For several reasons, the Cubs are clear favorites to land Lester this offseason, and he's a player who could make them contenders next year.
Ken Rosenthal of Fox Sports has gone as far as to say that Lester's own teammates believe he will sign with the Cubs in the offseason. He states in the accompanying video:
Some of Jon Lester's former teammates believe the southpaw will sign with the Cubs this offseason. Lester, of course, has ties to [president] Theo Epstein and [GM] Jed Hoyer, and the Cubs’ recent waiver claim of Cole Hamels indicates that the team is prepared to spend big money on a top-tier starting pitcher.
Rosenthal brings up two other key reasons why the Cubs might be Lester's top option this offseason. First, he brings up his ties to Epstein and Hoyer, whom he dealt with in Boston.
All other things being equal, which team is Lester going to sign with: the Yankees or the Cubs? The Yankees are a team he's been trained to hate over the years in Boston, and if the Cubs are offering the same amount of money, why sign with the Bronx Bombers? After all, the Cubs are close enough to contention that any doubts about their future shouldn't be a problem to free agents anymore.
The second and possibly more important point that Rosenthal makes it that the Cubs have already shown they're willing to spend big money on front-line pitching. First, they were in on the Masahiro Tanaka sweepstakes this past offseason. Then they put in a waiver claim for Philadelphia's Hamels, who is still owed $22.5 million a year for the next four years.
The fact that the Cubs went in for those two pitchers means they should be all-in for Lester as well. As a lefty ace, Lester is actually more valuable than either of the other two pitchers the Cubs have bid on so far. Tanaka is already dealing with elbow issues, and Hamels is further past his prime than Lester.
If he's their big signing in the offseason, this is how the Cubs rotation could look in 2015:
- LHP Jon Lester
- RHP Jake Arrieta
- LHP Travis Wood
- RHP Kyle Hendricks
- RHP Edwin Jackson
With a rotation like that and a lineup likely to get stronger with the additions of Kris Bryant and Jorge Soler as well as Javier Baez and Arismendy Alcantara playing their first full seasons, the Cubs could be a surprisingly competitive team in 2015. The rebuild is ahead of schedule.