At the time of Cashman's hiring, it was still a novel concept that a successful general manager could be someone not strictly from the world of baseball scouting. To hire someone who was smart and organized, who knew to surround himself with competent people and who saw the value in both traditional scouting as well as data-driven analysis required a vision and courage to see things differently.
Besides, Yankees general managers didn't last very long under Steinbrenner. Cashman was his 14th in 25 years, and if Gene Michael and Bob Watson and so many other competent men couldn't please The Boss, what chance did young Brian Cashman have?
Now Cashman is about to begin his 16th Spring Training as general manager in the Bronx, and in the wake of Hal Steinbrenner taking over day-to-day operations even before his dad died in 2010, Cashman appears to have as much power and influence as almost any general manager in the game.
In recent years, Cashman has overseen a transformation of the Yankees' baseball operations. They remain heavily invested in traditional scouting methods but have also embraced the full "Moneyball" analysis. In an interview with MLB Network Radio on Sunday, Cashman said that groundbreaking analyst Bill James' influence on the game has been so profound that he deserves to be in the Hall of Fame conversation.
Cashman -- with Hal Steinbrenner, obviously -- has steered the Yanks away from the wild spending sprees of past years. Instead, Cashman has attempted to construct baseball's best Minor League system. To do that, he needed to be great in terms of scouting, coaching, etc.
"We want Draft day to be the most important day of the year," Cashman has said.
That Minor League system will be critical in the years ahead as the Yankees say they're committed to being under baseball's $189 million luxury-tax threshold by Opening Day 2014.
The Yankees have spent cautiously for a second straight offseason, but due to past commitments, they still have a payroll over $200 million in 2013. As Cashman said, "We're not going to apologize for having money. That's part of The Boss' legacy."
Rather than set the market, he has allowed the market to return to him, landing Hiroki Kuroda shortly after the start of Spring Training a year ago and getting Travis Hafner and Kevin Youkilis in recent weeks.
Cashman's scorecard has not been perfect. He whiffed on Carl Pavano and Kevin Brown, among others, but has still done far more right than wrong. In the past five years, his farm system has produced an assembly line of gifted arms: Phil Hughes, David Robertson, David Phelps, Ivan Nova and Joba Chamberlain.
His 16th season on the job begins at a particularly challenging time. With an aging roster, the Yanks have a smaller margin for error than usual. They need Andy Pettitte and CC Sabathia to stay healthy and for Mark Teixeira, Curtis Granderson and Youkilis to have productive seasons. And they need more of their young talent to start pushing for spots on the Major League roster.
Cashman's legacy is that the Yankees made 13 playoff appearances in 14 years and went to the World Series six years, winning it four times. Money aside, he has made the Yanks' baseball department as respected as any in the game and produced a generation of executives -- Damon Oppenheimer, Billy Eppler, etc. -- who could probably land jobs as general managers if they choose to.
Regardless of how 2013 plays out, Cashman's legacy seems secure. He took over in the Bronx at a time when Derek Jeter, Bernie Williams and Jorge Posada were on their way to defining another era of Yankees dominance.
Cashman -- along with the Steinbrenner family, Jeter and others -- has kept it going. The Yanks have won just one championship the past 11 seasons, but they've been in the mix every year. As legacies go -- and especially Yankees legacies -- that's not a bad one.