The Yankees open a Wild Card series against the Boston Red Sox on Tuesday with a 93-win season already in the books and a second-base question waiting on the other side of October.

Jazz Chisholm Jr. is playing out a one-year, $10.2 million contract and is scheduled to reach unrestricted free agency after the postseason. New York once appeared likely to keep him long term. That path looks far less certain now.

Bleacher Report’s Zach Buckley projects the Yankees will instead turn to Pittsburgh Pirates second baseman Brandon Lowe this winter. Buckley has New York landing Lowe on a three-year deal worth about $25 million a season, or $75 million in total.

Lowe is expected to be among the strongest second basemen on the market and is not viewed as a lock to remain in Pittsburgh. Buckley has connected the two sides before, arguing general manager Brian Cashman could replace Chisholm with the Pirates infielder.

Cashman already has other roster work ahead. Third base, catcher and center field remain possible winter targets even if New York advances deep into October.

The immediate job is the Red Sox. New York will host the five-game series starting Tuesday night at Yankee Stadium. Cam Schlittler is lined up for Game 1, Max Fried for Game 2 and Gerrit Cole for a potential Game 3.

Lowe’s 2026 numbers are the reason clubs are expected to bid. He is hitting .260 with a .331 on-base percentage and a .493 slugging percentage. He led major league second basemen in home runs, slugging percentage and OPS.

His 5.4 wins above replacement ranked first among players at the position and tied for 15th in baseball. That figure sat just behind Junior Caminero, Randy Arozarena and Elly De La Cruz.

Chisholm still holds a clear edge in stolen bases. In most other offensive categories, Lowe has been the more productive hitter this season.

The Yankees would not be alone in the bidding. Buckley noted several teams are expected to chase Lowe, and the Toronto Blue Jays have already been mentioned as a possible landing spot.

Pittsburgh may try to keep him. Lowe said the Pirates have not opened extension talks during the season but left the door open.

“I think this team’s got a very bright future and a lot of good players, and there’s a lot of good baseball that’s going to be played in this park for a long time,” Lowe said. “[If] they want to talk, I’m all ears.”

If no multiyear deal is completed before free agency, Pittsburgh is expected to issue a qualifying offer in the $23.1 million range. Lowe is widely expected to decline it and test a market that has few middle infielders with his power.

MLB Trade Rumors ranked Lowe 10th among impending free agents entering the final stretch of the regular season. The site noted he had already reached 31 home runs for a second straight year and had flipped his defensive metrics after a poor 2025 with the glove.

That defensive jump is part of the case for a larger contract. Buckley wrote that second basemen often struggle to get paid, but Lowe’s power could make him an exception and push his average annual value to $25 million or higher.

For New York, the calculation is not only about replacing Chisholm’s production. It is about whether a 32-year-old power bat at second base fits a roster that still has holes at other positions and a luxury-tax payroll that rarely sits still.

The Yankees finished 93-68 and four and a half games behind the AL East champion Tampa Bay Rays. Boston came in at 87-75. Both clubs reached the wild-card round after uneven Septembers.

Schlittler gives New York a strong first-game option. He went 14-6 with a 1.95 ERA and 239 strikeouts this season and has dominated Boston in recent meetings, including a shutout-length start in last year’s wild-card series.

Once the season ends, Cashman’s winter will start in earnest. Chisholm’s next contract, Lowe’s market and the rest of the infield will be among the first items on the list.

A $75 million commitment would be a shorter, more targeted bet than the long extension once floated for Chisholm. Whether New York actually makes that bet will depend on October, competing offers and how much Cashman wants to change the look of the middle infield.