It’s been two decades since the two seminal division races run by the Yankees in 1985 and 1986 were lost because the team’s general manager, Clyde King, couldn’t pull the trigger on a necessary deal. The trading season scenario for the 2006 season is shaping up to be like that of those years — deal or die.

In 1985, the Yankees fielded a stacked offense that featured MVP-caliber seasons from Don Mattingly and Rickey Henderson, but the team was undermined by a starting rotation that was two or three deep at best and Bobby Meacham, a shortstop who failed to perform on either side of the ball.When the Yankees met the front-running Blue Jays in September standing three games out with three to play, they had no choice but to start the erratic Eddie Lee Whitson and the wild Joe Cowley against Jimmy Key and Doyle Alexander. It didn’t work out.The Yankees lost the title by two games.

The shortage of pitching had been obvious throughout the season, but the Yankees couldn’t make a deal. The best they could achieve was the too-little, too-late post-deadline acquisition of Joe Niekro from the Houston Astros for Jim DeShaies and two players to be named. On August 1, Bert Blyleven had gone from the Indians to the non-contending Twins for three prospects.

The following year, the problems deepened. The starting rotation was still burdened by Niekro and Whitson, the bullpen had taken a step backward, and shortstop was still a weeping wound. The club had attempted to address the rotation during the off-season by acquiring Britt Burns from the White Sox. Burns had a chronic hip problem, well known at the time, that ended his career before he pitched even a single game in pinstripes.

Unfortunately, the club couldn’t quite figure out how to reload after that misjudgment. They signed 43-year-old Tommy John in May and got good results, but he made only 10 starts. A major trade with the White Sox brought utility infielder Wayne Tolleson, who played just well enough to make shortstop a net positive, but the thing that was really needed, a top starter, remained out of reach. In June, the Red Sox acquired Tom Seaver from the White Sox for the rockbottom price of Steve Lyons. The Yankees hung fire.The finished second that year, 5.5 games behind Boston.

The Yankees didn’t have the benefit of the wild card then and they likely don’t have it now. With the Tigers on a pace for 109 wins and the White Sox right behind them, the Yankees will have to play like their 1927 ancestors to catch up. Outdoing the Red Sox for the division title seems like a more realistic goal, especially with a five-game series at Fenway Park in mid-August and a three-game set in the Bronx in mid-September. As long as the two teams stay close, anything is possible.

It’s not just the schedule that makes the Red Sox vulnerable. Their starting rotation is still a question mark. Curt Schilling will have to bear up after a heavy first-half workload. Josh Beckett has been inconsistent. Jason Johnson was just sent to the farthest minor league reaches to see if he can remember how to be a pitcher.The possible loss of Manny Ramirez to a bad knee would be a blow that the Sox would be unlikely to recover from.

The Yankees have problems as well. Outfielders are needed. The Yankees can’t bet on Hideki Matsui or Gary Sheffield coming back in time to help the club, and there is also the Shawn Chacon Memorial Rotation Spot to fill. With ace pitchers unlikely to be available or affordable, the latter problem will be difficult to address.

Fortunately, as much as baseball tradition says that pitching comes first,all the actual rules of baseball require is that you score more runs than you allow. Because winning 10–9 every night is stressful and time-consuming, most teams would prefer to win 5–3. But in an environment in which bats are more plentifully available than pitching, it makes more sense to try to win by adding runs than by grasping at ways to take them away from the opposition.

The Philadelphia Phillies, who are rumored to have made several expensive contracts available, may be the Yankees’ best bet for one-stop shopping.As well as Tom Gordon has pitched, his contract takes him into his 40th year. This is a risky indulgence no longer worthwhile for a non-competitive team. For his part, Gordon has undergone a sea change from, “I had to get out from under Mariano Rivera,” to “I would love to be Rivera’s doorman again.”

Both of GM Pat Gillick’s corner outfielders are available and would be in demand but for certain limitations, among them enormous contracts and the perception of attitude problems.Pat Burrell will make $27 million over the next two seasons, an investment that any club but the Yankees would find difficult to justify between his lack of defensive ability and a bat that might wilt if removed from Philadelphia’s generous ballpark. Bobby Abreu’s skills are more likely to translate to another venue, but his contract is even more expensive than Burrell’s, with $31 million due over the next two seasons.

Sheffield’s 2007 option is worth $13 million, so if Abreu were to replace him, the Yankees would be adding only $2 million for next season. In Yankees dollars, that’s chump change, especially if it pushes them toward the added revenue that October brings.

Gillick may have to accept some of Brian Cashman’s B-grade pitching prospects like Steven White or Tyler Clippard. Few other clubs can justify that kind of expense, so the field should be open.

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