In February of 1998, a 31-year-old former intern of the organization took over as the Senior Vice President and General Manager of the New York Yankees.

Since then, Brian Cashman has been the man in charge of the Yankees, holding one of the longest current tenures of GMs in the sport today.

On Saturday, Buster Olney of ESPN hinted in his blog that this may in fact be the final year Cashman could be with the team.

Cashman is in the final year of a three-year deal he signed back in September of 2008.

Some have wondered before the season if Cashman was in fact fed up and tired of the organization, something that came up after the Yankees upper management vetoed Cashman and went ahead to sign Rafael Soriano to a three-year deal.

Cashman may have gotten that one right, considering Soriano has been out on the disabled list since the end of May and at the time, his ERA was over five.

Soriano was not the only player that Cashman was against bringing in and feuded with Yankees management over.

Before the 2004 season, Cashman could have brought in Vladimir Guerrero, who was 29 at the time and recovering from injuries in the 2003 season, which made a couple of teams skeptical about bringing him in.

Instead, the Yankees signed Gary Sheffield, 35 at the time, to a three-year deal for $39 million. Sheffield was known for having a bad attitude and was not the most well-liked person in baseball. But because at the time he still had the superstar name and quality, that made George Steinbrenner personally negotiate with Sheffield and ignore Cashman’s request to go for Guerrero.

Short-term, Sheffield was a very good player, up until he got hurt in 2006. Sheffield missed the most of the 2006 season with a severe wrist injury, which lead to the Yankees trading for Bobby Abreu that summer.

They tried Sheffield out at first base, which he was not for. He also thought he was better than Abreu and was getting to be very disgruntled in the Yankee clubhouse, which lead to the Yankees trading Sheffield to the Detroit Tigers before 2007.

Long-term, Guerrero would have been the smarter choice over Sheffield.

Cashman was also against the Yankees signing Tony Womack before the 2005 season.

These were some of the things that nearly drove Cashman out of the job after the 2005 season. The Yankees upper management were going over Cashman’s head and he nearly walked away from the organization he had been a part of since 1986.

The Washington Nationals were reportedly rumored to be interested in hiring Cashman to be their GM, but Cashman was promised full autonomy from the Yankees and from George Steinbrenner.

Cashman was even quoted to saying, “I want to run this team and not have to wake up one day to see we signed Tony Womack without my knowing.”

Shows how much Cashman really wanted Womack, huh?

In 2005, Womack hit .249 with no homers, 15 RBI and only stole 27 bases. He started out as a second basement, but then was moved to the outfield after the Yankees promoted Robinson Cano in May of 2005.

Cashman’s contract ran out again after the 2008 season, but he was still intent to build a championship team, so he re-signed for another three years.

The next year, the Yankees brought in CC Sabathia, A.J. Burnett, Mark Teixeira, and Nick Swisher and won the 2009 World Series.

The World Series was the fourth championship under Cashman’s watch.

And now here we are, another three years later, with the GM’s contract up and the strong possibility of him moving on.

When Olney talked to rival executives around the league, they got the feeling that Cashman was done with the Yankees and was ready to move on.

Cashman on Friday said he wasn’t going to talk negotiations during the season and didn’t want to discuss his future.

To me, that sounds like someone trying to get around answering it and saying how he feels.

Unless something drastic happens or he has a major change of heart, I think 2011 could in fact be the final year for Cashman.

Mike Axisa of River Ave. Blues gave 50-50 odds on Cashman returning.

I’m not even going that high. I say 20-80 on him staying.

After 14 seasons, 10 division titles and four World Series championships, Cashman has had a very good run.

It could be that he is burnt out, or he just wants out of New York.

If it’s time off from baseball and to get away from things, you can understand. We have all gotten stressed out from our jobs and our bosses. I’m sure working for George Steinbrenner couldn’t have been the most pleasant at times.

But, if he wants out of New York, given Cashman’s resume, I’m sure he’d have no hard time finding another job as a GM in baseball.

This probably won’t be a major issue for the Yankees until the end of October or early November once the season is over.

If Cashman decides to walk, finding their next GM will be an interesting subject come the winter time.

So I will leave it up to you the Bleacher Report community to debate and talk about. Is this it for Cashman after 2011?

Only time will tell. Stay tuned.

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