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This post is part of a series in which Mark Armour and Daniel Levitt count down the 25 best GMs in history, cross-posting from our blog. 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 home-grown talents — Derek Jeter, Bernie Williams, Mariano Rivera, Jorge Posada, and Andy Pettitte — all but Williams were 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, 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. 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 publisheror at your favorite on-line store. Click here to view the article

This post is part of a series in which Mark Armour and I count down the 25 best GMs in history, crossposting from our blog. For an explanation, please see this post. [This one is from Mark] Of all the successful general managers in history, few are more of challenge to access 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, 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. 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.