Several years ago the Red Sox leapt into the Johan Santana sweepstakes, with Santana ultimately ending up on the New York Mets. If Santana had wound up on the Sox, the Twins would have received Jon Lester and others. What's been the track record in the interim?
First, I wrote that among the great pitchers in contemporary baseball history, few have averaged more than 16 wins during the six year career span contemplated...and second, Santana wound up making a king's ransom, which also decreases your ability to pay other players.
During the past three years, the cancer survivor Lester has earned about 5.17 million dollars, and the Mets ace Santana has earned over ten times as much, nearly 56 million.
Sometimes the deals you don't make turn out the best. And the pitcher most similar (similarity scores) to Johan Santana through age 25? Jon Lester.