For the winningest franchise in MLB History, this stretch has been a disappointing one for the New York Yankees as they have failed to win a World Series crown since 2009. The organization has arguably been giving the utmost financial resources to add MLB superstars like Gerrit Cole, DJ LeMahieu, and Joey Gallo. However, talent and big names are not the sole reason for any squad to win the World Series.

With the players association and the league finally wrapping up the disputes on their agreements, the regular season will finally begin on April 7. New York has a plethora of free agents to sign to fill in their weaknesses in their rotation, bullpen, and shortstop positions, respectively,  but there are some individuals that must avoid in this current free agency. Front offices will be heavily challenged to act quickly because Spring Training is already beginning on the weekend. The Yankees have the edge because of their track record and money they could offer, but this will be one of the most exciting days for any baseball fan.

Yankees Free Agency Breakdown

Clayton Kershaw

There is no doubt that the pitching rotation of the Yankees has been questionable for several seasons already. Manager Aaron Boone has been having trouble finding reliable arms after Cole, especially with the departure of Masahiro Tanaka and issues revolving around Luis Severino and Domingo German. However, Clayton Kershaw would not be the answer because of his unfortunate to fold on the high pressure situations.

The Los Angeles Dodgers have been one of the tremendous teams in the league as well as their pitching rotation last season of Max Scherzer, Walker Buehler, Trevor Bauer, and Julio Urias was impeccable. Kershaw sustained a forearm injury right before the playoffs, which forced Manager Dave Roberts to not utilize him at the brightest lights. This could have been a blessing in disguise as he was not in a position wherein he could have possibly failed to reach the tremendous expectations. With the Yankees already relinquishing leads because of their pitching, adding Kershaw will not be the answer to their successive exits.

Zack Greinke

Another veteran pitcher who is way past his prime, Zack Greinke will still be one of top free agents who could aid the pitching rotation of a legitimate contending organization. At 38 years of age, he should not be given more than a two-year deal at the very least, especially with Severino returning and Cole still being one of the best starting pitchers in the MLB. Paying less for Danny Duffy or Drew Smyly would be even more ideal than signing Greinke.

The mistakes of the Yankees organization has been spiraling over the past years, such as acquiring Kei Igawa or Carl Pavano. The continuous issue has derailed the success of this iteration of the Yankees despite the star-studded batting from top to bottom. With several star free agents next season, they must consider deciding to head toward the youth direction as well and adding youngsters as well rather than relying on veterans way too much.

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Andrelton Simmons

Marcus Semien and Corey Seager are two spectacular infielders both heading to the Texas Rangers, while Trevor Story, Freddie Freeman, and Carlos Correa are still three of the three superb names available on the market. The Yankees could definitely afford paying any of these players to bolster their infield depth rather settling for a guy like Andrelton Simmons.

Boone was alternating various individuals at shortstop last season because they had trouble defensively and versatility. The Yankees middle infield were prone to fielding errors, but that would not be the case to add either a phenomenal talent in Story or Correa. Simmons is a respectable talent in the MLB scene, but if the Yankees are able to add a talent like Story or Correa, they should not settle for a shortstop like Simmons. The World Series aspirations of New York is never going to plummet, thus this is a massive opportunity for them to fill in the huge hole on their roster.

The Yankees fans are looking forward for them to eclipse the Tampa Bay Rays and Boston Red Sox in the standings this season, but they must focus on filling in the gaps on their lineup. The Rays and Red Sox were the two squads that eliminated them the past two years because Kevin Cash and Alex Cora knew how to exploit the immense talent the Yankees had on their fold.