The last-place Red Sox won’t be participating in this year’s postseason. But many former Red Sox players (and one former manager) have a chance to win this year’s World Series.
Here are the old friends to look out for this October:
WILD CARD ROUND
RAYS vs. GUARDIANS
The Rays-Guardians matchup that will open postseason play Friday includes a handful of former Red Sox.
On the Tampa Bay side, two lefties -- Jalen Beeks and Jeffrey Springs -- made cameos in Boston before joining the Rays. Beeks was one of the organization’s best pitching prospects before being traded for Nathan Eovaldi at the 2018 trade deadline; he has logged a 2.80 ERA in 61 relief innings this year. Springs struggled to a 7.08 ERA in Boston’s disastrous 2020 season but has reinvented himself with the Rays and tossed a 2.46 ERA and 3.04 WHIP in 33 appearances (25 starts) this season.
Two former Red Sox prospects are also part of Tampa Bay’s roster. Reliever Javy Guerra was a shortstop in Boston’s farm system who was included in the trade package that netted Craig Kimbrel from the Padres in Nov. 2015. Outfielder Manuel Margot, coincidentally, was also part of that package before ending up with the Rays.
Cleveland doesn’t have any former Red Sox on its roster but is managed by longtime Red Sox manager Terry Francona. Francona will manage against his good friend, Rays manager Kevin Cash, who spent two stints as a backup catcher in Boston during his playing career.
MARINERS vs. BLUE JAYS
The Mariners don’t feature any former Red Sox but a well-known old friend made Toronto’s wild card roster. Outfielder Jackie Bradley Jr. is back in the postseason for the second straight year after playing in last year’s NLDS with the Brewers. The 2018 ALCS MVP hit just .178 with one homer, nine RBIs and a .524 OPS in 40 games with the Jays down the stretch. He’s still a plus defender in the outfield.
Infielder Santiago Espinal is an ex-Red Sox prospect who was traded for World Series MVP Steve Pearce in June 2018. He has emerged a a consistent producer for the Jays this year and was even named an All-Star. Espinal hit .267 with a .692 OPS in 135 games this year.
PHILLIES vs. CARDINALS
The Phillies’ wild card roster includes Kyle Schwarber, who heads to the postseason with the third team in his career. The slugger was a major contributor down the stretch and into the postseason for the Red Sox last year as they reached Game 6 of the ALCS. Schwarber has mashed since signing a four-year deal with the Phillies in March; he led the National League with 46 homers in the regular season.
The Cardinals don’t have any former Red Sox.
PADRES vs. METS
The Padres don’t, either. But Mets reliever Adam Ottavino is back in the playoffs. Ottavino provided a stable force in the Red Sox bullpen last year and has been even better in New York this year, posting a 2.06 ERA in 65⅔ innings in front of All-Star closer Edwin Diaz. Ottavino will reach the postseason for the fifth straight year with a four different team. The Rockies made it in 2018, the Yankees in 2019 and 2020 and the Red Sox in 2021.
DIVISION SERIES (THESE TEAMS HAVE BYES)
ASTROS
When the ALDS gets underway next week, a couple of familiar faces will suit up in Astros uniforms. Catcher Christian Vázquez will play again in October after being traded to Houston at the trade deadline. He has taken a backup role to Martín Maldonado in Houston and has only hit .250 with a .585 OPS and three extra-base hits in 35 games.
A couple of former Sox prospects will suit up as well. Reliever Ryan Pressly, who has carved out a nice 10-year big league career, was taken out of Boston’s system as a Twins Rule 5 pick in 2013. Infielder/outfielder Mauricio Dubón has been on Houston’s bench this year; he was included in the Dec. 2016 trade that sent Tyler Thornburg to Boston and Travis Shaw to the Brewers.
YANKEES
Outfielder Andrew Benintendi, who joined the Yankees at the trade deadline, is out after having surgery to repair broken hook of the hamate bone in right hand. There’s a chance he’d be able to return if the Yankees make a deep run. Righty Frankie Montas, a former Red Sox farmhand traded for Jake Peavy in 2013, is also hurt and could be a bullpen or opener option if the Yankees reach the ALCS.
Marwin Gonzalez, who spent part of 2021 with the Red Sox before being cut, will likely make New York’s ALDS roster as a bench option. And long before he was a star for the Cubs and Yankees, first baseman Anthony Rizzo was a top Red Sox prospect who was traded to San Diego for Adrian Gonzalez in 2010.
DODGERS
For the third time in three years, Mookie Betts is in the postseason with the Dodgers. He had another excellent year, hitting .269 with 35 homers and an .873 OPS in 142 games. He’s not the only ex-Red Sox on the Dodgers roster, as veteran pitchers David Price and Craig Kimbrel are part of the bullpen. Price had a good year (2.45 ERA in 40⅓ innings) and is reportedly considering retirement after the postseason; Kimbrel has struggled down the stretch and is no longer the superstar he was. Reliever Chris Martin is a former Red Sox prospect who is on his seventh team.
The Dodgers are still managed by 2004 Red Sox hero Dave Roberts.
BRAVES
Atlanta’s bullpen includes Collin McHugh, who was with the Red Sox in 2020 but never pitched due to injury. Righty Silvino Bracho, who was briefly with Boston’s major league team this summer, also pitched for the Braves down the stretch. There aren’t many old friends on the defending World Series champions.
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