Cashman's routes go even deeper than just 1998, as he started with the team as a 19-year-old intern with the team back in 1986 and worked his way up through the organization and eventually, got promoted to the Senior Vice President and General Manager job in February of 1998, a position he has held since.
After 15 years on the job though, has the wear and tear gotten to Cashman? Has the everyday grind of New York taken its toll on the 44-year-old, who at times, doesn't seem like he enjoys his job, like for instance; he wasn't in favor of trading a certain prospect to land Alfonso Soriano back in July, but got overruled by his superiors on the deal. And you can even go further back to January of 2011, then again, Yankees upper management again overruled Cashman and signed closer Rafael Soriano to a three-year deal; a deal he ended up opting out of after two seasons.
But Cashman has been used to that sort of thing while as the general manager of the Yankees, but he was more used to it when late-owner George Steinbrenner was still in charge; something that nearly drove Cashman out of town back in 2005 and almost into the arms of the Washington Nationals, but the team promised him more authority to do his job and he stuck around and ever since, has signed three contracts and is currently in the midst of a three-year deal he signed at the end of the 2011 season.
Back in August, there were reports of Hal Steinbrenner getting fed up with the Yankees lack of player development from the minor leagues, something Cashman has had full control of since 2005, in which the Yankees current owner was going to start holding people accountable for if the team didn't start properly developing MLB-ready players to the team.
With one year left though on his current deal, could Cashman be getting a little tired, which Nick Cafardo of the Boston Globe reported after talking to people around baseball on, as the Yankees GM could see other job opportunities around the league if he were to resign before the end of his deal.
If Cashman were to walk away, the first two obvious choices for the job are Damon Oppenheimer; the Yankees director of player personnel and Billy Eppler, the assistant General Manager of the Yankees. You could even throw Jim Hendry's name in there as well, as he is the special assistant to Cashman with the Yankees and served as the general manager of the Chicago Cubs from 2003-2011 before being replaced by Jed Hoyer.
Cafardo mentioned that if the Los Angeles Angels general manager spot opened up, that could be a potential landing spot, or if the Philadelphia Phillies ever decided to let Ruben Amaro, Jr. go, that could be another potential landing spot for Cashman, if he truly wanted to leave and look for work elsewhere, which he'd find in a heartbeat given his resume.
After 15 seasons at the helm, you could see where Cashman might get a little tired or burned out from the job, especially since who his bosses have been for over 20 years, and you would have to think that getting overruled on roster moves might eat away at someone, especially when they were told that they have control of the team. So if it doesn't happen this offseason, where Cashman again is under contract for one more season; it wouldn't be shocking to see him look elsewhere in 2015 and the Yankees could be lead in the future under a new voice and direction.
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