the regular season 98-64, the third-best mark in baseball. Their prize for securing the AL East crown and a first-round bye? The Yankees, who finished the season with the second-best record in the American League, 93-68.
Steven Matz
The 35-year-old left-hander was traded to the Red Sox by the St. Louis Cardinals ahead of the 2025 trade deadline in exchange for corner infield prospect Blaze Jordan. Matz performed well in 21 relief appearances for the Red Sox, posting a 2.08 ERA.
He left for Tampa as a free agent, signing a two-year, $15-million contract with the Rays. After initially being used as a starter, Matz struggled to a 5.49 ERA in 36 appearances in 2026.
Cam Booser
After a series of tough luck injuries and a 50-game suspension due to a positive cannabis test, the left-hander retired from baseball in 2017. After rediscovering his fastball while hosting pitching lessons, Booser jumped between independent ball and minor league deals from 2021 to 2023, eventually landing a minor league deal with the Red Sox and making his major league debut in 2024.
After posting a 3.38 ERA in 43 appearances for the Red Sox, Booser was dealt to the White Sox in exchange for pitching prospect Yohiker Fajardo. After struggling in his lone season with Chicago, the 34-year-old signed with Tampa Bay in the offseason. In 42 appearances with the Rays in 2026, Booser put together a career year, posting a 1.98 ERA.
Los Angeles Dodgers
Baseball's modern-day evil empire, the Los Angeles Dodgers, enter their first postseason series of 2026 against the Atlanta Braves after a 100-62 regular season in pursuit of the third consecutive World Series title.
Mookie Betts
Oct 31, 2018; Boston, MA, USA; Boston Red Sox right fielder Mookie Betts (50) waves to the crowd during the victory parade to celebrate the Boston Red Sox World Series victory at Fenway Park. Paul Rutherford-USA TODAY SportsThe 2018 American League Most Valuable Player and World Series Champion, Betts, is the lone former Red Sox player on the Dodgers roster. After kicking off his Hall of Fame career with six seasons in Boston, Betts is now in his seventh season with Los Angeles. It was a down year for the now 33-year-old shortstop, as he hit just .257/.326/.454/.780 with 23 home runs and 69 RBI in 123 games.
Since joining Los Angeles, Betts has posted a .275/.358/.497/.855 slash line, adding three more World Series trophies to his collection.
Atlanta Braves
After claiming the National League East crown, Atlanta defeated their divisional foes, the Philadelphia Phillies, in a three-game Wild Card round at Truist Park. They'll now head to Los Angeles to kick off their toughest test yet against the back-to-back World Series champion Dodgers.
Chris Sale
Speaking of 2018 World Series champions, after a series of unfortunate injuries derailed the final two seasons of Sale's incredible run in Boston, the 37-year-old left-hander has experienced a career resurgence after being traded to Atlanta ahead of the 2024 season.
Oct 28, 2018; Los Angeles, CA, USA; Boston Red Sox pitcher Chris Sale celebrates after defeating the Los Angeles Dodgers in game five of the 2018 World Series at Dodger Stadium. Gary A. Vasquez-USA TODAY SportsAfter winning the 2024 National League Cy Young Award, Sale is expected to finish in the top three in voting again in 2026 after posting a 2.16 ERA in 27 starts. He got the start in Game 1 of the Wild Card round, allowing three earned runs on four hits over 6.1 innings and striking out nine. Much like the 2018 World Series, Sale came out of the bullpen in Thursday night's Game 3 win, recording the final four outs of the game, striking out three.
San Diego Padres
One of baseball's hottest teams in the second half, the San Diego Padres made light work of the Chicago Cubs in the Wild Card round, outscoring them 12-1 en route to a series sweep. They'll head to Milwaukee on Saturday to take on the National League Central Champion and top-seeded Milwaukee Brewers.
Nick Pivetta
After five seasons in Boston, where he posted a 4.29 ERA across 131 appearances, Pivetta signed a four-year, $55-million free-agent deal with San Diego ahead of the 2025 season. In two seasons with the Padres, the 33-year-old right-hander has reached a new level, posting a 2.87 ERA in 39 starts. He was limited to just eight starts in 2026 after missing an extended period of time with a right elbow injury.
Pivetta performed incredibly well in limited postseason action in Boston, allowing only four earned runs on nine hits, striking out 14 over 13.2 innings during the Red Sox's run to the 2021 American League Championship Series.
Pivetta got the start for San Diego in Wednesday's Game 2 win over Chicago, allowing one earned run on three hits, striking out four and walking two over 3.1 innings.
Xander Bogaerts
Oct 5, 2021; Boston, Massachusetts, USA; Boston Red Sox shortstop Xander Bogaerts (2) reacts after hitting a two run home run against the New York Yankees during the first inning of the American League Wildcard game at Fenway Park. Bob DeChiara-USA TODAY SportsA two-time World Series champion during his 10-year career in Boston, the 33-year-old shortstop is now in his fourth season with San Diego after signing a mammoth 11-year, $280-million free-agent deal ahead of the 2023 season.
Bogaerts has struggled as a Padre, hitting just .231/.332/.344/.676 in 153 games in 2026 and .261/.331/.391/.722 overall. The 33-year-old went 4-for-8 with a home run and two RBI in San Diego's sweep of Chicago.
Milwaukee Brewers
After a 103-win regular season, the reigning National League Central champions will look to change the narrative on their postseason failures and finally get over the hump, conquering the Dodgers. First, they'll have to get past the red-hot Padres.
David Hamilton
Initially an eighth-round selection of Milwaukee in the 2019 MLB Draft, the utility infielder was traded to Boston in December 2021 alongside prospect Alex Binelas and center fielder Jackie Bradley Jr. in exchange for outfielder Hunter Renfroe. After making his major league debut in June 2023, Hamilton appeared in 204 games for the Red Sox across three seasons, hitting .222/.283/.359/.642.
Hamilton was traded to Milwaukee alongside Shane Drohan and Kyle Harrison in the trade that sent Caleb Durbin, Andruw Monasterio, and Anthony Seigler to Boston. In 121 games for Milwaukee, the 29-year-old hit .245/.314/.336/.650.
Kyle Harrison
Sep 26, 2025; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Kyle Harrison (38) pitches against the Detroit Tigers during the first inning at Fenway Park. Eric Canha-Imagn ImagesThe centerpiece of the trade that sent Devers to San Francisco, Harrison allowed four earned runs on 14 hits in just 12 innings of work with the Red Sox in 2025. The emergence of Payton Tolle and Connelly Early, paired with the trade that acquired Sonny Gray and the free-agent signing of Ranger Suarez, caused the 25-year-old left-hander to fall out of favor in Boston, leading to the eventual trade that sent him to Milwaukee in exchange for Durbin.
Harrison looked like one of the best young starters in baseball at the start of the year, posting a 2.79 ERA in his first 21 starts. However, he limped to the finish line, posting a 16.05 ERA in his final seven appearances, and his struggles led Milwaukee manager Pat Murphy to move him into a bullpen role.
Shane Drohan
A fifth-round pick of the Red Sox in the 2020 MLB Draft, the left-handed pitcher spent the first four seasons of his professional career in the Red Sox organization before being selected by the White Sox in the 2023 Rule 5 Draft. After injuries prevented him from appearing in a game for Chicago, Drohan was returned to Boston.
After being acquired by Milwaukee, the 27-year-old left-hander started the 2026 season in Triple-A but was quickly promoted to make his major league debut on April 8. Drohan has been a valuable member of the Milwaukee pitching staff, posting a 4.19 ERA in 33 appearances.
Dustin May
After being acquired from the Dodgers ahead of the 2025 trade deadline, May struggled mightily during his brief stint in a Red Sox uniform. In six appearances with Boston, the then-27-year-old right-hander posted a 5.20 ERA before an elbow injury ended his season before the playoffs.
May signed a one-year, $12.5 million deal with St. Louis in free agency, where he posted a 4.38 ERA in 21 starts. He was dealt to Milwaukee ahead of the trade deadline in exchange for a pair of prospects. In his first 10 starts in a Brewers uniform, he struggled to a 5.65 ERA.


