5 crucial decisions the New York Yankees have to make this offseason

After their season came crashing down in shocking fashion, the New York Yankees are now in offseason mode. The team will look to prepare for the 2023 season and there are plenty of issues that need to be addressed. Management are under heavy pressure after yet another disappointing finish.

The New York Yankees have not won a World Series since 2009. In fact, they have not even reached a World Series since 2009. This is the second-longest drought for a storied franchise that values success and championships over all else. The fact that the mighty Yankees have gone 13 years without a title is unacceptable to the fanbase.

Will the New York Yankees be able to hold on to Aaron Judge in the offseason?

Aaron Judge of the New York Yankees runs to the dugout at Yankee Stadium.

Brian Cashman and Hal Steinbrenner will be responsible for making the difficult decisions. After a 99-win season where the Yankees finished with one of the strongest offenses in the league, it's not all doom and gloom. The management will need to make adjustments and also address a list of pending contract issues in the offseason.

#5 Give youth a chance

The New York Yankees are famous for leaving young players in the minor leagues for too long. This year was another example of it. The Yankees only called up top prospects after a list of injuries depleted their lineup. Players like Oswaldo Cabrera and Oswald Peraza were presented with limited opportunities to prove themselves.

"Aaron Boone needed nearly two months to figure out that Oswaldo Cabrera is a better shortstop than Isiah Kiner-Falefa - something the entire Yankees fanbase could've told you at latest by mid-September." - Michael Bradburn

If the Yankees hope to have a team that can compete through 162 games and the postseason, they need depth in the lineup. An aging and injury-riddled lineup will only lead to another anti-climactic and heart-breaking finish.

#4 Address the shortstop position

An experienced and talented shortstop adds stability and confidence to the lineup. Unfortunately, the New York Yankees were all over the place with the position in 2022. Isiah Kiner-Falefa, Gleyber Torres, DJ LeMahieu, Oswaldo Cabrera, and Oswald Peraza all had stinks in the position.

There is top-tier shortstop talent available in the free agency market this offseason. Trea Turner, Carlos Correa, Dansby Swanson and Xander Bogaerts are all available if the Yankees choose to spend the cash.

The New York Yankees' top prospect, Anthony Volpe, is also regarded as one of the best minor league shortstops in the game. It is only a matter of time before he is given a chance in the big leagues.

#3 Target an elite MLB starting pitcher

The Yankees had two starting pitchers selected for the All-Star Game in 2022 in Gerrit Cole and Nestor Cortes Jr. Both those players are under contract.

The other three starting positions are up for grabs. Jameson Taillon will become a free agent at the end of the season.

Luis Severino will be 29-years-old before spring training and has not shown much improvement after seven seasons in the majors with the Yankees. The Yankees do have an option on his contract for $15 million next year.

Frankie Montas, who many at the organization rated highly, has been a flop since arriving in New York from the Oakland Athletics.

The decision to let go of Jordan Montgomery during the trade deadline looks like a massive misstep. The Yankees need to bring in established and experienced starting pitching if they hope to have any chance at a deep playoff run.

#2 Find a new manager

Aaron Boone has beared the brunt of the blame for the Yankees' woeful finish to 2022. The young manager has just completed his fifth season with the Yankees, but is yet to reach a World Series.

Boone has an above-average regular-season record with a .603 win percentage after 810 games. His postseason record, though, is far less impressive. After getting swept by the Astros this year, Boone has an abysmal 14-17 record in in the playoffs.

The Yankees consistently boast one of the highest payrolls in the majors. They have one of the most talented rosters on the field every year. The fanbase is loyal and committed. What more could Aaron Boone ask for?

#1 Finalize Aaron Judge's contract

If Aaron Judge does leave the New York Yankees this year, it will be a stain on Cashman and Steinbrenner's legacy. The continuous low-balls forced Judge to play out this season and enter free agency at the end of the season.

"HE DID IT! AARON JUDGE HITS NUMBER 62!" - Talkin' Yanks

After rejecting a seven-year, $213.5 million offer, Judge went on to have one of the greatest seasons ever witnessed by our generation. He led the MLB in home runs, RBIs, runs, OBP, slugging and OPS. He also broke a historic 61-year-old record when he hit 62 home runs to break the AL single-season record.

Judge is the favorite to win the 2022 American League MVP. The New York Yankees have only themselves to blame if they cannot close a deal for baseball's best player.