#21 — Brian Cashman

This post is part of a series in which we count down the 25 best GMs in history.  For an explanation, please see this post.


Of all the successful general managers in history, few are more of a challenge to assess than Brian Cashman.  We could see an argument that he should rate much higher — after all, the Yankees have won six pennants and four championships in his 17 years as general manager, a record very few can match.  On the other hand, he had some advantages: he started with a great team (he won titles his first three seasons), his ownership provided him enormous financial resources (peaking with a payroll 60% more than the second highest team), and there are countless stories of his decisions being overridden by his bosses, at times calling into question who was running the show.

Cashman took over the Yankees in February 1998.  At the time, his team had five great homegrown talents — Derek Jeter, Bernie Williams, Mariano Rivera, Jorge Posada, and Andy Pettitte — all but Williams near the start of their careers and not yet earning free market salaries.  His first team won 114 games, the most in league history.  This excellent (and, for a time, relatively underpaid) core helped allow him to acquire or sign stars or superstars seemingly every year — Roger Clemens, Mike Mussina, Jason Giambi, Hideki Matsui, Alex Rodriguez, Gary Sheffield, Randy Johnson, Johnny Damon, CC Sabathia, Mark Teixeira, Jacoby Ellsbury, Masahiro Tanaka, and more — in order to keep winning.

As time went on, the lack of new homegrown talent led to an increasingly high payroll (not enough value was coming from pre-free agency players) so that by 2014 the team had an old and mediocre roster and Cashman seemed finally to have hit his budget limit. But this was 16 years into the job.  For many years Cashman’s acquisitions, when added to his nucleus, preserved the Yankees as one of the best teams in baseball.

The problem is not that Cashman has not done a fine job — he obviously has.  It’s that no one else in history has ever had a job like it.  There is really no one to compare him to.  Moreover, the complex Yankee front office, with key executives split between New York and Tampa and overseen for the first decade by an active, engaged George Steinbrenner, makes apportioning credit or blame somewhat problematic.  Nevertheless, Cashman was clearly the point man for trades and free agent signings and should be evaluated on his results.

The key to the Yankees undeniable success during much of Cashman’s tenure, certainly for the first decade, was the talent he inherited.  Jeter and Rivera put together Hall of Fame careers, while Williams, Posada and Pettitte were close to that level and contributed for many years.  The great 1998 Yankees were built mainly by Gene Michael (the GM from 1991 to 1995) and Bob Watson (1996-97), who between them held onto the prospects (something the Yankees had not done, to their detriment, in the 1980s).  Michael also made great deals for Paul O’Neill, David Cone, and Tino Martinez, while Watson signed David Wells and acquired Scott Brosius.

So Cashman started with a young core surrounded by veterans.  As the veterans aged out, he generally went out to the market to find replacements.  After losing the 2001 World Series, the Yankees lost O’Neill, Brosius, Martinez, and Chuck Knoblauch from their starting lineup, either via retirement or free agency, but Cashman acquired Jason Giambi (the best hitter on the market), Robin Ventura, Raul Mondesi, and Rondell White.  Like most GMs, Cashman had good luck when he signed the high end guys, which he often did, and less luck with the non-stars.  Once he had to pay his homegrown guys market rate (Jeter made $750,000 in 1998, but $10 million two years later), the team payroll took off.

The Yankees also had less luck with developing talent during the Cashman years, partly because his free agent spending cost the team a lot of high draft picks.  He acquired 22-year-old Alfonso Soriano from Japan in 1998 and the second baseman gave them three excellent seasons (2001-2003) before being used to acquire Alex Rodriguez in 2004.  There was also some bad luck — Nick Johnson was a very highly rated hitting prospect who could not stay healthy.  After losing the 2003 Series with a 101-win team, Cashman signed Gary Sheffield and traded for Rodriguez.   The 2004 team won 101 again, before losing an historic seven game LCS to the Red Sox.

By the mid-2000s, the Yankees spending was far outstripping the competition.  While their 2001 payroll was $109 million, essentially the same as the Red Sox, by 2004 they were up to $182 million (compared with Boston’s second highest $125 million).   The next year they were up to $205 million, $84 million more than Boston.  At this point the Yankees leveled off and other teams began to catch up.   Helping considerably, the Yankees introduced a new star in 2005 when Robinson Cano forced his way into the lineup at second base.  A player as good as Cano, probably on his way to the Hall of Fame, can make up for a lot of bad drafts.

After nine straight division titles, the Yankees finally finished second in 2007 and then missed the playoffs in 2008.  The team had gotten quite old and had holes everywhere.  Cashman went back out to the market and signed the best pitcher (Sabathia) and best hitter (Teixeira), while also picking up Nick Swisher and A.J. Burnett.  Suddenly the Yankees were back in business — Sabathia and Teixeira had great seasons, as did many of their holdover stars, and they waltzed to a 103-victory season and a World Series title.

Although this veteran team hung on for a few more years, winning three more division titles, by 2013 the Yankees were old, expensive (a record $228 million payroll), and no longer contending.  Rodriguez signed a 10-year extension after the 2007 season, a contract the Yankees soon regretted.  Sabathia had three great seasons before he began to struggle with effectiveness and health.  Teixeira battled injuries, Rivera and Jeter retired.  Cashman got a lot of value out of all of these players, but to get them he needed to keeping paying them past the time (except for Rivera) that they were contributing, and the Yankees paid the price in the early 2010s.

As of this writing, it appears that Cashman is passing on the free market this off-season.  It will be difficult to improve the team without increasing the budget, since they already have $180M committed to just 10 players in 2016.  The team has the money, and a GM that has proven adept at finding players to give it to. Still just 47, Cashman likely has a long career ahead of him.

— Mark

(We invite your comments below.)

To read more about the history of baseball operations and the GM, please buy our new book In Pursuit of Pennants–Baseball Operations from Deadball to Moneyball via the publisher or at your favorite on-line store.



19 thoughts on “#21 — Brian Cashman

  1. So, if I am reading this correctly, Cashman inherited a solid franchise built on enormous economic advantage and in possession of incredible momentum. As that momentum died out he leveraged that economic advantage to sign the obvious and get solid productivity as expected, but screwed up on everything that was not obvious. As the economic advantage died out to match the aging momentum, the Yankee fortunes came back to earth and now hover at mediocre.

    Meanwhile, the farm system is in shambles and the team is ancient and the payroll commitments he put into place (on the obvious) remain shackles on flexibility.

    And, for this, Cashman is one of the all-time greats? Man, I wish the bar were that low with MY industry!

    Liked by 2 people

    • Part of what went into our thinking is that it is much harder to maintain excellence over a long period of time than is commonly perceived. There are many instances of teams that appeared destined for a multi-year run that fell back relatively quickly. In our opinion, Cashman deserves some credit for sustaining the run—14 playoff appearances in his first 15 years is quite an accomplishment regardless of the Yankees resource advantages.


    • 1000% agree. Great response. Cashman being on this list is a complete joke(by the way, I am a long timeYankee fan). Virtually ALL OF HIS “GOOD” MOVES arre the result of having the most $ in his checking account or having the ability to absorb a large contract (via trade). He has made no great draft picks in his CAREER—please tell me one. Yes, Iknow Yankees pick late in draft but gee, it seems like St Louis and Boston and others seem to do fine. We have NO ONE in the minors ready to move up except some average prospects. These people give him credit for everything good but give him a pass for any moves (“his superiors” forced him into that move….well you can’t have it both ways). This guy is a disaster yet somehow he is given a pass in the NY media. It is one of the great mysteries in my life: who killed Kennedy? Why does no one criticize Brian Cashman. I love the articles written about him now as if he just got here last year. It is pathetic. He is the GM and is RESPONSIBLE FOR TALENT ACQUISITION-PERIOD. We are in a terrible spot now. Ageing infield, stupid long term deals (oh yeah, I forgot, he was forced into those), ageing pitching staff (which is 100% BOUGHT!), crappy outfield, no farmsystem. Yeah, he is one of the greatest GMs ever. As you said, just inherited a great core and then bought his way to success every year until the system changed. Well know it is timeto see how brilliant you are….


  2. Cashman’s career/report card should be broken down into three parts:

    The Stick/Watson Beneficiary Era (1998-2001)
    The Straw Man GM Era (2002-2005)
    The Full Autonomy Era (2006-2014)

    Based on what’s truly “him” – meaning 2006 through 2014 – placing Cashman anywhere on a list of great GMs is ludicrous.

    Liked by 3 people

    • Credit for that 2009 World Series title goes to the Steinbrenner Family Checkbook – for allowing Cashman to spend $423.5 million over a few weeks time to acquire free agents Mark Teixeira, CC Sabathia and A.J. Burnett – and to Toronto physician Anthony Galea – for juicing A-Rod to the point where he had one of the one of the best overall offensive performances by a single player on a team who won a World Championship in the last 30 years of baseball history (to that point) – if not the best “such season” ever.


  3. Unless you are claiming he was instrumental in drafting the core of the 1996-2000 teams I don’t see how you can justify this ranking. In the last 14 years the Yankees have won one World Series – the same as the Marlins! – with by far the highest payroll in baseball. In fact I’m guessing their payroll advantage over other teams is probably close to their advantage during some of their dynasty years (the 30’s or 50’s). He’s made some good moves but they’ve been outweighed by his disastrous moves – preferring Sheffield over Beltran, signing Teixeira, the ARod extension, Jeter’s extension instead of replacing him. The last three years they’ve had the #1 payroll in baseball but only the 9th best record.


  4. While I’m by no means a Cashman fan, I think it’s worth seeing out the rest of the list before deciding he’s too high at #21. This is the first time I’ve seen a list like this, one that’s this detailed and deep. I mean, as an honest question, is #21 really as great as that? If Cashman shouldn’t have been on the top 25, who would have been #26, and is he really that much better than Cashman? If Cashman doesn’t get any credit because the core was already there and he brought in high-priced vets, does that mean Torre doesn’t get any credit for managing them?


  5. Cashman inherited a great core and a healthy budget, and when the core got more expensive after winning in 2000 and Jeter getting a 10 yr extension, he spent like no other GM in the history of the game for 10 years during which he won exactly 1 championship and allowed the farm system to collapse at the end of this period.

    When Hal reigned in the budget after 2009, and dropped payroll 50 million in payroll adjusted dollars from the 2003-2009 spending levels, the Yankees missed the playoffs 2 years in a row despite a 2nd WC and a weaker AL East. Maybe Hal deserves most of the blame there, but if Cashman is going to get credit for spending Georges money, then so be it

    We will never know how Cashman would have fared under other circumstances, but I think the Yankees made a mistake extending him 3 yrs.


  6. Cashman inherited a great core and a healthy budget, and when the core got more expensive after winning in 2000 and Jeter getting a 10 yr extension, he spent like no other GM in the history of the game for 10 years during which he won exactly 1 championship and allowed the farm system to collapse at the end of this period.

    When Hal reigned in the budget after 2009, and dropped payroll 50 million in payroll adjusted dollars from the 2003-2009 spending levels, the Yankees missed the playoffs 2 years in a row despite a 2nd WC and a weaker AL East. Maybe Hal deserves most of the blame there, but if Cashman is going to get credit for spending Georges money, then so be it


  7. Cashman made a number of good moves not listed in this article. When Pavano and Wright got hurt in 2005, scrap heap acquisitions Aaron Small and Shawn Chacon held the rotation together to win the Yanks the division. In 2014, he got Martin Prado for basically nothing, and has since used Prado in a trade for a 24-year-old pitcher who led the league in fastball velocity. Cashman also acquired Curtis Granderson, who reached new levels of excellence at the plate as a Yankee. Granderson wasn’t the first smart pick-up whose swing would easily take advantage of Yankee Stadium; Johnny Damon earned his contract by hitting more HRs for the Yankees than in any years prior.

    I know there are other useful players Cashman has gotten for next to nothing mid-season, like Soriano in 2013, though a long list of names isn’t jumping to mind. A persistent factor has been the team’s ability to add salary, but still, Cashman has seemed to make the right calls in who to throw that money at.

    As far as his legacy in the history of the GM, I think Cashman’s most noteworthy niche has been in media relations. He’s managed to mix political correctness and ugly truths in the perfect ratio to keep trigger-happy Steinbrenners from firing him and scandal-grubbing journalists from turning his job into a circus. The only person he’s caused public drama with was A-Rod, which is no small feat given the parade of characters through his office in the last 16 years. Along with Joe Torre, Cashman was one of the key figures in bringing professionalism back to the Yankee brand after classless decades under The Boss.


  8. Brian cashman is the luckiest gm ever.his championships were won because of stick and George’s wallet.as noted earlier the only true title he won was when he outspent everybody.he has absolutely no eye for talent.under his leadership our farm system has crumbled. Remember when we had four young up and coming pitchers?hughes,joba,clippard and Kennedy. He kept the wrong two .people forget,the year he signed tex.he couldve signed that guy from florida who went on to sign with detriot.than became the best hitter in baseball.ill let you guess who it was. Than,when every team was throwing studs at us for Montero. Who does he finally get for him?a broke down pineda.how about the time we (dont remember the year)had a high 1st round draft pick?he drafted brackman!a guy he knew was heading to tommy john surgery.last one,Igawa and pavano????!!!!!cashman is the worst gm in baseball.to put him on this list is shameful!


  9. I don’t have any issue with Cashman being on this list. He’s done a great job for an extended period of time. The Yankees have made the playoffs in all but 3 years of his tenure. But I don’t get how Gene Michael is not on this list at all. He basically constructed the team that Cashman inherited. I know that the Yankees only made the playoffs in Michael’s last year (95), but he set the stage for the Yankees dynasty of the late 90’s.


  10. HOW CAN YOU PUT Brian Cashman ON THIS LIST, HE IS ONE OF THE POORER GM’s IN THE LEAGUE THE YANKEES THIS YEAR ARE LOUSY AND THE FARM SYSTEM IS IT’S USUAL……..BARREN !!!!!! he deserves a spot on the list of the WORST GM’S but not the best, nowhere close !!!!!!!!!!!


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