Should the Cubs take a shot at James Shields?

It’s no secret that the Chicago Cubs will be looking to add themselves a possible Ace starter in their rotation over the Winter – the only question right now is, who could that pitcher be?

You have free agents such as Jon Lester and James Shields who will be at the top of nearly every team’s list. Now the Cubs could be leaning more towards Lester, the former Boston Red Sox left-hander who was dealt with Jonny Gomes to the Athletics’ for outfielder (who should have been a Cub) Yoenis Cespedes at the end of July.

Both pitchers met up in the Wild Card game, resulting in the Royals advancing to the next round to take on the Angels. Shields (1-0, 4.39 ERA) has worked through 11 innings in the post-season and will start Game 1 of the ALCS against the Baltimore Orioles on Friday night.

The 32 year-old right-hander finished the regular season with a 3.21 ERA (Lester 2.46), 81 earned runs, 23 home runs given up, 44 walks, and striking out 180 batters with a record of 14-8 on the year. Shields picked up the start in Game 3 against the Angels, holding the Halos to just two runs in six innings of work that evening to complete the sweep.

Theo and company will more than likely talk to both players’ representatives in hopes of landing a deal with one or the other. You’ll see teams such as the Boston Red Sox, Oakland Athletics, Kansas City Royals, New York Yankees, and the Minnesota Twins will throw in their bids.

According to baseball insider Jon Heyman, Lester returning to the Red Sox appears to be a long-shot which is great news for the Cubs front office. It’s always great to have a back-up plan, especially if you’re doing your very best to make a splash once the free agency period begins.

Kansas City would be crazy not to do everything in their power to not bring back Shields on a long-term deal well worth over $100 million. That’s a contract that the Cubs should have no problem throwing on the table for either player, considering the money they were willing to invest in both Cole Hammels and Masahiro Tanaka.

Lester could end up asking for $150 million as he’s coming off one of the best seasons of his career, but could ask for a little less depending on what the market value is established once the first signing of the off-season is.