The Boston Red Sox took a terrific risk on non-waiver trade deadline day, dealing future Hall of Fame left fielder Manny Ramirez to the Los Angeles Dodgers as part of a three-way trade with the Pirates that brought two-time All-Star Jason Bay to Boston. Few organizations, particularly one with as rabid and frequently disappointed a fan base as Boston’s, would risk the inevitable backlash that would come with finishing just short of a playoff berth having dumped a 500-home-run man with a lot of life left in his bat.

Theo Epstein and Boston have gone down this road before. On July 31, 2004, the Red Sox traded one of the “holy trinity” of American League shortstops, Nomar Garciaparra, to the Chicago Cubs in a four-team trade that netted them Doug Mientkiewicz and Orlando Cabrera. Garciaparra was hitting .321 AVG/.367 OBA/.500 SLG at the time, but the Red Sox correctly concluded that he had become so fragile that a more reliable shortstop had more value to them, even if he was certain to be less potent offensively. “Nomah” was a Boston icon, but Boston gambled and won, ending the so-called Curse of the Bambino with their first World Series win since 1918. The Ramirez deal represents another throw of those same dice.

For the Yankees, currently looking up at the Red Sox in the American League wild card race, the deal represents a small break. Bay is roughly 80% the hitter that Ramirez is, though it remains to be seen if he will get a boost playing at Fenway Park. Even so, the Sox are probably taking a small hit on offense while making no great change on defense, Bay not being much more of a defensive outfielder than Ramirez was. There are also small but important differences of style. Bay is less patient than Ramirez, more prone to striking out. Ramirez is also one of the best pressure hitters in the game today. Though Bay doesn’t exactly wilt in clutch situations, the gap between his hitting and Ramirez’s is the same as the overall gap between them, which is the difference between a Hall of Famer hitter and one who is merely very good.

While the Yankees should get a small break by pitching to Bay instead of Ramirez, in the wider arms race with Boston they were outmaneuvered, partially due to differences in organizational depth, partially through the sheer audacity of Boston’s front office. With two Pirates outfielders on the market, the Yankees managed to acquire the inferior player, Xavier Nady, a run-of-the-mill-hitter who was having a career year, at least for the Pirates — whether he continues to play over his head as a Yankee remains to be seen, though the returns of his first five games have not been encouraging. That left Bay available for the Red Sox or Rays, who played tug-of-war over the slugger before Boston finally won out.

Boston had to bring in a second team in order to spring Bay and rid themselves of Ramirez. First the Marlins, which floundered on which prospects the Pirates would have received, then the Dodgers, who contributed a potential B-plus-grade third baseman in Andy LaRoche and an intriguing Low-A righty pitcher, Bryan Morris. Though the Pirates probably did not acquire any future MVP or Cy Young candidates, they did get three 24-year-old, major league ready players, two of them position players, a far more solid investment for a rebuilding team, position players being far more reliable.

The Yankees, with a farm system skewed almost entirely toward pitching, couldn’t have constructed that kind of package on their own, and of course, they had no Manny-level star with which to entice another contender into the deal — or did they?

Remember, in 2004 the Red Sox triumphed by taking an inconceivable risk, trading the popular Garciaparra at a point when they were just one game behind in the wild card race. They’re at almost the exact same point now, one game up instead of one down. In both trades, Nomar and Manny, Epstein and colleagues were willing to think the unthinkable. Despite Garciaparra’s tendency toward injury and the many provocations of Ramirez, these players were still quite valuable, and acquiring equivalent talent would be impossible.

The Dodgers didn’t need Manny Ramirez as much as they needed a shortstop. Imagine the possibilities available to the Yankees, if they had been willing to think as the Red Sox do, and consider everything. What could the Yankees have gotten if they were willing to trade Derek Jeter?

Mr. Goldman writes the Pinstriped Bible for yesnetwork.com and is the author of “Forging Genius,” a biography of Casey Stengel.