MONDAY: The extension is complete, Jon Heyman of FanRag Sports tweets. The pact is worth “$25MM plus” across five years.

FRIDAY: The Yankees are closing in on a five-year contract extension with general manager Brian Cashman that would pay him a total of $25MM, reports USA Today’s Bob Nightengale. Not only would that represent a considerably lengthier pact than the three-year deal Cashman is on the verge of completing, it’d also represent a notable annual raise from his current $3MM annual rate.

The Cashman extension comes on the heels of an extremely successful season for a Yankees club that many believed to be in the midst of a transitional period. Rather, Cashman’s club was buoyed by breakouts from young names like Aaron Judge, Luis Severino and Jordan Montgomery, while more experienced players such as Aaron Hicks and Didi Gregorius took significant steps forward and delivered career years.

The Yankees, of course, are also widely regarded to have one of the game’s best farm systems even after trades to acquire Sonny Gray, David Robertson, Tommy Kahnle and Todd Frazier prior to this year’s non-waiver deadline. The prized farm system is the fruit of aggressive spending on the international market as well as recent commitments to shying away from free agents that come with draft-pick compensation — both of which were directives under the Cashman-led Yankees.

It’s a significant show of faith in Cashman at a pivotal point for the franchise. Cashman made a fairly stunning decision following the team’s loss in Game 7 of the American League Championship Series, not only electing not to re-sign his manager of the past 10 years, Joe Girardi, but also to replace Girardi with a former player that does not have a single day of managerial or even coaching experience, former ESPN analyst Aaron Boone. Cashman has spoken positively about Boone and expressed a firm belief that he’ll be able to connect with players and approach managing with an ability to implement “evolving strategies” in a “progressive” manner.

The Boone experiment will be one upon which Cashman is judged extensively, though it’s also worth pointing out that Cashman’s five-year contract is longer than Boone’s three-year guarantee as the team’s new skipper.

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