Yankees fans still don’t like the name Alex Bregman because it reminds them of the 2017 Astros sign-stealing scandal that ruined their chance to win the championship. Now that Bregman has chosen not to play for the Red Sox and is a free agent, can the Yankees accept a player who used to be their biggest playoff enemy?

Former Yankees outfielder Clint Frazier has made his position clear. “Alex Bregman is at the top of the Christmas list for the Yankees for me,” Frazier stated on his YouTube channel. “Yankees fans are still a little bit burned from that 2017 Astros team, so I don’t know if the majority of the Yankees fans would love this signing, but in my opinion, you’ve got to let bygones be bygones and just move on.” The scars run deep, though.

The loss to Houston in the 2017 American League Championship Series is still one of the franchise’s most painful defeats, and it hurt even more when the cheating scandal came to light years later.

And Frazier’s evaluation has significance beyond mere nostalgia.

He thinks Bregman will get five to six years and $150 to $180 million, which is a fair amount for a player who hit .273 with 18 home runs and 62 RBIs for Boston in 2025. “Hal Steinbrenner is going to have to open up that checkbook and give this guy what he wants,” Frazier argued. His argument is based on predictability.

Bregman was chosen for his first All-Star game since 2019 and brought veteran leadership to a young Red Sox clubhouse, which is exactly what the Yankees need at third base.

Craig Breslow, the Red Sox’s chief baseball officer, now has a big decision to make. Breslow has to choose between matching other teams’ offers or letting his All-Star go.

Bregman’s production stayed at an elite level even though he could only play 114 games because of a quad injury. He was a steady presence in the clubhouse for Boston’s youth movement, contributing offensively and playing great defense at third base.

However, the Yankees acquired Ryan McMahon at the trade deadline, so it’s unclear how interested New York is. However, Bregman’s consistent playoff performances and proven ability to deliver in high-pressure situations make him an interesting option for any contender willing to overlook past problems.

Trent Grisham gives Yankees unexpected offseason decision

The New York Yankees are dealing with their own surprising success story while the Bregman situation plays out. Trent Grisham, who was just a throwaway piece in the Juan Soto trade, turned into something no one expected.

The 28-year-old center fielder had a career-defining season with 34 home runs, a .811 OPS, and 3.5 WAR. This made him the team’s best leadoff hitter against right-handed pitching.

Brian Cashman has five days after the World Series ends to decide if he wants to give Grisham the $22.05 million qualifying offer. The stakes are important because this breakout season changed Grisham from an afterthought to a real trade asset.

New York Post’s Joel Sherman proposed an inventive workaround on Tuesday. “If Grisham accepts the qualifying offer and the Yankees ultimately sign Bellinger, I do not think it is impossible for the Yanks to trade Grisham.”

Sherman added, “They would have to take a salary back or eat some money, but center field and offense are in short supply, so as long as it is not the full $22.05 million, then I could see the Yanks being able to move Grisham.”

Sherman came up with a tremendous idea.

Sending Grisham across town to the Mets for reliever Clay Holmes. Holmes costs less, but he can leave the deal after 2026.

Ideally speaking, teams can be creative when balancing the need to build a roster and allocate funds in today’s market.