Best all-time general managers: No. 6, Brian Cashman

The next in our countdown of the best all-time general managers has been in his office for 20 years now with the most visible organization in the game.

New York Yankees, 1998-Present

There is a perfectly reasonable impression circulating around the fringes of baseball that the simplest way to build a winning team is by throwing money at the problem. When this view is propounded, Brian Cashman and the Yankees are usually offered as prime evidence. Though, his true excellence is why he’s among the best all-time general managers.

Obviously, Cashman operates at a competitive financial advantage. Having acknowledged that, let it also be noted that many teams often operate at financial competitive advantages. The Detroit Tigers’ 2017 opening day payroll was exceeded by just three teams; they won 64 games. As recently as 2012, the Red Sox parlayed $175 million – the game’s third-largest payroll — into 70 victories. Then they cut payroll by $20 million in 2013 and won the World Series.

As any drunken sailor can tell you, the easiest thing in the world to do is spend money. It is a far tougher challenge to spend it well. Yes, Brian Cashman has been advantaged. He has also been quite skilled.

Cashman’s is a classic “New York boy makes good” story. A metropolitan native, he caught on as an intern in the Yankees front office and worked his way up to become assistant to GM Bob Watson. When Watson retired, Cashman took over. He got fortunate in one respect: He arrived just as age began to mellow the previously meddlesome George Steinbrenner. More than any of the numerous GMs he had previously employed, Steinbrenner got out of Cashman’s way and let him run the show.

What Cashman principally did was identify quality players and then either get or keep them. Here’s a number that drives home the point. Under Cashman, the Yankees have allowed 248 players to move to another big league team via sale, trade or free agency. Only 22 of those 248 – 9 percent — have produced a short-term value for their new team in excess of +1.0. The Cashman Yankees are the star in the baseball firmament; little of use escapes their gravitational pull.

Cashman ranks sixth among the best all-time general managers for total long-term improvement, behind only Barney Dreyfuss, John McGraw, Ed Barrow, John Schuerholz, and Branch Rickey. He has the second-best record among the best all-time general managers in average long-term free agent value and total long-term free agent value. John Day and John Schuerholz respectively lead him in those three categories, and since Cashman is still working he may eventually hit the top spot in one or both of them.

Obviously, inheriting and re-signing Derek Jeter, Bernie Williams, Mariano Rivera and Jorge Posada is a good thing. Also, obviously, Cashman has spent wisely in the open market, as the deals with Roger Clemens, David Cone, Mike Mussina, Hideki Matsui, Gary Sheffield, Johnny Damon and Jason Giambi, among others, demonstrate.

In recent seasons, he has also expanded his footprint on the trade market, as the deals that landed Giancarlo Stanton, Didi Gregorius and Aaron Hicks demonstrate.

The money behind Cashman occasionally disguises his skills. Despite his four World Series wins, six pennants and dozen divisional titles, voters have never named him Executive of The Year. But to merely write off Cashmen’s success as a checkbook function overlooks the fact that he had to be right…and he has consistently been. That’s why Cashman’s Yankees are hard to beat.

Brian Cashman

In the first six categories, values reflect the standard deviation of the GM’s performance above or below the historical mean for that category. Category 7 awards or deducts points for seasons in which the GM’s short-term impact exceeded the margin by which his team either reached post-season or failed to do so. Category 8 represents post-season appearances; in categories 7 and 8 indicated points are based on numbers of teams and post-season berths.

1 Short-term average: +1.00

2 Short-term total: +1.14

3 Long-term average: +1.52

4 Long-term total: +2.27

5 Residual average: None

6 Residual total: None

7 GM’s post-season shares:

• 2012 award +0.38. Cashman aided the Yankees by +7.6 games; they qualified for post-season by 2 games. Key moves: Signed Hiroki Kuroda, +3.4; signed Andy Pettitte, +1.3.
• 2013 penalty: -0.38. Cashman hurt the Yankees by -10.9 games; they failed to qualify for post-season by 7 games. Key moves: Released Nick Swisher, +1.6; acquired Vernon Wells, -1.8; signed Lyle Overbay, -1.5; signed Edward Nunez, -2.6.
• 2015 award +0.38. Cashman aided the Yankees by +2.6 games; they qualified for post-season by 2 games. Key moves: Promoted Luis Severino, +1.4; signed Andrew Miller, +1.8; acquired Didi Gregorius, +1.2.

Category 7 total: +0.38.

8 Credit for post-season appearances (1998, +0.44, 1999, +0.44, 2000, +0.44; 2001,+0.44; 2002, +0.44; 2003, +0.44; 2004, +0.44; 2005, +0.44; 2006, +0.44; 2007, +0.44; 2009, +0.44; 2010, +0.44; 2011, +0.44; 2012, +0.38; 2015, +0.38; 2017, +0.38): +6.86

Grand total: +13.17

That gives you all the information you need as to why Brian Cashman ranks as #6 on our list of best all-time general managers.