Brian Cashman certainly comes with a long track record, having held this role since 1998; making him the third-longest tenured GM in baseball behind Brian Sabean and Billy Beane. In that time, the Yankees have been the most consistently successful team in Major League Baseball by almost any measure; four World Series Championships, six American League pennants, twelve AL East division titles, fourteen postseason appearances and an average of 96 wins a season.
Holding on to a GM position for this length of time is impressive, even before accounting for in the unique challenges and expectations that come with the New York Yankees. Cashman hasn't stuck around by being risk-averse either, having been willing to make some big moves (and non-moves) as well as increasingly showing a willingness to publicly distance himself from decisions made over-his-head by the Steinbrenners and president Randy Levine. Even so, it's not always clear to us fans which moves are Cashman's decisions and which are ordered from above. Of course, ownership should have had a much greater visibility of this when deciding to extend Cashman. Still, at very least he has served as a key advisor on all roster moves, and has likely made many of the key decisions; especially since 2005 when he negotiated for more autonomy. Brian Cashman has to receive a lot of credit for the Yankees consistent success since 1998.
Of course, whenever the conversation shifts to Yankee success, its impossible to ignore the uneven financial playing field in baseball. Mostly because it will be brought up. A lot. Sometimes in an angry voice or all-caps typing. Certainly though, there is fairness to the argument, in Cashman's time as GM this franchise has consistently spent more on player payroll than any team, only recently being superseded by the Los Angeles Dodgers. It's increasingly obvious that spending is not the sole key to success, as in 2013 more teams made the postseason from the bottom-6 payrolls (4) than the top-6 (3). This is not a one year event either; the 2014 graveyard of expensive losers includes these top-8 payrolls:- Phillies, Red Sox, Rangers and quite possibly the Yankees themselves. However, there is no doubt that larger payrolls brings advantages; it makes it easier for a team to keep its own talent, to add free-agent players and to survive bloated years on albatross contracts.
The financial strength of the Yankees has allowed Brian Cashman to be a big player in free-agency. Rather than hold him somehow accountable for this advantage by expecting a World Series every year, it seems more prudent to simply consider the moves he has made with the money. For the most part Cashman has used free-agency well. From the signing of Mike Mussina in 2000 to bringing in Masahiro Tanaka in 2013, the Yankees have continuously added top-flight talent through the open market. For the most part, these major signings have gone well, aside from the inevitable decline years - hello Jason Giambi. Moves like signing Johnny Damon, Hideki Matsui, CC Sabathia, A.J. Burnett and Mark Teixeira were all factors in the 2009 World Series win. There have of course been unmitigated disasters like the Carl Pavano and Kei Igawa signings but it's difficult to fault the logic too much on Pavano at least.
It's difficult to talk about non-moves in free agency, it implies that the Yankees should be in on every free-agent. The exception to this in my mind is when the Yankees lose a player of their own who they seemingly could have chosen to keep if they matched the market. The two that stand out here are Andy Pettitte in 2003 and Robinson Cano in 2013. Pettitte leaving did hurt the team but he was brought back to help the team win another championship, however it seems unlikely that Cano will be acquired again; any time in the next ten years it would have to be via trade. After the Alex Rodriguez contract in 2007 (have to pin that one on Hank), Brian Cashman seemed unwilling to commit to another deal that keeps an infielder here into his 40's. The decision to give the bulk of the money to Jacoby Ellsbury on a seven year contract instead will likely be one of the biggest Cashman has made in his time here, regardless of how it turns out.
Cashman hasn't shied away from making the big trade. The biggest in his time here was likely swapping Alfonso Soriano and Joaquin Arias for Alex Rodriguez and a chunk of cash. This was a great trade, though Cashman lucked out when the Texans chose Arias over an older, less polished defender named Robinson Cano. Acquiring Nick Swisher in a package headlined by Wilson Betemit was another move that helped the Yankees win the 2009 World Series. Obtaining Roger Clemens for David Wells was another positive deal.
The Curtis Granderson trade was likely the biggest win-win-win move Cashman was involved with; the Yankees gave up quality talent in Ian Kennedy and Austin Jackson but Granderson lived up to expectations in his time here. The biggest mark against here was probably giving up Mike Lowell, but he loses points for all 3 trades involving Javier Vazquez, including the one where he was traded for Randy Johnson. There have been a few quality players like Tyler Clippard given up for relative peanuts, over the years just as there have been useful players acquired cheap like we've seen this July. Not surprising when he's been making moves for a time-period spanning four full US Presidential terms.
Acquiring Michael Pineda for Jesus Montero represented one of the biggest risks in terms of future perception, but it was the right move at the time given that he was trading from the position of strongest organisational depth and acquiring one of the most valuable assets in baseball; a young, talented, cost-controlled pitcher. At this point, the trade looks like a Cashman win but it has of course flipped several times over the years.
While we're on the subject of organisational depth, it's time to look at the Yankee record with bringing up players from the farm during Brian Cashman's time as GM. Unfortunately New York has not been very successful here recently, which has been a big part of the reason why Cashman has had to make so many free-agent signings and high-profile trades. The talented core that won four World Championships in five seasons at the turn of the millennium - players like Bernie Williams, Derek Jeter, Andy Pettitte, Mariano Rivera and Jorge Posada - were brought into the system during the stewardship of Gene Michael.
Since then, the only home-grown position players to make a major impact at the big level for the New York Yankees have been Robinson Cano and Brett Gardner. As for starting pitchers, Chien-Ming Wang had a brief but successful run with the Yankees, Phil Hughes showed flashes while with the Yankees and Ivan Nova looked like he might have promise before going down to Tommy John surgery. However, the Yankees have not developed a consistent upper-rotation starter since Pettitte.
Of course, the pressure for immediate results has not helped with this, with multiple prospects being traded away for (or blocked-off by) veterans. Still, it's been ten years since Brian Cashman pushed for greater organisational control and seemingly brought a more long-term vision to player development. We still have not seen the results of this and while the farm system has had a positive 2014 by all accounts, much of the talent is still years away and may never make it to the majors. Robert Refsnyder and Jacob Lindgren are the only prospects expected to challenge for a spot with the big-league team out of spring training.
When one person serves as GM for as long as Brian Cashman has, a few hiccups are inevitable. Most of his signings and trades that didn't work out were only flawed with hindsight, and it's often hard to quibble with the logic behind his decisions.
If he does stick around though, I'm hoping the recent improvement in the Yankee farm system continues and we start seeing a steady pipeline of internally developed talent making their way up to the Bronx. With the financial advantage of the Yankees being eroded by a combination of increased wealth elsewhere, additional punitive measures for large payrolls, and a tendency of teams around the league to extend their players before losing them to free-agency; New York cannot continue to compete without developing quality players in-house.
What do you think of Brian Cashman's time here? Here is a list of all moves made while Cashman's been the GM of the Yankees, if you'd like to take a journey through recent franchise history.