The Yankees have made the postseason in each of the past three seasons and so far have lost twice to the eventual World Series Champions. That tells us two things: the American League has some power house clubs, and the Yankees have been able to put themselves right up there with them. Even though the Bombers have come up short, one thing that can’t be denied is that the Yankees have continued to look better each season.
Since 2016 when the Yankees traded Aroldis Chapman, Andrew Miller, and Carlos Beltran, they’ve formed a core of players with the likes of Aaron Judge, Gary Sanchez, Gleyber Torres, and more. It’s no secret this core has shown an incredible amount of talent that could eventually lead them to a fall classic. The recent addition of DJ LeMahieu atop of the order highlights the fact that the Yankees organization must take advantage of each free agency pool.
Building from within has allowed the Bombers to field young talented players who are currently under contractual control and will be for the foreseeable future. Aaron Judge and Gary Sanchez won’t be free agents until the end of the 2022 season. They might be the first wave of core players testing the market if the Yankees don’t extend their contracts. In other words, they have an opportunity to keep this same offense together until then with a contract extension or resigning of DJ LeMahieu. This offense was one of the best in the major leagues, and even though the Yankees can tinker around at the shortstop position this offseason, what could make their numbers even more impressive next season is health.
As they have improved over the last three years, one constant has been an elite bullpen featuring Aroldis Chapman, Dellin Betances, and Chad Green. This offseason not only will Dellin Betances possibly be a free agent, but Aroldis Chapman has the opportunity to opt out as well. This shouldn’t be a cause for panic because the Yankees have shown that maintaining a strong bullpen is part of their blueprint. Even though most fans are hoping for the return of Betances and Chapman, if only one is able to return, another option could be southpaw Will Smith. Arguably the Yankees added the two best relievers last offseason in Zack Britton and Adam Ottavino and could look into doing so again.
With an offense pretty much set until 2022 and a clear desire to keep a productive bullpen in the Bronx, the only thing missing the past few years has been starting pitching depth. That’s why this particular free agency pool couldn't be better suited for the Yankees’ front office. The one area they haven’t been able to cover since turning around the direction of the team in 2016 is now the area where free agency will be strong. Names like Gerrit Cole and Stephen Strasburg lead the headlines, while Madison Bumgarner, Hyun-Jin Ryu, Dallas Keuchel, Jake Odorizzi, and Zack Wheeler are candidates as well.
The Bombers did miss the World Series this decade, but the they spent the second half of the decade assembling a team that could dominate the next one to come. Missing out on starting pitching—whether it was through trade or free agency—has been thrown around as the reason for their early postseason exits, and it would be difficult to argue against that. Fortunately for the Yankees, there are so many starting pitching options in this free agency pool, and that makes this offseason different from previous trade periods and free agencies where only one or two big names were available. So much work has been put into making a talented team with depth in just about every position, it’s time for the Yankees to acquire the last piece of the puzzle and there couldn’t be a better time.