Heyman: "The Yankees are again trying for (Justin Verlander). But I don't think they are confident"

Houston Astros pitcher Justin Verlander, coming off a Cy Young Award-winning season, is certain to be one of the most sought-after free agents on the market this winter.

The New York Yankees, often one of the biggest offseason spenders in the league, are looking to bolster their starting staff after being swept out of the 2022 ALCS by the eventual World Champion Astros.

It seems like a good match. However, MLB Insider Jon Heyman isn't so sure.

The Yankees are again trying for Verlander. But I don't think they are confident. - MLB Insider Jon Heyman, as quoted by @MichiganYankees

Justin Verlander, currently 39-years of age, was a unanimous choice for the 2022 American League Cy Young Award. He had an MLB-best 1.75 ERA and 0.83 WHIP while topping the AL with 18 wins to help the Astros to the World Series title.

After hoisting the championship trophy with his Houston teammates, Verlander opted out of the final season of his contract, making him a free agent. He was set to make $25 million with the Astros in 2023.

According to multiple reports, Justin Verlander is seeking a new contract on par with the three-year, $130 million contract that Max Scherzer signed with the New York Mets prior to the 2022 season.

Justin Verlander #35 of the Houston Astros participates in the World Series Parade

Yankees have courted Justin Verlander before

This isn't the first time that the Yankees have connected with Justin Verlander. After the 2017 season, New York courted Verlander. Instead, Verlander re-signed with the Astros, who had acquired him from the Detroit Tigers in a Deadline Day trade just a few months earlier.

Prior to this season, the Yankees again attempted to acquire Verlander's services, despite the hurler having thrown one game in 2020 and none in 2021. Verlander had undergone Tommy John Surgery to repair a torn ulnar collateral ligament in his right throwing arm.

Yet, Houston retained Verlander with a two-year, $50 million contract that allowed the star pitcher to opt-out after the 2022 season. Verlander opted out in hopes of securing his largest-ever deal in what will likely be his final contract.

Yankees have several free agent decisions to make

In addition to taking another look at Verlander, the Yankees have several free agent decisions to make. Topping the list: re-signing reigning American League MVP outfielder Aaron Judge. Judge, who broke the AL single-season home run record in 2022, is expected to sign a contract in the range of eight years, $332 million, according to projections.

If Verlander ends up jilting New York once again, the Yankees have other options for their starting staff. The list is highlighted by New York Mets starter Jacob deGrom and San Francisco Giants staff ace Carlos Rodon.