Cubs target Jon Lester

What do the Chicago Cubs do if they strike out in free agency?

At the time of this writing, we’re not too deep into the 2014-15 Major League Baseball offseason quite yet. The Winter Meetings have yet to transpire. There are still multiple marquee free agents available out on the market, and still major trade chips that have yet to move. However, for the Chicago Cubs, it would appear that the clock is ticking on their opportunity to make something of the winter.

The provocation of this line of thought is the result of multiple reports that Jon Lester could be headed back to the Boston Red Sox as a free agent in the very near future. While this has yet to come from a nationally syndicated writer, the whispers will likely confirm what many had already seen as a very likely scenario. Should the Sox sign Lester, it will follow their signings of Pablo Sandoval and Hanley Ramirez, neither of which the Cubs were interested in, but still significant adds nonetheless.

As a result, the Cubs will have to shift their attention to the likes of Max Scherzer and James Shields. They haven’t been heavily connected to either through actual reports, but mere speculation prior to the offseason. It remains to be seen how heavily involved in either market they’d be, though given their declaration and desire for starting pitching, one would assume they’ll be in the mix to some degree.

But what happens if they fail? They’ve already missed out on Russell Martin, and signs point to them doing the same with Jon Lester as well. What if Scherzer returns to Detroit or ends up in St. Louis? What if Shields ends up in Miami, or perhaps back in Kansas City? There will be any number of teams involved in the sweepstakes for each. Where do the Cubs turn if they fail to acquire the impact starter they covet through free agency, having missed out on the player they sought the most, in Martin?

The Cubs aren’t going to throw money around just for the hell of it to say that they tried and are ready to win a World Series in 2015. However, an offseason without any of the top three starting pitchers and Martin would largely be considered a failure by the majority of the Cubs’ fanbase, as well as those around the game. As a result, the Cubs would likely have to turn their attention to the trade market. Cole Hamels is a player that the front office likes, obviously, not only due to the fact that he’s one of the game’s premier pitchers, but that he was claimed by the Cubs on waivers last season. Jordan Zimmermann is also a possibility, if the Cubs were able to sign him to an extension.

Of course, then there’s the possibility that the Cubs don’t want to part with any of their impact prospects, which would likely be necessary in a deal for either Hamels or Zimmermann. Then you’re looking at an offseason where the club goes after Jason Hammel for their rotation and Jonny Gomes as a bench bat/leadership guy, as well as maybe some catching depth somewhere. Toss in a reliever, if they can find a cheap lefty somewhere. Would that excite anyone and have Cub fans continuing to think those same positive thoughts that accompanied the Joe Maddon hiring.

Obviously this is an organization that is relying heavily on its young talent to carry them into the future. However, the supplemental talent, mainly impact pitching, is crucial to that success (as obvious a statement as that may have been). Leadership is also a necessity for this developing team, even as guys like Anthony Rizzo take on leadership roles as they grow as Major Leaguers. A failure to acquire a frontline starter, even with the availability (or potential availability) of guys like David Price or Zimmermann next offseason would immediately be deemed a failure, and rightly so.

It is still early, though, and once Lester signs in Boston (assuming that there’s truth to all of these whispers), the market for the other two impact pitchers should start to pick up. At that point, we’ll get a clearer picture of where the Cubs stand and what they plan to achieve this winter, the first one in which they’ve actually stated their desire to add to their club, rather than subtract.

About Randy Holt

Spending his days as an English teacher, Randy spends his afternoons, nights, and weekends as a writer on the Bloguin Network, as well as SB Nation. He is a staff writer for both Puck Drunk Love and The Outside corner, as well as Second City Hockey and Beyond the Box Score on SB Nation, showcasing his love for both hockey and baseball, as well as run-on sentences. A Chicago native (and Phoenix resident), he is an avid Game of Thrones viewer/reader and lover of red meat.

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