Toughest Free Agent Decision Each Wild Card Loser Will Have to Make

Following the last game of the Wild Card round in the 2026 MLB playoffs on Thursday, four more teams will begin to prepare for next season.

The Philadelphia Phillies, Chicago Cubs, Houston Astros, and Boston Red Sox were the first four franchises eliminated from the postseason. And now, these teams' front offices will have to start asking themselves some difficult questions about their 2027 rosters.

Here's one player that each team knocked out in the Wild Card round will have to decide whether to re-sign or let walk in free agency.

Phillies: Luis Arraez

Sep 24, 2026; Philadelphia, Pennsylvania, USA; Philadelphia Phillies second baseman Luis Arraez (4) prepares to bat during the third inning against the Milwaukee Brewers at Citizens Bank Park. Mandatory Credit: Bill Streicher-Imagn Images | IMAGN IMAGES via Reuters Connect

Luis Arraez and Alec Bohm are arguably the two biggest names on Philadelphia's 2026 roster who are set to become free agents this offseason. But Arraez's contact-first hitting style stands out as a unique skill set to pair with the Phillies' power bats like Kyle Schwarber and Bryce Harper.

Speaking of Harper, Philadelphia will likely want to decide whether the two-time MVP plays first base or in the outfield next season. That, in turn, could affect who the Phillies target in free agency. Either way, Philadelphia has some interesting choices to make about its 2027 roster, starting with whether to re-sign Arraez or Bohm.

Cubs: Ian Happ

Sep 4, 2026; Miami, Florida, USA; Chicago Cubs left fielder Ian Happ (8) runs toward third base against the Miami Marlins during the second inning at loanDepot Park. Mandatory Credit: Sam Navarro-Imagn Images | IMAGN IMAGES via Reuters Connect

Ian Happ has been with Chicago since the organization selected him with a first-round pick in the 2015 MLB Draft. The 32-year-old now enters free agency after hitting at least 21 home runs in four straight seasons. He's also a four-time Gold Glove Award winner in the outfield.

The Cubs had one of the most productive offenses in the majors this year. But that offense didn't show up in the playoffs, where Chicago was held to one run in two Wild Card games against the San Diego Padres. It's unclear whether that will force Chicago's front office to consider making massive roster changes.

The Cubs should be in the market for pitching this offseason. If that's the case, it remains to be seen whether they'll also pay to keep Happ on the only MLB team he's played for so far.

Astros: Daulton Varsho

Aug. 4, 2026; Houston, Texas, USA; Houston Astros center fielder Daulton Varsho (18) makes a catch on a fly ball during the third inning against the Toronto Blue Jays at Daikin Park. Mandatory Credit: Troy Taormina-Imagn Images | IMAGN IMAGES via Reuters Connect

Among the Astros hitting free agency this offseason, outfielder Daulton Varsho could be an intriguing name to monitor. The 30-year-old hit .172 in 41 games this year after being sent to Houston at the trade deadline, but he's considered an excellent defender in center field.

With the offensive firepower the Astros have elsewhere in their lineup, they could offer Varsho a short-term deal and hope for a bounce-back campaign at the plate in 2027. Either way, Houston might keep a close eye on the outfield market this winter.

Red Sox: Sonny Gray

Sep 23, 2026; Boston, Massachusetts, USA; Boston Red Sox pitcher Sonny Gray (54) delivers a pitch against the Cleveland Guardians during the first inning at Fenway Park. Mandatory Credit: Gregory Fisher-Imagn Images | IMAGN IMAGES via Reuters Connect

The Red Sox only have a few players who might become free agents this offseason. Among them, right-hander Sonny Gray has a $30 million mutual option with Boston that might not be exercised. If so, the 36-year-old could hit free agency after posting a 2.72 ERA and an 18-5 record in 29 starts for the Red Sox this season.

Heading into 2027, Boston's top of the rotation is expected to feature left-handers Garrett Crochet, Payton Tolle, and Ranger Suarez. So, Gray would be an important right-handed presence in that starting pitching staff. But after the Red Sox scored just two runs in their Wild Card matchup against the New York Yankees, it's unclear whether Boston will retain the veteran hurler or use that money to upgrade their offense.

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