It was a blow to the Yankees that couldn’t have happened before the advent of free agency. Herb Pennock and Waite Hoyt teamed together in the Yankees starting rotation for eight years. Lefty Gomez and Red Ruffing were together for 13 seasons.Vic Raschi, Allie Reynolds, and Ed Lopat teamed together for six years.The players had no freedom of movement, so the teammates broke up on only on the Yankees’ say-so. To some extent even age and injury deferred to the team’s desires.

Apparently Carl Pavano never got the memo. On the verge of finally making his 2006 debut, Pavano suffered another “setback.” In Pavano’s case, “setback” can mean anything from a week of rest to a month in traction; at this writing the consequences of his latest feelings of discomfort, if any, have yet to be disclosed. It was already clear that the decision to sign Pavano already ranked as one of the most ill-considered, expensive mistakes in franchise history, but now the saga of Pavano and his various aches and pains has descended to the level of self-parody.

Ironically, had Pavano been cleared to pitch for the Yankees, he likely would have bumped fellow winter 2004–2005 free agent Jaret Wright from the rotation. Wright too counts as an expensive mistake, albeit less of one than Pavano in that he was able to contribute a stretch of effective, albeit truncated, starts at midseason.

It would be wrong to criticize the Yankees too strongly for these signings, even if, in addition to failing to serve their basic function as pitchers they also forced the Yankees to pass on likely 2006 National League MVP Carlos Beltran, who was practically begging to play in pinstripes that winter.The Yankees had seen their entire starting rotation desert them after the 2003 season, and their first attempt at patching had failed miserably. If they panicked in trying to create a new rotation, it was because they lacked better options.

In 2003,the Yankees went to the World Series with a starting rotation fronted by Mike Mussina, David Wells, Roger Clemens, and Andy Pettitte. It was a truly superior group, even a historic one, with a first ballot Hall of Famer, two other pitchers who would win over 200 games in the majors, and another, Pettitte, who may yet surpass the 200 win mark as well. After, Clemens “retired” for the first time.Wells, 40 years old, was allowed to leave as a free agent. Pettitte, also a free agent, was pursued half-heartedly, the Yankees not making too strong an effort to dissuade the southerner from his desire to pitch closer to home. That left Mussina as the only top-flight starter on the staff.

That winter, the Yankees traded Jeff Weaver, who had frustrated the Yankees with his inconsistency and attitude, to Los Angeles for Kevin Brown, a 38-year-old ace who seemed to still have something left despite a long injury history. They traded for Javier Vazquez. Jon Lieber, who had been paid to rehabilitate his arm through the 2003 season, joined the staff, and Cuban import Jose Contreras was given a chance to succeed in the majors.

Just about none of this worked out, including holdover Mussina who struggled with injuries and inconsistency. Contreras was erratic.Vazquez started out well but his season crashed amidst repeatedly denied rumors of injury. Brown’s body quit on him. Only Lieber was a positive surprise.A total of 15 starts, about half a season’s worth for a fulltime starter, were spent on Tanyon Sturtze, Brad Halsey, Donovan Osborne, Jorge DePaula, and Alex Graman. By season’s end the Yankees had brought back Orlando Hernandez and traded Contreras for Esteban Loaiza. It was this patchwork staff that self-destructed in the American League Championship Series against Boston that fall, choking a three games to none lead and propelling the Red Sox on to their first championship since the world was young.

Free agent pitching classes have been thin in recent years. Even when a top name makes it to the open market, they carry more than their fair share of question marks. This was the case with Pettitte, whose arm had been an injury waiting to happen for years — the Yankees guessed correctly there, as Pettitte missed half the 2004 season. Last winter, A.J. Burnett was typical of the breed, a pitcher with terrific stuff and occasionally strong results who seemed to spend as much time on the disabled list as he did on the mound. The Blue Jays bit and reaped some good pitching — and even more DL time.

The top three pitching free agents in the winter of 2004-2005 were Pavano, Wright, and Matt Clement. Based on durability alone, Clement seemed the safest pick at the time. He had made at least 30 starts every season going back to 1999. He was inconsistent but had generally been above average, and many a baseball mind thought that with the right handling, in an organization more progressive than Chicago, he might blossom.

Wright and Pavano were, of course, one-year wonders, pitchers who had been highly regarded at various times but couldn’t stay out of their own way long enough to build up any kind of résumé. Both were atypically healthy and effective in 2004, then hit the market for their payoff.

The Red Sox signed Clement and have received one good half-season in a year and a half of work. The Yankees haven’t received even that much from Wright and Pavano. It turned out that the correct answer was “none of the above,” but with the rotation in tatters, the Yankees felt they had little choice but to gamble.

With yet another weak free agent class in the offing, the lesson to be learned is that the path to good pitching is to build strong, deep minor league systems that provides a team with some measure of quality and quantity. Failing that, there will be more Pavano’s to come, leading to more midseason Loaiza’s and Cory Lidle’s, leading to more frustration — and still more Pavano’s.

Mr. Goldman writes the Pinstriped Bible for www.yesnetwork.com and is the author of “Forging Genius.”