The New York Yankees have big decisions to make regarding two key players from their recent postseason runs. Aroldis Chapman and Didi Gregorius could both be headed for free agency, potentially ending their time in pinstripes.

Chapman is signed for the 2020 MLB season, but it’s unlikely that the two years and $30 million left on his contract will remain unchanged. The closer can opt-out of his deal this weekend, and he’s expected to do so if the Yankees don’t ink him to an extension.

Gregorius is no longer under contract. New York has until Monday night to extend a one-year, $17.8 million qualifying offer to their starting shortstop.

What will it take to keep both players in the Bronx?

Craig Kimbrel signed a three-year, $43 million contract with the Chicago Cubs in June. He’ll make $16 million in each of the next two seasons. An AL executive recently told’s Mark Feinsand that Chapman would get a higher yearly salary than Kimbrel this offseason, predicting that a four-year, $60 million contract could get the job done.

Chapman was named the 2019 American League Reliever of the Year, pitching to a 2.21 ERA and a 1.10 WHIP with 37 saves. The 31-year-old has made two straight All-Star appearances with 178 strikeouts in 108.1 innings pitched during that span.

The Houston Astros clinched a spot in the 2019 World Series when Chapman gave up a walk-off home run to Jose Altuve in Game 6 of the ALCS.

Gregorius got two hits in that Game 6, improving some poor playoff numbers. The shortstop hit .273/.314/.394 in 33 postseason at-bats, driving in no runs in the team’s last six games.

It was an overall disappointing 2019 campaign for Gregorius, who had seemed primed to sign a lengthy contract to start in the middle of the Yankees’ infield for the next several years. He underwent Tommy John Surgery in October 2018 and only hit .238/.276/.441 with 14 home runs in 82 regular-season games.

New York’s surplus of infielders might prevent the organization from offering Gregorious a big contract.

Starting second baseman Gleyber Torres is turning into a superstar and could shift to shortstop. DJ LeMahieu was the Yankees’ MVP and could play all around the diamond. Former AL Rookie of the Year runner-up Miguel Andujar is set to return from shoulder surgery. New York also has third baseman Gio Ursehela, who hit .314/.355/.534 in 132 regular-season games with brilliant defense.

Gregorius’ clubhouse presence can’t be overstated, and he seamlessly took over for Derek Jeter when the Yankee captain retired. A one-year deal could work for both sides as the 29-year-old looks to prove he’s worth a lucrative, multi-year contract.

Gregorius averaged 24 home runs and a .277 batting average from 2016-2018. He hit three homers and drove in 10 runs in 18 playoff games during that time.

Aroldis Chapman Yankees Cubs
New York Yankees relief pitcher Aroldis Chapman pitches against the Toronto Blue Jays during the ninth inning at Yankee Stadium in the Bronx of New York City on May 3, 2017. Reuters/Brad Penner-USA TODAY Sports