Complacency is the estranged cousin of success.

One of the most dangerous things a team, player or fan base can be is satisfied with their accomplishments. It is the idea that resting on one’s laurels can lead to future prosperity. The reality is no two seasons are alike. The demands and requirements of every MLB team change year to year and the successful franchises set the pace. The worse thing an organization can do is actively work to maintain the status quo. The Yankees have to do everything they can to avoid the status quo this winter. All they need to do is look at their bitter rival.

The 2018 Boston Red Sox were a buzzsaw. Unfortunately, we are all way too familiar with that team. It felt like every player experienced a career year and every move the front office made was the right one. The end result was a World Series title. They entered the offseason in a prime position to maximize a run with their core players. Instead, they went to bed with complacency and woke up the next morning a jilted lover.

Citing payroll concerns, the Red Sox were content with bringing back the old gang. The team brought back Steve Pearce. They re-signed Nate Eovaldi. A damaged Chris Sale received a huge extension. The team didn’t bring in an outside free agent. In fact, more players left the organization than players who were brought in. Boston took a gamble on the past success of their core and believed that was enough to win again. That plan didn’t work.

The Yankees need to avoid the same trap. This is especially true because they don’t have a recent title to fall back on. At the end of the season presser, Brian Cashman repeatedly referred to his roster as a championship caliber one. The current version of the Yankees is extremely talented and despite season ending heartbreaks, has enjoyed an impressive run of success. With that said, there are critical questions facing the team this winter and they need to respond with the right answers.

Last week, I wrote about the Yankees needing to aggressively attack the free agent pitching market, but there are issues beyond the rotation. The roster has a clear need for a lefty bat. Despite the numbers showing the Yankees right-handed dominant lineup could handle righties, it was clear in the ALCS that lineup balance could’ve helped with their offensive woes. Is the team going to address this or will they be content with using the same lineup construction? Will they let Didi walk and attempt to fill his offensive production with the return of Miguel Andújar? Are they willing to look outside the organization and trade for a lefty bat? Is bringing back Brett Gardner and waiting for the return of Aaron Hicks all the Yankees need in Brian Cashman’s eyes? This winter presents an opportunity for the front office to fine tune a well oiled machine. They should take advantage of this chance.

Aroldis Chapman’s potential opt-out will be another test for the front office. If Chapman decides to opt out of his contract, the Yankees should seriously consider using that available money for a run at an elite starting pitcher. As Derek mentioned, it may be time to reconsider how the bullpen is framed in the overall picture of the roster. Looking beyond the game usage of the relievers, the strength of the team needs to shift to the starting rotation. The Washington Nationals are World Series champions today because of an organizational commitment to the rotation. Centering the bullpen as the main weapon of the team isn’t achieving the ultimate goal. It is time to reevaluate that approach and boldly institute a new one.

There are a lot of conversations about championship windows. These discussions largely focus on the amount of time talented players remain on a given team’s roster. The sustainability of these runs goes beyond how long good players remain together. Windows are reliant upon organizations refusing to be content with what they currently possess. Front offices continually need to be honest about how they can improve even if those improvements live in the details. This current group of Yankees are championship-caliber but are not champions yet. Cashman can’t just bring the old gang back for next year. Complacency can’t win out.