Will Yankees Whiff on Santana?

It is that hole at the top of the rotation, more even than A-Rod's postseason shortcomings, that accounts for the Yankees' recent championship shortfall. And it is why, at this moment, they are regarded as less of a World Series threat than not just the Red Sox (with Josh Beckett in the number one pitching slot), but also the Indians (C. C. Sabathia), the Tigers (Justin Verlander) and the Angels (John Lackey). So it is hard to believe that they would pass on a shot at Santana because they don't want to part with both Philip Hughes and Ian Kennedy, two highly promising but unproven pitchers.

These days top prospects are always available to rich teams in the annual draft, as each year some of the most ballyhooed players slip to the Yankees or Red Sox because so few organizations can and will pay the extortionate signing prices. That's how, in 2005, the Red Sox landed Craig Hansen right out of St. John's—at a Major League price of $4 million for four years. Hansen was regarded as every bit the sure thing that Hughes and Kennedy now appear to be. Just two months later Hansen was in the majors with Boston for a cameo, and he was back the next season, where, in 38 appearances, he was lit up to the tune of a 6.63 ERA. Last season he never made it out of Pawtucket, where he surrendered 58 hits and 32 walks in little more than 51 innings. So little is thought of Hansen now that he doesn't even rate a mention as one of the three, four or dozen prospects the Twins want from Boston in return for Santana.

The Yankees are always many millions ahead of their competition—and will be even further ahead next year with the added revenues from the new digs as well as major mistakes like Jason Giambi and Carl Pavano finally off the payroll. Still, they remain at least one giant step behind the sharper management teams. For years, as "Moneyball" concepts of player development were gaining currency everywhere else around the league, the Yankees plundered their minor league system in return for the most expensive players. And when new measures, like the luxury tax, forced even the Yankees to cap their payroll, the team got caught short.

Now that "win now" seems to be the reigning ethic and most of their competitors are willing to deal away elite prospects, particularly for frontline pitching, the Yankees are clinging to their kids. A prospect couldn't have worked out any better than Hanley Ramirez has at shortstop for the Florida Marlins; all he has done in two seasons is win NL Rookie of the Year in 2006, then follow it up with Hall of Fame numbers: .332, 29 home runs, 81 RBIs and 51 stolen bases. Does anyone think the Red Sox made a mistake trading him for Beckett and World Series MVP Mike Lowell? Apparently the Tigers don't. They just reprised the Boston deal, trading their two best prospects—including a young pitcher, Andrew Miller, regarded as highly as any of the Yankee youngsters—to the Marlins for a very talented starter, Dontrelle Willis, and a slugging third basemen, Miguel Cabrera.

There is certainly some bad history in baseball with giving rich, long-term contracts to supposed pitching aces. And the Yankee kids could, in a few years, turn out to be everything they're cracked up to be. But if Santana goes to the Red Sox, it may not much matter. With Boston's rotation of twentysomethings—Beckett, Santana, Daiskuke Matsuzaka and top pitching prospect Clay Buchholz—the Yankees could be competing for a wild-card spot for the foreseeable future.

The Santanas should never be confused with the Pavanos and other pretenders that have disappointed the Yankees in the past. Santana is a rare bird—think Clemens, Randy, Pedro Martinez—and exactly what the Yankees need to propel them back to the top. That why I and everybody else I know here in Boston hope this time Hank Steinbrenner was telling the truth.

© 2007