Why 2020 may be the Yankees’ best chance yet

The last decade has been filled with disappointment for the Yankees. They have not appeared in the World Series since their 2009 victory over the Philadelphia Phillies. Things could look different for the Bombers next season, though. Top contenders such as the Astros and Red Sox could be subject to losing a lot of talent to free agency and trades. This could open things up for New York to spend big and make it to the top of the mountain.

The Red Sox fired their President of Baseball Operations Dave Dombrowski, which gave the keys to Chaim Bloom to lead Boston in a new direction. There have been rumors of the Sox shopping the face of their franchise in Mookie Betts, and even though J.D. Martinez opted to return to the team in 2020, he could also be dealt.

Even with a roster that was set to compete last year, they won just 84 games and failed to reach the postseason. Now with their sights set on a semi-rebuilding year, they could be bumped way out of contention early next year. Plus, they will have some key players hitting the open market such as Rick Porcello, Mitch Moreland, and Brock Holt.

The Astros have had New York’s number in recent years. They eliminated the Yankees in 2015, 2017, and most recently, the heart breaker about a month ago. Houston’s roster will have a bit of a shakeup as well though. Cy Young runner-up Gerrit Cole is a free agent, along with both of their catchers, Robinson Chirinos and Martin Maldonado. They’ll also have some arms enter free agency like Collin McHugh, Wade Miley, Hector Rendon and Will Harris. The Astros’ roster could undergo major reconstruction in 2020. If they can’t retain Cole, that would be a huge blow to their rotation. I still expect them to be one of the best team in the American League, but the Yanks could have the better roster next year.

There are a few teams that will most likely remain in contention next year besides the ‘Stros. The Oakland Athletics, Minnesota Twins, Tampa Bay Rays. The Cleveland Indians are a borderline contender, but with rumors that they could trade Francisco Lindor and even Corey Kluber makes me think that they won’t be a force or don’t have the plans to compete in 2020 like they have in recent years.

So what does other teams’ free agents and possible trades have to do with the Yankees? Well for one, the Yanks won’t be losing a valuable free agent that can’t be replaced. They have already locked up Aroldis Chapman, and Brett Gardner will most likely re-sign as well. Didi Gregorius may not return, but Gleyber Torres can slide over to short and DJ LeMahieu could take everyday reps at second instead of rotating around.

Not only will the Bombers not have many important players walking, but they will also be looking to be buyers in free agency. Brian Cashman said he will do his due diligence on Cole and Stephen Strasburg in hopes to bolster the weakest link on the team. If New York lands one of those two, they could very well be World Series favorites.

The Yankees need to capitalize on this opportunity. Spending in free agency while other contenders may be moving backwards could be a direct path to the club’s 28th ring. There has been no better time in recent years than 2020 to hoist the Commissioner's Trophy.