Best Cy Young finish: Fourth (2010)
If Jon Lester retires having never won the Cy Young award, he might go down as one of the most disappointing pitchers in history. Every year without fail, fans, analysts and pundits pick Lester as their AL Cy favorite. Yet, he's received votes for the award just once.
It's practically guaranteed that people will pick him again this season and while he has never really close to the award, there's good reason to think that this is his year.
In each of his last four seasons, he's won at least 15 games, had an ERA better than 3.50 and had a WHIP around 1.20. He's also struck out 225 batters twice. Lester is a great pitcher. He may still be on the outside looking in when it comes to being elite, but only just.