Chicago Cubs: Boras believes Cubs can do whatever they want this winter

LOS ANGELES, CA - AUGUST 30: Starting pitcher Jake Arrieta #49 of the Chicago Cubsis greeted by agent Scott Boras after pitching a no hitter against the Los Angeles Dodgers at Dodger Stadium on August 30, 2015 in Los Angeles, California. The Cubs won 2-0. (Photo by Stephen Dunn/Getty Images)
LOS ANGELES, CA - AUGUST 30: Starting pitcher Jake Arrieta #49 of the Chicago Cubsis greeted by agent Scott Boras after pitching a no hitter against the Los Angeles Dodgers at Dodger Stadium on August 30, 2015 in Los Angeles, California. The Cubs won 2-0. (Photo by Stephen Dunn/Getty Images) /
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It’s no surprise to see Scott Boras holding court at the GM Meetings. He also feels that the Chicago Cubs “can do whatever they want in this free-agent market and the next one”.

I feel like I can’t help but write about Scott Boras. In 2014, I wrote about how he was criticizing the Chicago Cubs for their spending. Mind you; this was the winter before the 2015 season–the first of the Cubs three consecutive playoff appearances. Once again, with some of the most prominent free agents under his agency, his tone has changed about the Cubs. Well, sort of.

Boras continues to pressure the Cubs about their spending. This time, it’s because he feels they can easily afford to spend the money this year and the next, should they choose. I’ve followed the game long enough to know that the Cubs could spend big and get what they need. But there’s a backside to that type of spending, and we’ve seen it before in the tail end of the Jim Hendry years.

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Boras holds court

But that didn’t stop Boras from holding court at the recent GM meetings:

"“And they have a new TV contract coming up, and they have this amazing group of everyday players who are young and gifted. They have all these choices. … The amount of money that’s rolling in, the revenues annually and in the future, the Cubs can do whatever they choose to do in this free-agent market and the next ones.”"

Nevermind the luxury tax or anything like that. The Cubs just need to spend (on his clients) and keep trying to win while they can. The problem is with that thinking that window will get smaller and smaller because of that. While I can’t dispute that the Cubs have money to spend, I also can’t endorse it, either. The Cubs and Theo Epstein have chosen where to spend big money, and where to pass up on the chance. It’s a relative split to this point.

Some you win, others you don’t

When the Cubs signed Jon Lester, it was a calculated risk by Epstein and Jed Hoyer. The knew his history; they knew what they were getting in Lester. And they also acknowledged that in the final years they’d be paying too much for him.  With Jason Heyward, just two years in and the Cubs have “lost” on that deal to this point. There’s time for Heyward to turn it around, but they paid a lot of money for a Gold Glove player only.

Should the Cubs choose not to go big this winter, I’m okay with that. I’d still like to see them grab a starter (possibly Alex Cobb) and a few bullpen arms as they need a hard reset out there. If they make a run at a leadoff hitter, it’s going to cost them. Either talent or money–but it won’t be cheap.

The Cubs need to have learned that it’s not about making the “big splash,” but getting a quality player that fits what you need. Brian Duensing is one that worked well. He was an afterthought by most but turned out to be one of the most consistent arms out of the pen.

Next: Arrieta to the Cards?

If the Cubs DO something big, it needs to re-signing Wade Davis. If there’s mutual interest between the two, they need to make it happen. Closers are a rare breed, and the next one might come out of nowhere. But Davis is still solid, and the Cubs need one in the worst way.

If you thought the rumor and speculation train was rolling now? Following the GM meetings, it’s only going to get more insane.