You’ve seen it, Surely, you have.

The dog that is always chasing that car down the driveway. Maybe he’s chasing it down the street. Up the driveway. Whatever, the point is that the dog is chasing this mammoth (by their standards) vehicle, barking like a lunatic and has no intention of ever catching it. Because what fun would that be?

Well, that’s the position Cubs fans are in now. We have been chasing that car championship for over a century now and guess what? We finally caught the thing. The question is, now what do we do with it? That’s a question that we (or the dog) never really asked ourselves. But it’s the reality of the situation now.

There are a few ways to go about it, and I’m guessing there are Cubs fans that fit into each of the different categories that can be brought up. There will be some that are just happy they got to see one before they died and will treat everything from here on out as an added luxury. There will be those that will allow for a few years grace period, only really amping back up if the team falls short of expectations a few times.

And there will be those, and this is the camp that I fall in, that want more. I want two words to go together, two words that should never go together. Just like ‘dog’ and ‘car’ – it’s best to leave those two terms mutually exclusive, right? Well, my two words are ‘Cubs’ and ‘dynasty’ – that’s what I want.

How weird do those words look in the same sentence? Logic would tell us to be happy that we finally got that title and we as fans just should ride the ups and downs from here on out. Well, I’m under 30 so I don’t have as much heartbreaking experience as a lot of Cubs fans but I can tell you this, my fandom isn’t wired that way. I’ve been all about the Cubs since I learned how to talk. And I’m not quite Michael Scott, it was before I turned five.


This World Series run was magical. I’ve been struggling to even put it into words. From the devastation of losing Kyle Schwarber early on, only to watch him come back and be a massive part of the World Series to seeing Jake regress a bit to being just a very good pitcher while Kyle Hendricks progressed to being a very good pitcher, it’s been unbelievable. I could write a book on all the happenings of 2016. But this was a team that loved playing together, had the right mix of young kids and veterans and had (and still has) the best leadership in the game. They’re going to be good for a really long time.

But there will be issues to handle this offseason. Lets get into those and see what five areas, in order of importance, Theo & Company will need to focus on in order to turn this thing into a dynasty. A Chicago Cubs Dynasty.



Dexter Fowler is probably going to move on. And to that, I say good for him. He’ll deserve every penny of his next contract. He’s an above-average fielder that will probably still be at least average by that end of his next contract and he’s an on-base machine with some pop added. In short, he’s a really good baseball player.

But he’s going to cost a lot of money and the Cubs are a handful of years away from having to shell out a lot of money. The issue is, not only do you lose your centerfielder, you lose your leadoff hitter. The leadoff hitter that was so vital to the offense scoring runs. So who takes over?

Defensively, the best option is probably to slide Jason Hayward over to center. He’s still be well above-average there but he won’t be considered the best defensive outfielder in the game anymore, as he is in right. That also opens up the corners for an issue we’ll get to later. As for leading off, I have no idea on that one. My gut tells me that Zobrist would be the guy.

I wouldn’t hate paying big money to bring Fowler back. But the issue will be convincing him to trim a couple years off of likely offers he’ll have elsewhere. Even if the Cubs decide to increase the annual salary, I can’t imagine being a free agent¬†when he’s approaching his mid-30’s sounds good to Fowler. This is his last contract, he’ll want to (and should) get every penny he can.



This won’t be too much of an issue in the regular season, there are still a lot of serviceable arms in the bullpen, but it was pretty obvious that Joe didn’t trust many of them when it counted the most. I’ll say there’s pretty close to a zero percent chance that Chapman is re-signed, as he’s reportedly looking for $100 Million. I initially though that Kenley Jansen would be a nice fit, I think he’ll age better, but it sounds like the Cubs Front Office isn’t too excited about paying him big money either.

Instead, it sounds like they’ll try to find a younger guy that they think can be a lights out closer. As the roster currently sits, I’d imagine that CJ Edwards gets that shot first in April. Guys like Strop and Rondon are solid fallback options but none of those names are really putting fear into opposing hitters at the moment.

I’d love to pay up for Jansen, on a five-year deal I think he would be very, very good for the lifetime of that deal. But if they do decide to sign someone and dip down a bit, Daniel Hudson or Brett Cecil make sense. They could even look at Mark Melancon if he’s willing to take a short-term deal. They’ll also have to look at some LHP options, as Mike Montgomery could end up in the rotation.



Well, this is a good problem to have! It’s still a problem though. Kris Bryant will play 3B, Addison Russell will play SS and Anthony Rizzo will play 1B. That’s every day, obvious. Beyond that though, you’ll have Javy Baez and Ben Zobrist that need to play every day. Zobrist will be 36 by early next season, so you could make the argument that he’ll take more days off and between getting other guys days off and the flexibility between both of them, you can make it work. But if Zobrist ends up leading off, he probably won’t get as many days off as you’d think. There also may not be a place for him in the corners of the outfield, depending on what Theo does with those guys this offseason. If Theo wants to go all in on the next few years, a Baez/Soler type of package for someone like Chris Sale may make sense, especially with someone like Ian Happ waiting in the minors.



Another logjam, another good problem to have. It’s no secret that neither of these guys can field, they are helpless out there just trying to stay out of the way. With Soler, some of that is made up for with his massive arm but still, he can’t even track down balls. As much as I love Soler, and he’s possibly my favorite player on the team, it makes sense to field some calls about him this winter. He still has massive potential, both as an on-base slugger and 40+ home run guy. He would net you a pretty solid starter by himself, adding someone like Baez to the mix probably gets you in the Chris Sale discussions. Soler is also better suited for the AL and DH.

That’s all due to the fact that Kyle Schwarber will not be traded. There is no way, it’s not going to happen. His bat is too valuable. I’d imagine that as long as his knee is alright, he’ll be paired with a pitcher next season and will catch one of every five days. You’ll probably get him a day off against a tough LHP here and there and that will leave a few days a week in the outfield. He’ll need to get better in the field, obviously, but his bat is just too valuable. I’d bet on Soler being moved this winter and Schwarber spending most of his time in LF, regardless of what happens at 2B, RF and CF.



The Cubs declined the $10 Million option they had on Jason Hammel. That money can be better put to use elsewhere. Even if the Cubs don’t swing a deal for a front of the rotation stud pitcher, Mike Montgomery can easily slide into that 5th spot and be just as effective as Hammel would’ve been. Now, it’d be nice to keep Monty in the bullpen and find a viable option for the rotation to join Lester, Arrieta, Hendricks and Lackey but we can’t get too picky.

If they are looking to find that guy in free agency, it probably won’t happen. They will not sign Rich Hill and he’s by far the best starter on the market. If you’re asking yourself what they spend money on this offseason, my gut tells me that don’t spend much but rather trade in some of their (blue) chips for controlled talent. Middle of the road options with big potential I think they would have interest in include Shelby Miller and Sonny Gray. Maybe even a guy like Chris Archer, although he would be quite a bit more expensive in terms of prospects with that contract that comes with him.

This is a problem that will sort itself out as the market starts to take shape. No matter what, they’ll at least go into the season with a very good four-man rotation.


Remember, whatever happens, no one can take away the 2016 World Series. Generations waited to see it, it left grown men and women in tears. But there is more to be had, the Cubs are set up to really flip the script and transform from the Lovable Losers to perennial winners.

It’s time to tear that car to shreds.

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