The first time I spoke to Brian Cashman it was November of 1996, just after the Yankees had won their first World Series since 1978. Cashman, still subordinate to GM Bob Watson, had represented the Yankees at a round table of New York City sports executives (all the locals were there except the Mets, a last-minute noshow after a miserable season). After the panel discussion, I caught up with Cashman and asked him how the Yankees were going to replace then-second baseman Mariano Duncan.

Cashman disagreed that any replacement was necessary. “He just hit .340 for us,” he said. I replied that it was a soft .340 with no walks, and that Duncan was 33, had been a .260 hitter in his career, and would surely regress. Cashman politely refused to accept my premise. I went away feeling skeptical about the baseball acumen of this apparently minor Yankees functionary, an impression seemingly confirmed the next spring when Duncan’s bat and glove simultaneously reverted to form and George Steinbrenner ordered him benched.

Roughly 15 months after that encounter, Cashman replaced Watson as Yankees GM. Around that time I had the opportunity to have a few off the record, one-onone discussions with Cashman and discovered that he was more on the ball than I had initially given him credit for. Still, with the Yankees currently in the process of affixing blame on their manager for their failure to survive the first round of the playoffs for the third consecutive season, the complicity of their well-liked general manager should be examined as well.

A fair assessment of Cashman is difficult due to the twisted lines of authority within the Yankees organization. As yesterday’s column on the state of Yankees pitching suggested, this recent chapter of team history could be labeled “Why the Yankees Slept.” The team seemed to have been caught by surprise when their starting rotation departed after 2003. After the subsequent failures of Carl Pavano and Jaret Wright to pick up where Andy Pettitte and Roger Clemens left off, Cashman finally was able to focus the team on drafting and developing young pitching.

The fruits of improved drafting will begin paying major dividends as soon as next year, should the Yankees choose to let them, but the damage to the 2004 through 2007 teams was already done. There is reason to believe Cashman would have done so sooner, had the owner only been willing to listen. This is an organizational failure that has lasted through the entire Steinbrenner era and shouldn’t be blamed on one GM.

That said, it’s worth asking how successful Cashman has been in other aspects of maintaining the team. Cashman held the GM’s chair for the 1998, 1999, and 2000 championship seasons. He did orchestrate the acquisition of Roger Clemens, a key in continuing the dynasty, but the lineups of those teams were substantially similar to those that had come before. The core was so good that it would resist large-scale changes until 2002, when Jason Giambi, Robin Ventura, Rondell White, John Vander Wal, and other veterans were brought in.

Even after the turnover began, the team won, at least in the regular season. In part, that was because of the veteran pitching staff that had its aforementioned last hurrah in 2003. Appreciation of those strong seasons must be tempered with the knowledge that they came at great expense. As many teams, including the Yankees in earlier times, have shown, money must be spent wisely if it is to have a positive impact. Ironically, the Yankees were able to spend their way past many mistakes, but often didn’t spend enough. The Yankees have tolerated a good deal of chaff on the fringes of their roster. The 2003 World Series turned on a mistake by Joe Torre, but the 2001 Series was lost in large part because Cashman had sent them into the postseason with a collection of nonentities on the bench.

Until this season, this was all too typical of the Cashman Yankees. It says something that the Ruben Sierras, Enrique Wilsons, Bubba Crosbys, and Tony Womacks of the world tend to disappear almost as soon as the Yankees are done with them. Cashman and Torre perceive value in them (we can’t know which is the bigger dreamer) where little exists and use them too often, exposing the weaknesses that the rest of baseball has already perceived.

Cashman has also struggled to construct a sufficiently deep bullpen over the last few seasons. Relievers are so variable that picking five that are going to be successful in the same season may be the hardest task in baseball. Still, the results of the last several seasons have been so stark that it’s worth questioning whether Cashman has any feel for relievers at all. He has hit on one outside acquisition per season. Internally produced relievers established in the majors by Cashman-Torre prior to Joba Chamberlain: none (and Joba is just passing through on his way to the starting rotation).

During the Cashman years, the Yankees have averaged 99 wins a season and have made the postseason every year. In no way can he be considered a failed GM. Still, that 99-win average is Torre’s too, and if the Yankees believe that another man could have done better, then they should also take a long, honest look at the man who supplied him with the talent.

Mr. Goldman writes the Pinstriped Bible for yesnetwork.com.