Brian Cashman is having a bad millennium: no World Series 2002-2008, 2010-2018.

Brian Cashman just completed his 21st season as Yankee general manager: 1998-2018. Almost all of Cashman's success was in his first six seasons. Those Yankee teams appeared in the World Series in all but 2002 and won in the first three. In fact, Cashman's first season as GM resulted in the Yankees winning 114 regular season games and 125 including the tournament.

Cashman became GM in February 1998, so clearly his immediate predecessor Bob Watson deserves pretty much all the credit for that team. Watson should get diminishing amounts of credit for the next two.

Cashman's lone championship team was his only one for years 2001-2018. But even the 2009 Yankee team had these holdovers from the Watson era:
Derek Jeter 1995-2014
Jorge Posada 1995-2011
Andy Pettitte 1995-2003, 2007-2010, 2012-2013
Mariano Rivera 1995-2013

So Cashman doesn't even get full credit for 2009. Gene Micheal was GM when those core four started.

Since the arrival of Babe Ruth in 1920, the Yankees have had these long pennant droughts with these GMs:
1965-1975 (11) Ralph Houk, Dan Topping, Jr., Lee McPhail, Gabe Paul
1982-1995 (14) Gene Micheal, Bill Bergesch, Murray Cook, Clyde King, Woody Woodward, Lou Piniella, Bob Quinn, Harding Peterson, Gene Micheal
2002-2008 (7) Brian Cashman
2010-2018 (9) Brian Cashman

First Yankee GM Ed Barrow(1921-1944), had these three year droughts separated by a WS victory: 1929, 1930, 1931, 1932, 1933, 1934, 1935.

Barrow won these pennants: 1921, 1922, 1923, 1926, 1927, 1928, 1932, 1936, 1937, 1938, 1939, 1941, 1942, 1943.

George Weiss was GM 1948-1960: 1949, 1950, 1951, 1952, 1953, 1955, 1956, 1957, 1958, 1960.

Brian Cashman, GM 1998-2018: 1998, 1999, 2000, 2001, 2003, 2009.

Odds of winning pennant and World Series:

in the old 8 team leagues prior to 1961:
1 of 8, times 1 of 2 = 1 of 16

in three division leagues with wild card (s) since 1996:
1 of 4 times 1 of 2, times 1 of 2 = 1 of 16 for the pennant, times 1 of 2 for the World Series = 1 of 32

So it's easier to qualify for the post season tournament, roughly 1 of 4. But then there are two series to win to become league champion, i.e., to win the pennant. That makes the odds roughly 1 of 16, about the same as to win the World Series when that was the only post season play.

So Cashman getting his Yankee into the World Series in 2001 and 2003 is about equal to Barrow or Weiss winning the World Series. And each of Cashman's four WS winning teams succeeded with odds of about 1 of 32, twice that faced by Barrow and Weiss.

So lets assign points based on that:
- 8 or 16 points for winning the pennant but losing the WS
- 16 or 32 points for winning the WS.

				possible	possible	possible
				points	points	points
	Barrow	Weiss	Cashman	Barrow	Weiss	Cashman
years	24	13	21
possible max	384	208	672
pennants	14	10	6
WS	10	7	4
points	Barrow	Weiss	Cashman
pennant only	32	24	32	8	8	16
WS	160	112	128	16	16	32
total	192	136	160
%possible	50.00%	65.38%	23.81%
	Barrow	Weiss	Cashman