Yankees once again learning the hard way with glaring past free agent miss

With each year that passes, it becomes more obvious that New York Yankees general manager Brian Cashman made a huge mistake (on multiple occasions) by not signing Kyle Schwarber. Now 32 years old, at the peak of his powers and coming off a 56-homer season as he enters free agency, Schwarber is looking at a payday in the realm of five years, $160 million, according to the latest prediction from The Athletic’s Jim Bowden.

That’s a lot of money, but Schwarber’s earned it with consistency and increasingly elite hitting over the past few seasons. This all makes the Yankees look sillier for not snagging Schwarber in 2020 or 2021 when they had the chance to, as they could have benefited from his bat over the last half-decade, at a far lower price.

In an alternate universe, Brian Cashman signed Kyle Schwarber to the Yankees years ago

As soon as Schwarber was released by the Chicago Cubs in December 2020, Yankees rumors started a-swirling.

Schwarber’s lefty power bat would fit perfectly at Yankee Stadium, pundits pointed out (duh). The Bronx would provide Schwarber with the opportunity to win another World Series. Michael Kay reminded us all that Cashman has always liked Schwarber’s game.

All the buzz led to nothing, however, as Cashman apparently didn’t pursue Schwarber with any zeal, and Schwarber ended up signing a one-year deal with the Washington Nationals.

Ironically, Schwarber was traded that season to the Boston Red Sox, whom Schwarber greatly aided in their run to the 2021 ALCS. Following the season, he declined his mutual option and became a free agent.

This was another opportunity for Cashman! But again, nothing doing. Schwarber ended up inking a four-year, $79 million contract with the Philadelphia Phillies, a figure that Cashman could have easily fit onto New York’s payroll by moving around a few pieces around.

Alas, now the days of Schwarber being underpaid have come and gone, and he’s just another free agent Cashman passed on when he shouldn’t have. The only remaining option is overpaying him and risking regression in the near future.

Schwarber is about to land a massive deal, and when you’re reminded of his winning qualities — as outlined by Bowden — you realize how overdue this contract truly is.

“In addition to being one of the premier power hitters in the game, Schwarber is highly valued around the league for his clubhouse presence,” Bowden wrote.

“Although he’s basically limited to the DH position, Schwarber offers consistency — he hit 56 home runs this year and has hit 40 homers or more in three of the last four years — and also durability, having played in 150 or more games each of the last four years, including 162 this year.”

“Every team except the Dodgers and Yankees should want him to be its DH,” Bowden continued. “Although the Phillies will make every effort to re-sign him, it will be fascinating to see what offers Schwarber gets on the open market for his special power bat and ability to mentor younger players.”

Indeed, the ship has sailed on Schwarber for the Yanks, and he remains Cashman’s white whale. Now, all New York can hope for is that Schwarber stays out of the American League by returning to Philly.