The biggest question this offseason has been where will Jon Lester sign. A number of teams have been in the discussion, but its seems to be narrowed down to the Red Sox (former team), Giants, Cubs, and Dodgers. There has also been talk that the Yankees are still in contention.
Lester is expected to make his decision tomorrow, and it could shape the way the rest of the offseason.
— Ken Rosenthal (@Ken_Rosenthal) December 8, 2014
There are two teams in particular that need Lester to be able to compete next season. The first team in the Boston Red Sox, who are lacking the pitching that it will take to win a World Series. The bats are their, but they still are missing an ace and a number two. Boston may also try and trade Yoenis Cespedes back to Oakland for Jeff Samardzija, but I doubt that will happen. Lester called Boston home for almost nine years, and I think that makes them the favorite.
The second team is the Cubs, who just like the Red Sox desperately need pitching if they want to compete next season. Chicago has reportedly offered Lester in the range of $140 million for six years. The Red Sox are thought to be right below that number. If Lester wants the money, he will choose the Cubs. Lester would also have the opportunity to help break the Cubs 106 year Championship drought. The Cubs have ton of potential in their farm system and should be World Series contender for years to come.
The Giants are also a finalist for Lester, but in my opinion I don’t think he will land in San Francisco, but I’ve been wrong before. The Giants are able to afford him, after Pablo Sandoval decided to sign with the Red Sox. San Francisco might be looking for some revenge against Boston. If Lester signs with San Francisco, I think that makes them the favorite to win the World Series again, with ace Madison Bumgarner being one of the best pitchers in the game.
The Dodgers and Yankees are both dark horses, and I highly doubt that Lester will end up with either team.
If Jon Lester wants the money, he will sign with the Cubs. If he wants to play for a team that knows how to win he will choose the Giants or Red Sox. Lester has a tough decision and no matter where he ends up he will be successful.
I think Lester will end up in Chicago, the money and the chance to bring a World Series title to Chicago will be too much to pass up.