Biggest Questions Heading Into Each Wild Card Series of 2026 MLB Playoffs

Postseason baseball has arrived

Aug 30, 2026; Bronx, New York, USA; Boston Red Sox outfielder Roman Anthony (19) hits a single during the sixth inning against the New York Yankees at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | IMAGN IMAGES via Reuters Connect

It's finally time for the 2026 MLB playoffs.

With the regular season now in the rearview mirror, only 12 teams still have a chance to hoist the World Series trophy this fall. But first, four best-of-three series will determine who moves on from the Wild Card round. Here's one major question surrounding each Wild Card matchup.

Braves vs. Phillies: Which team actually has the favorable pitching matchups?

Sep 11, 2026; Atlanta, Georgia, USA; Atlanta Braves starting pitcher Chris Sale (51) throws against the Philadelphia Phillies in the first inning at Truist Park. Mandatory Credit: Brett Davis-Imagn Images | IMAGN IMAGES via Reuters Connect

It took the Philadelphia Phillies until the final day of the regular season to clinch the last Wild Card spot in the National League. After using veteran right-hander Zack Wheeler on Sunday, the Phillies are expected to start left-hander Jesus Luzardo for their first game against the Atlanta Braves on Tuesday. But Luzardo will most likely serve as more of an opener because he was just activated from the injured list.

The Braves, on the other hand, will probably give the ball to left-hander Chris Sale for the first game of this series. But after that, Philadelphia should have Cristopher Sanchez and Wheeler ready to start the last two potential games, while Atlanta would likely turn to Tyler Mahle and Grant Holmes. Although Mahle has pitched well since being traded to the Braves, late-series starting pitching could be one of Philadelphia's advantages in this Wild Card matchup.

Padres vs. Cubs: Will Pete Crow-Armstrong carry over his MVP numbers into the postseason?

Sep 19, 2026; Cincinnati, Ohio, USA; Chicago Cubs outfielder Pete Crow-Armstrong (4) bats against the Cincinnati Reds in the first inning at Great American Ball Park. Mandatory Credit: Katie Stratman-Imagn Images | IMAGN IMAGES via Reuters Connect

Chicago Cubs outfielder Pete Crow-Armstrong should be named the 2026 National League MVP. But now, the 24-year-old will look to replicate his regular-season success at the plate in the playoffs, starting with Chicago's Wild Card rematch against the San Diego Padres.

Although the Cubs eliminated the Padres from the postseason last year, Crow-Armstrong hit .185 (5-for-27) with no home runs in eight playoff games. If Chicago is going to go on a deep run in October, the presumptive NL MVP will most likely need to be a big part of that effort.

Astros vs. White Sox: How big of a factor will playoff experience be?

Sep 23, 2026; Seattle, Washington, USA; Houston Astros designated hitter Yordan Alvarez (44) steps out of the dugout to the on-deck circle before the first inning of a game against the Seattle Mariners at T-Mobile Park. Mandatory Credit: Joe Nicholson-Imagn Images | IMAGN IMAGES via Reuters Connect

The Houston Astros made history this year as the first MLB team to win a division with a .500 record. Winning the American League West at 81-81 also means Houston gets to host a playoff series against the Chicago White Sox. Chicago had its own historic regular season, going 84-78 and becoming the first team to earn a playoff berth after losing at least 100 games in the previous three seasons.

This is the first time the White Sox have reached the postseason since 2021. Meanwhile, the Astros have won two World Series titles in the past 10 seasons. While Chicago had a better record than Houston this season, it'll be interesting to see if the Astros' playoff experience gives them an edge in this first-round matchup.

Yankees vs. Red Sox: Is Aaron Judge going to play?

Sep 14, 2026; Minneapolis, Minnesota, USA; New York Yankees right fielder Aaron Judge (99) runs off the field after the first inning against the Minnesota Twins at Target Field. Mandatory Credit: Jesse Johnson-Imagn Images | IMAGN IMAGES via Reuters Connect

Arguably one of the biggest questions going into the postseason is whether three-time MVP Aaron Judge will be in the New York Yankees' lineup for their first game against the Boston Red Sox. Yankees manager Aaron Boone said last week the team wasn't planning to have the power-hitting outfielder on the Wild Card roster. But Judge provided his own status report one day later, saying that he was working toward being ready to play on Tuesday.

Judge participated in a live batting practice session at Yankee Stadium on Monday, but it's still unclear if he'll be in the lineup for New York's first playoff game against the Red Sox. While the Yankees won the second-most games in the American League with their captain sidelined for most of the season, how far they go in the postseason could depend on the 34-year-old's health.