Lester Lingering

Free agent LHP Jon Lester visited the Cubs today and all signs point to Lester and the northsiders being a ideal fit for one another in an attempt to turn around the Cubs fortunes. Jon Lester has won two world series championships with the Boston Red Sox, and was one of the earliest drafted players by Boston after the Red Sox ownership changed place nearly 15 years ago. The man in charge of making the decisions at that time is now the one who’s running the show in Wirgleyville. Jon Lester’s career number are: 116-67, 3.53ERA, 1457SO’s, with a 1.28WHIP in 1,596IP. The regular season numbers average out to 16-9 with 196SO’s and 215IP. Looking deeper into his background the Cubs will see glaring postseason numbers which is the reason so many teams are throwing their hats in the ring for Lester’s services over the next what is believed to be a six years at a minimum. In the postseason Lester’s 6-4 with a 2.57ERA in 84IP and 73SO’s to go along with a 1.07WHIP. On baseball’s biggest stage Lester has an unblemished mark of 3-0 with a 0.43ERA in 21IP with 18SO’s to pair with a 0.76WHIP. Add all those numbers up and you’ve got a guy ready to cash in for a huge payday.

The Cubs as mentioned earlier are not the only team vying for his services, but most people think the bidding war is going to come down to Theo’s Cubs and his former employer and Lester’s former team for nine seasons the Boston Red Sox. There are a lot of backstories to this subplot of negotiations, but the relationship between Theo and his former bosses, in particular Red Sox President Larry Lucchino were very public at the end of his tenure, and are seen as the main reason behind Theo’s eventual emigration to Chicago. Theo would love nothing more then to pluck away the guy he opened his career selecting in the 2002 MLB Draft. Unfortunately for Theo, the Red Sox are in far better position to outbid the Cubs for Lester’s return services. The Red Sox have a lot more money than Chicago, and their team is in much better position to return to the postseason then Theo’s new team. The Red Sox are coming off their second last place finish in three seasons and with that comes the need for quick turnaround like in 2013 when they went wire-to-wire to win it all.

The main thing to realize is that if Jon Lester does decide to come to Chicago then Theo will have to go and get Cole Hamels. The process for turnaround will again be kickstarted by years if they can get themselves a top of the line ace to go with their cupboard of middle of the rotation starters. Wood, Hendricks, and Arrieta would immediately be bumped a spot down, and that would give the Cubs a lot more depth then they currently have at the position. Lester would more than likely start a domino effect for Theo to start swinging deals perhaps earlier than anticipated. Cole Hamels would be a wonderful addition to pair with Lester. two big left handed starters who have a plethora of postseason experience would go a long way towards rebuilding the team into a contender. The Cubs have the prospects to get Hamels if they get Lester, and a player like Castro or Russell would anchor any deal.

The issue isn’t whether they want Lester, but is it the right time to start opening up the purse strings, or is it better give the growing process with this young core more time to grow and gel under the tutelage of new manager Maddon. Obviously the Cubs want to win, and Theo said he expects to be competing for a divisional crown next year, but the thought of buying too early could spell doom for Chicago, and the city has waited way too long to take another step back. A perfect example is the blunder made by the Edwin Jackson signing that has set the Cubs back a few years in itself, to repeat that again would an epic miscue.