Next Monday, December 7th, marks the beginning of Jed Hoyer and Theo Epstein’s newest mission.

Code Name: MLB Winter Meetings.

And it may just hold the key to the success of the Chicago Cubs in 2015 (and beyond).

Will there be challenges along the way? Yes. Will it be all fun and games? No. Will someone go home crying? Probably. But one thing is for sure, pitching will be the main topic.

As it stands the Cubs only have two ‘locks’ to slot into their 2015 rotation: Jake Arrieta and Kyle Hendricks. This ultimately leaves them with some big holes to fill before the start of the season.

Sure the likes of Tsuyoshi Wada, Travis Wood, Jacob Turner, Dan Straily, and Felix Doubront could all fill a spot in some shape or form, but let’s be real for a moment.

Do you really trust any of these guys?

I can get behind Wada getting a shot because he put up a strong 2014 showing. However, Travis Wood was straight up garbage. Jacob Turner showed potential, but still has a lot of work to do. Straily lost velocity as a result of a mechanical change, and well, Doubront was an absolute mess.

Now, I get it, there’s no way the Cubs fill their rotation with three substantial free agent signings, or even two or three trades during the meetings. Which means one or two of these guys is in fact going to get that shot. If I had to pick, Wada and Turner would be my first choices to get an opportunity.

But this still leaves the Cubs with a spot or two to fill.

Anyone with access to the internet knows that lefty Jon Lester is No. 1 on the radar. He’s also my No. 1 choice, and I think the Cubs should be out there coaxing him with fried chicken, beer, and a shit load of money.

So much money that Lester doesn’t need the Cubs to get him fried chicken and beer because he can just buy the establishments that make the fried chicken and beer. As long as it doesn’t inhibit his ability to throw a baseball, of course.

All joking aside, I really do prefer Jon Lester over Max Scherzer. That’s not to say I don’t think Scherzer is a great pitcher because he is; but he’s not worth the type of money he’s seeking.

Last year, Lester split time between the Boston Red Sox and the Oakland Athletics and was effective in both places. He tossed 219.2 innings (a new career high), struck out 24.9 percent of the batters he faced, and walked a career low 5.4 percent. To round it off he posted a dazzling ERA of 2.46 and a FIP of 2.80.

All in all, 2014 was a very good season for Jon Lester.

All that said, Lester isn’t an ace and I know that many feel the same way. But he’s certainly someone you can put at the top of your rotation, and he’s been pretty dependable too- only missing the 200 innings pitched mark once since 2008. 

Another reason I’m fine with giving him quite a bit of money over someone like Scherzer is that left-handed pitchers tend to last longer even if they start losing their velocity.

So what happens if the fun runs out and Lester signs somewhere else?

Well, that’s when the Cubs must start overcoming challenges. In this case, the word ‘challenges’ stands for Philadelphia Phillies GM, Ruben Amaro.

Amaro is notorious for holding his players to the highest value, which just sucks for everyone else. First, his team is old and decrepit as he tends to hoard former stars. Therein lies the problem, because he thinks his former stars are worth star-level returns, when they’re simply not.

So, to work with Amaro, you have to be willing to fold before he gets a deal he likes, because if he gets a deal he likes, you’re likely paying out the ass, and that’s no bueno.

Amaro has someone that the Cubs like, and they might just like him enough to throw Amaro a bone. And that’s another lefty hurler, Cole Hamels.

When Hamels was placed on waivers this past summer, the Cubs put in a claim on him but were never able to strike a deal. Likely because somebody was a bit ridiculous with their asking price.

According to a CSN report out of Philadelphia, the Phillies are looking for at least three top prospects, two of which are MLB ready.

That’s a steep price for the 30-year-old lefty, but he’s on a relatively friendly deal at four-years, $90 million.  His past performances certainly garner that type of money. Last season, Hamels amassed 204.2 innings pitched, a 23.9 strikeout percentage, and a 7.1 walk rate- leaving him with an excellent 2.46 ERA and a FIP of 3.07.

Not too shabby.

However, for the Cubs to play with Amaro, they’re going to have to get creative with their offer, assuming Addison Russell, Kris Bryant, and Jorge Soler are off limits, and I’d hope they’d be.


There are other options out there for the Cubs, but none are as exciting as landing Jon Lester or trading for Cole Hamels. One will cost money to sign and the other will cost prospects, but both are excellent lefty pitchers- a huge need on the North side.

Nevertheless, if the Cubs come away with nothing at this years MLB Winter Meetings, there will be a whole lot of crying, and fans will probably become irrational and start saying the Cubs will never sign anyone.

That’s fine by me though, because Cubs fans can be about as bi-polar as this city’s weather.

If they walk away with nothing, I’ll just say, “wait till next year.”

(Featured Image courtesy of Keith Allison)