The Cubs just finished up a big, big season.

It’s safe to say they exceeded most, if not all, expectations. However, they showed their youth and inexperience in the NLCS and paid for it, getting swept by the Mets.

That’s the bad news. The good news is that this team has as many resources as any team in MLB yet only sits around the middle of the pack in payroll. After tasting contention and knowing they have a nice window here considering they don’t have to re-sign their young studs for a handful of years, they can afford to spend some big money.

Who would fit best? That’s a loaded question, although a few guys really jump out as obvious fits.

On that note, keep in mind that we are only discussing the upcoming Free Agency class and that Theo will probably swing a trade or two as well.


First, lets go over a few things for each group.



What do they do with Dexter Fowler? He’s a good player and only 29, it’s also a fact that they were much tougher to beat when he was able to reach base consistently.

But there are a couple options that, if they can play CF, would be a significant upgrade and constant defensive presence in the OF.

As for the corners, we know Jorge Soler will man RF but what about LF? Does Schwarber stay out there? He clearly has to play pretty much everyday now. If he catches, does Bryant move out there?

The way Theo goes about Free Agency will tell us what they’re thinking.


There are too many young studs already, so they don’t need a ton of help here.

Addison Russell will be your everyday starting SS & Anthony Rizzo will be your 1B, with Javier Baez and Starlin Castro battling it out for 2B. Kris Bryant will obviously be the man at 3B if they choose to keep him there but could he end up in LF?

Maybe Theo tries to move Castro or even (it would take a haul) Baez this offseason, which would clarify things a bit. Bottom line, this is a good problem to have.


This is the biggest concern of the season.

Simply put, the Cubs can’t go into next season with Hendricks/Hammel/Wada as their 3-4-5. We know they won’t, which means they need to address the situation this offseason.

I expect they’ll sign a top-tier guy for big money. I’d also expect they up the per year money a bit and shorten the length of the contract, giving them more flexibility to sign the current young studs when their time comes.

They’ll also need to sign at least one rotation filler, and obviously, the more talented the better. We’ll get into these guys quite a bit.


Theo will obviously look to fill a couple holes and probably get younger. This FO seems to love taking former mega-talented guys that have been cast aside and rebuilding them, we have a couple really solid options that fit that mold.


Lets get to the options that Theo & Co will have this winter.



Jason Heyward (26) – As far as position players go, Heyward would be the biggest prize. While he’s best known for being arguably the best corner OF in the game, he’s still better than 95% of the CF defensively and he does pretty much everything well offensively. He never turned into the 40/40 offensive monster that everyone thought he would but he’s a really, really good baseball player. While the Cardinals won’t overpay to keep him, Theo & The Ricketts will still have to open the checkbook really wide to land him. He’d look really nice roaming CF at Wrigley.

Yoenis Cespedes (30) – Cespedes gets the nod as the next option due to the fact that he can play CF. How long can he play CF? That makes it a bit more murky, plus the fact that he’s much better suited to be in a corner. But that bat would look make an already dangerous lineup downright scary. He’s not as good of an all-around player as Heyward but there is no doubt he has a bigger bat.

Justin Upton (28) – I love Justin Upton and think he would put up stupid numbers at Wrigley Field. There is a big problem though, and it’s that he couldn’t play CF if his life depended on it. Therefore, I don’t see how they could make it work. Bryant in CF doesn’t even solve the issue, Soler or Schwarber would have to move there, or Schwarber would have to stick as a full-time catcher. Lots of ifs.

Denard Span (31) – We’re back talking about guys that can play CF. Span, while being a little bit older and less dependable (as far as health goes) than these other guys, he’s just as athletic, if not more so. He’d step right in and provide solid defense to CF while batting leadoff. He may not go on the hot stretches that Fowler does but he’ll consistently get on base and add a bit of pop.

Alex Gordon (31) – Like Upton, he’d have to play a corner and he has a team option. He would be an option for the FO but a lot of pieces would have to fall in place.

Will Venable (32) – If Theo & Co think Venable could stick as a CF, he’d be a real option. He’d be another LH bat and could possibly hit lead-off. Worst case, you try to get him at a team friendly cost and he’s a plus 4OF. I doubt the Cubs will be re-signing Austin Jackson.


Matt Wieters (29) – Assuming David Ross retires and they keep Kyle Schwarber either in the OF or in an hybrid role, they’ll need to bring in another C. Wieters will give you some pop and can hit from either side of the plate. Also, he’s only 29 and probably won’t demand a huge deal.

Ben Zobrist (34) – Zobrist is a big Maddon guy and Maddon is a big Zobrist guy. He’d probably come on a lower deal and it would only be for a year or two. But he’s versatile enough to play pretty much anywhere, something Maddon loves, and can really hit. The Cubs could stay away if they like Chris Coghlan in this role.

Ian Desmond (30) – The only reason he’s on here is because he’s a high upside, potential power bat. This FO group and Maddon love guys like that, so maybe they’ll give him a shot. But again, with this crowded of an IF, it would probably take a move or two sending guys out for the need to be there.


David Price (30) – Price will be the jewel of this offseason and most around baseball view the Cubs as the favorite to land him. While I wouldn’t hate landing Price, I’d hope they would be able to convince him to take a higher annual number or shorten up his desired contract by a year or two. Either way, Theo & Co will push hard to land him. The Postseason would go much better if your 1-2-3 is Arrieta/Price/Lester rather than Arrieta/Lester/Hendricks, especially (in the postseason) with a Best Of 5/7 series.

Johnny Cueto (29) – Cueto is the 2nd of the Big 3 Arms, and is a few months younger than Price. Personally, I think Price will age better but if they prefer Cueto for any reason, I’d be on board.

Jordan Zimmerman (29) – Everything is similar to Cueto, expect that I’d much rather have Cueto. Zimmerman is almost a full year younger than Price and a few months younger than Cueto. But in my opinion, the other two are just better pitchers and I’d rather pay them their expected asking prices instead of what we’ll see from Zimmerman. But at the end of the day, landing any of the Big 3 would be huge and honestly, pretty necessary.

Marco Estrada (32) – He’d need to come on a few year deal, at most. But you’d be hard pressed to find a more reliable innings eater for the middle of your rotation. Theo will at least inquire to check on the price tag.

Mike Leake (27) – If you ask scouts, they’ll tell you Leake has a ton of raw talent and a ton of potential. I’d trust this staff to get the most out of him and he could start out as a backend guy that could eventually work his way up to a solid or very good #3 arm. I’d be alright with spreading out his money a bit, given his young age.

Scott Kazmir (31) – If he came on a 2 or 3 year deal, I’d love it. Add another LHP to the middle/back of the rotation and let him do his thing. He’ll eat up innings and will very rarely get blown up.

Ian Kennedy (30) – Call me crazy but I think this staff could do really good things with Ian Kennedy. His teammate from last year, Tyson Ross, will be a popular trade target rumor, but Kennedy would be a fantastic option on the backend of the rotation and could even put up big numbers. The only thing that scares me is that he tended to go into slumps of getting knocked around while pitching in a very pitcher-friendly park.

Doug Fister (31) – I don’t think his price would end up where Theo would like but he would be a beautiful 4/5 option in the rotation. Maybe they can convince him with a high per year on a short-term deal.

Jeff Samardzija (30) – Do we want him back? I’d say, if the price is (very) right, sure. You can do worse with a #5 SP, maybe even #4. If all else fails, he’d be a potentially elite bullpen option.


Joakim Soria (31)  – The Cubs Bullpen is pretty solid with ‘Firemen’ type relievers, but they could find a spot for Soria. My guess is that he’ll be a big rich for them but a Grimm/Soria/Strop/Rondon backend would look pretty good.

Antonio Bastardo (30) – That being said, they’ll need another LHP out of the pen. Travis Wood has performed well but really has a niche role while I can’t see Clayton Richard returning. Bastardo can miss bats and would fit in well with this group.

Tyler Clippard (30) – His stock was much higher a year or two ago, so they may be able to get him on the (relative) cheap. Like Soria, he would fit in well and give them another big arm on the backend.

Brian Matusz (28) – Similiar to Bastardo, he would fill the need for a LHP out of the pen. High upside, can miss bats, etc.

Tim Lincecum (31) – Now we get to have some fun. The Maddon/Epstein/Bosio Rebuild Projects! We all know about his past, but Lincecum could be a really intriguing bullpen option. He’s another guy with a big arm that could, even if he hasn’t recently, missed bats. The best part, he’ll probably come cheap.

Neftali Feliz (27) – Rebuild Project #2. Doesn’t it seem like just yesterday that he was the next big thing? We even remember him as a RH Chapman-lite. He’s a BIG arm and he’ll have no problem missing bats if he gets fixed and stays healthy.


Priority 1: Sign ‘Big 3’ (Price/Cueto/Zimmerman) Starter

Priority 2: Sign High-Upside Backend Starter

Priority 3: Finalize Outfield

Hopefully Christmas comes a couple weeks early this season, with Theo locking a couple guys in during the Winter Meetings in Nashville.

No matter what Theo & Co decide on, I have 100% faith in them. You can expect to see the Cubs playing deep into October for a long, long time.

share on: