What It Would Take for Chicago Cubs to Land Jon Lester This Offseason

Jon Lester will be one of the most sought after free agents this offseason, and the Cubs figure to be right toward the top of the list of potential suitors. Based on his connections to the Cubs front office, he may feel more comfortable going there than some other options. 

A key competitor for him will be the New York Yankees. As always, the Bronx Bombers will want to throw in their bid for a key free agent. However, based on their waiver claim for Cole Hamels, the Cubs have made it clear they're willing to pay big money for an ace. They would have taken on $22.5 million a year for four more years had they acquired Hamels. 

Luckily for the Cubs, acquiring Lester won't require them giving up any prospects. Unlike other pitchers they could go after in the offseason, like David Price and Johnny Cueto, Lester will only cost them money. But he will cost them a lot of money. 

When it comes right down to it, the signing of Lester may come down to the Cubs and Yankees. Jon Heyman of CBS Sports wrote last month that the Red Sox were long shots to re-sign their former ace and that the Yankees and Cubs would be favorites to land the 30-year old. Not much has changed since then. 

When it comes to a bidding war, there's more than just annual salary that can impact a player's decision. If it does, in fact, come down to the Cubs and Yankees, an extra year of contract may seal the deal in one way or the other. It's likely Lester will at least command four years. Should one team be willing to throw in a fifth year, that could land them the ace. 

It's impossible to know what Lester is thinking, but the fact that he knows the Cubs front office well can't hurt. Also, where he ranks money, location, winning situation, etc. in importance will have a lot to do with his final decision. 

What it could take: five years, $110 million and a strong pitch from the Cubs front office.