2. February 18, 1999 — NYY receives Roger Clemens; TOR receives David Wells, Homer Bush, Graeme Lloyd

Well, you have to give something to get something. But when you look at how everything panned out, Cashman essentially got a steal when he acquired one of the best pitchers of all-time.

Clemens anchored the Yankees’ starting staff when they turned a brutal month of September in a World Series title in 2000, topping their crosstown rivals — the New York Mets — in five games.

He would then go on to win the 2001 AL Cy Young award, winning 20 games against merely three losses.

For the tremendous impact he made, you can make the argument that his years in New York were some of the worst of his legendary career.

Most fans, though, will step back and consider what Cashman gave away, what he got in return, and what the team was able to accomplish as a result. In the process, he kept the powerful presence away from division rivals Boston and Toronto.