[This series intends to introduce you to each of the legitimate Chicago Cubs GM candidates, and give you a quick, clean rund0wn of the most important information to know about that candidate as the Cubs’ search process continues.]

Name and Age: Brian Cashman, 44.

Current Role and Contract Status: New York Yankees General Manager since 1998, signed through 2011. He currently makes $2 million per year, but that’s sure to go up.

Previously on BN: Way too early short list, Tom Ricketts loves Cashman, Bullets, More Bullets

Record in Current Role: The Yankees have the made the playoffs every year under Cashman except once, and have won the AL East 10 times. They’ve also won six AL Pennants and four World Series titles. They are, after all, the Yankees.

Notable Prior Experience: Cashman is a Yankee lifer, having started with the organization as an intern in 1986 while he was in college. By 1998, he’d worked his way up the ladder to GM.

Reason(s) for Including as Candidate: Big market GM, very successful, and is a “free agent” at the end of the year.

Tom Ricketts’ Criteria: Track record of success in a winning organization? Check. Demonstrated commitment to player development? Check. Strong analytical background? Check.

Pros/Hype: His teams win. He handles the pressures of New York with aplomb. He has an eye for which top talent is worth paying top dollar to acquire, and the Yankees’ farm system is perennially in the top 10 in baseball. Money plays a part in that, too, but it all starts with the man in charge.

Cons/Cynical Criticism: The Yankees were likely to win with a $200 million payroll no matter who was choosing the players. Cashman has never demonstrated that he can win with less than that behemoth budget. (Then again, as the Cubs of recent years have proved, outspending your competitors alone does not a winner make.) There’s also a timing problem. The Yankees are going to make the playoffs, and, if they make a run, it could be a long time before the Cubs would even get a chance to speak to Cashman. Indeed, the Cubs might wait him out, only to find he isn’t interested.

Desirability: Very high. I get the cynicism – I really do. But I think some of the cynics don’t fully appreciate how much pressure Cashman faces from the owners, the media, and the fans in New York. He’s working to please seven different layers of audiences with, at times, competing agendas, and he’s proved that he can do it. The money, of course, helps. But not everyone is cut out to manage a $200 million budget, either. Spending is one thing; spending wisely is another. And Cashman has, by and large, spent wisely in his time with the Yankees. Does anyone truly believe that, if Jim Hendry were handed a $200 million budget, the Cubs would have made the playoffs 12 out of 13 years? I don’t.

Likelihood/Probable Outcome: Most sources believe Cashman has no intention of actually leaving New York. He may be mildly perturbed by some of the Steinbrenners’ decisions, but he’s well-supported, well-compensated, and he’s in his hometown. It’s possible he’ll go as far as an interview with the Cubs, but I have a hard time seeing him taking the job, rather than simply using it to get a little more green from the Yankees.

  • lancealot03

    Didnt make the playoffs in 08…

    • http://www.bleachernation.com Brett

      Yeah, there was supposed to be an “except” in there. Thanks. Will update.

  • Cheryl

    Whoever the new GM is, can he or she get Duncan as pitching coach? I’d also favor Brenley or Girardi as manager. Still feel it’s too soon for Sandberg.

    • hansman1982

      I would love to have Sandberg as Manager with Brenley as Bench Coach

  • hansman1982

    “But not everyone is cut out to manage a $200 million budget, either. Spending is one thing; spending wisely is another. And Cashman has, by and large, spent wisely in his time with the Yankees.”

    This is what scares the shit out of me with Friedmann – sure he has built a helluva team from within but his budget for FA acquisitions would triple and who knows how he would respond when the fans expect to keep a player like Castro rather than get draft picks…

    • Toosh

      Your first 2 sentences describe Hendry to a T.

      • hansman1982

        First two sentances are from Brett…

        I agree though, its one thing to spend ANY amount of money – its a whole different ballgame to spend it wisely. I am just worried that the pressure to keep the Carl Crawford’s would cause Friedmann to operate outside of his “area of expertise” and spend poorly.

  • Jeff

    Almost all of Cashman’s big money moves have panned out, and the ones that haven’t have been supplemented with talent from within the organization. He has a pretty good record on draft picks and international free agents. He handles the media well, and the pressure from being the Cubs main guy wouldn’t affect him, which is one of his strongest attributes in my opinion. He’s been consistent, he has proven to be frugal at times, and he’s not afraid to speak his mind on ownership influenced acquisitions, which was one of the major downfalls of Hendry. A lot of people think Epstein is the perfect guy and many other have fallen in love with Andrew Friedman. Personally, I think Cashman is far and away the best candidate for the job. I hope the Yankees get swept out in the first round, Ricketts isn’t going to waste any time getting someone in place.

    • hansman1982

      And he was around during the creation of YES – Cashman and Epstein are my #1A and #1B right now with Cherington 2 and Friedmann 3.

    • EQ76

      Agree.. i do believe with a 200 mil. budget Hendry would have gotten us there a couple more of the years he was there… like say, 2004 & 2009 when we were still over .500..still not the success rate Cashman has had.. either way, Cashman has the confidence and ability to handle the job, if anything, change the organization’s attitude towards winning.

      With the Yanks, the expectation, much like with Charlie Sheen, has been WINNING!   we need that type of attitude from the top down.. with our fanbase, payroll, etc. there should be no reason why we aren’t competing every year for a playoff spot and I would expect that if a guy like Cashman was in charge.

  • Fishin Phil

    While I think he would do a great job with the Cubs, I agree that he probably is not going to leave NY.

  • die hard

    good summary but I think a $200M budget is not doable….If GM gets a $150M budget, he should be happy….too many other things to do to turn around franchise that will cost lots of money is my take

  • cubbylair

    I’ll make a case for Cashman although there is a residual bias in my thought process. As most remember the last time Cashman’s contract came up for renewal he was promised “total” control. That hasn’t happened as the Tampa faction has continually involved itself with baseball matters. This is the first time Cashman’s contract has come up for renewal under the “official” Hal Steinbrenner regime. Will Cashman show the Same loyalty to son as he did to father?

  • Baseballet

    Cashman’s interest level will really depend on if he’s interested in lording over a rebuilding process.  He would not be getting another ring with the Cubs for a while.  If the Cubs handle the team Tribune-style and sign expensive band aid free agents, they might challenge for their weak division in two years.  But I don’t think Cashman would be interested in short cuts and the Cubs’ traditional cycle of mediocrity.  To build a real World Series caliber team the right way he’d have to be okay with a few bleak seasons.

  • Chris

    Great write up Brett, looking forward to the rest of the candidates

    • http://www.bleachernation.com Brett

      Thanks, Chris. I plan to go through at least the most-likely/discussed guys. The only caveat, of course, is if the Cubs make a hire before I can get through them all…

  • Macho Man

    Whoever ends up taking the GM position, he should understand that the paying audience wants thrills now, not a promissory note for thrills three seasons in the future.  Imagine a movie studio telling its customers, “Well we can’t afford Bruce Willis bareback riding a 747 killing terrorists with a rocket launcher now; however, we can afford Jonathan Gordon Levitt riding a scooter scaring hoodlums with a fake pistol, and if you buy a lot of tickets for that, then maybe we could get…”  Icksnay on that!  If you think the regular fans are cranky now,  imagine when they show up to the ballpark and see a renovation project on the field.  The Cubs will have to pipe music into Wrigley – to drown the sound of the crickets.

    • http://www.bleachernation.com Brett

      I can’t decide if calling him “Jonathan” Gordon Levitt, as opposed to Joseph Gordon Levitt was a part of the joke or just a mistype. It made me chuckle either way.

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