Best Cubs Moves We’ll All Discuss This Offseason

That sucked. While the loss to the Los Angeles Dodgers seemed decisive, the Chicago Cubs window to win is WIDE open. To get back to the World Series will take some tweaking to the roster. With around $70 million coming off of their books, the MLB luxury tax will be $197 million the Cubs will be expected to be players in the offseason. Whether it is via free agency signings or trades, we’re already beginning to talk about it.

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Arrieta/Fowler Theory

I Have kicked around a theory on how Jake Arrieta can remain a Cub. It isn’t a strong theory, and I give it about a 15% chance of happening, there are a lot of things that need to go right, but it’s a theory.

It all starts when the Cubs present Jake with a Qualifying Offer. He will undoubtedly turn it down (like 95% of players do) and enter free agency. As soon as he rejects this, if he signs elsewhere that team would lose their first-round pick in the MLB Draft. Remember this.

From everything we have heard, Jake is seeking a seven-year deal. This is becoming a normal thing for the top of the rotation arms, and however you look at Jake, he is a top of the rotation arm. There is a chance, however, that no team is willing to go seven years for a pitcher who is entering his age 32 season. There could be more questions about a pitcher who has had to reinvent himself multiple times and isn’t the best version of himself entering free agency.

Don’t get me wrong, Jake will have a LOT of interest, and I’m certain multiple teams will get pretty far in negotiations. What I don’t know is if they will be willing to go more than five years, or at least give the team some serious wiggle room in the later years of the deal. If they are hesitant on signing him to seven years based on the pitcher they think they will have, I don’t see them being willing to lose a draft pick on top of it.

Now getting that extra draft pick might help the Cubs in the long term, but it might also have a Dexter Fowler like effect and we see Jake come back to the Cubs with a more reasonable offer.

If you recall, Dexter was having a rough time in free agency after the 2015 season, and most people pointed to the draft pick attached to him as a reason why. After Spring Training had already started, he was moments away from being a Baltimore Oriole. But at the last minute, Baltimore wanted Dex to pay the team for the draft pick they would lose – highly unorthodox. When that happened, Dex and his agent picked up the phone and rejoined the Cubs.

I don’t think a team will ask Jake to pay them for the draft pick, but I think teams will be reluctant to sign him. If that happens, maybe Jake’s price tag becomes reasonable. Would the Cubs be comfortable signing Jake to a five year deal in the $25 million per season range? Maybe even giving Jake a third-year option to opt out?

Pitching staff

It is expected that John Lackey leaves the team, and as Jon Lester may have let out, plans on retiring. I have already touched on it, but Arrieta will likely leave via free agency as well.

One thought is Mike Montgomery stepping into the rotation full-time. I am good with that, IF they find multiple relievers to round out a struggling bullpen (more on that later). There will still be an opening in the rotation, and Lester, Kyle Hendricks, and Jose Quintana will likely need another top of the rotation arm to make this a top of baseball like rotation. Remember, no team has won a World Series without having a pitching staff ranked lower than 10th best in baseball.

So who is available?

The first guy I point to is Yu Darvish. It isn’t a secret, the Cubs front office LOVES Yu (and they also love Yu Darvish). I love making funny titles with his name. The Cubs were in hot pursuit when Darvish came to America, being very aggressive in the bidding process. The Cubs were calling Texas almost immediately after they traded for Jose Quintana, wanting to talk about Darvish.

If Darvish becomes a free agent, he will likely leave LA since 11 of the 11 pitchers to score nine-figure free-agent plus deals signed with a different team. Based on what I have seen online, he will likely be a $30 million a season, five-year deal type of guy, unless he goes off during the World Series. The Cubs are not crazy about six or seven-year deals for pitchers, which probably came from the scars of the Daisuke Matsuzaka signing when Theo Epstein was in Boston. This might point to Darvish being target number one for the Cubs front office.

But in order to compete for a top end of the rotation guy, the Cubs will likely need to pony up the cash and they will have nearly $80 million to spend. So why not sign Jake? Well, Jake is looking for a similar annual salary, but for more years. There might be some more injury risk with Yu, something Bleacher Report tackled and explained away, but a five-year deal with questionable health is better than a seven-year deal with a severe drop in performance. The biggest reason to look toward Yu over Jake is, Darvish’s arrow is pointing up while Jake’s is stagnating at best.

Another interesting name and the Cubs saw him in the 2016 playoffs, Johnny Cueto.

Cueto signed a six-year deal in 2016 worth $130 million with the San Francisco Giants. However Johnny has an opt-out this season, and with a thin pitching market, he could earn himself a raise.

Now there are mixed messages from Cueto’s camp on this. Early on it was all but guaranteed that Johnny was leaving, but after a season in which Cueto was injured and struggled, he’s talked about staying in San Francisco. If he hits the market, I like him in a Cubs uniform. He would also command a five or six-year deal, with $25 million per season, otherwise, it wouldn’t be worth opting out.

Another name likely to join the free agency market is Masahiro Tanaka. He is likely to opt out of his deal and become a free agent but is a curious case.

Tanaka has given up considerably more runs and home runs this season than last while pitching in 20 fewer innings. Interestingly though, he had 30 more strikeouts than last season and the most of his MLB career. But he has a 1.44 playoff ERA, in four starts (three so far in 2017).

There are a couple of other interesting names that would round out a potential 2018 Cubs rotation. The St Louis Cardinals Lance Lynn perhaps being the biggest of those names. But there is also Jeremy Hellickson, Alex Cobb, Tyler Chatwood, and maybe reunions with Trevor Cahill or Andrew Cashner (Cahill could also return as a reliever).

Relief Pitching

2016 with most of the same guys, this was one of the best bullpens in the game. I mean, hell, Hector Rondon was a very viable closer until the Aroldis Chapman trade. But a lot of their success was smoke and mirrors. In 2016 the pen was 27th in baseball in walks allowed, whereas the 2017 team was 30th. This year’s version got away with the walks through the first half of the season, but after that, they began to get punished for allowing extra baserunners. I 100% believe the regression in the pen and increase in walks is why the Cubs have parted ways with Chris Bosio as pitching coach. Well, that and some of what seemed to be public disagreements between him and Joe Maddon early in the season.

Theo talked about getting back to strike throwing, and not fearing solid contact. This should reduce the free passes Cubs relievers were apt to give out. If this is truly a focus this offseason, here are a slew of guys that should be high on Theo’s shopping list.

Per MLB Trade Rumors

2017 those same guys (sans a couple names of course) started out ok, but it all came crashing down around July and August. But this is the nature with relievers. In almost every single account, they are failed pitchers. They failed as a starter, if they don’t close, they usually fail in high-leverage spots. Their very nature says they’ve can’t be trusted.

So Theo and Co have a ton of work to do when it comes to the pen. Here are a couple ways to help inject something into that unit.

I’d love for the Cubs to make a run at Wade Davis, I just don’t know that they will do it. Wade will want a long-term deal and will market himself between guys like Kenley Jansen, Aroldis Chapman, and Mark Melancon. I don’t know if the Cubs will be willing to pony up the years for a pitcher that gave up the highest walk rate in their career, the highest home run rate since he’s become a reliever, and has seen his ERA rise for the third consecutive season.

If the Cubs look towards free agency for a closer, maybe Greg Holland is a guy that can come in. Holland is interesting since he dominated out of the gate this season, but hit a wall in August. This was likely arm fatigue since he missed the entire 2016 season due to Tommy John surgery. He isn’t likely to reach a deal in the Davis like range due to the injury, but will certainly look to sign a multi-year pack with a team.

A pitcher that would look great on the Northside, and is currently on the Dodgers is Brandon Morrow. He seems to be ready for that next step, featuring a 97.7 MPH and of all potential relief pitching free agents, gave up the fourth fewest walks. Morrow will likely look for more money that anyone would be willing to spend on a “reliever” but it would make some sense if the Cubs are signing him to be a potential closer.

I also think the Cubs could look to reunite with Fernando Rodney or Joe Smith. Rodney has a lot of closing experience and had a renaissance type of season. I think he will need to earn the role, but he wouldn’t have the costs that Davis or Holland or even Morrow would bring.

Tommy Hunter has an electric arm and held a sub-3 ERA in his three most used seasons. In 2017 he had a 2.61 ERA and a career-low WHIP of 0.975. His four-seamer averages 97 MPH, the cutter is 94, he has a sinker of 97 MPH as well. What is interesting is, his curve comes in at 86 MPH and is a mile per hour faster than his slider.

Internally the Cubs have options that can step up also. Justin Wilson is 100x better than he showed but will have a lot to prove to get in the good graces of Joe Maddon. I think Theo will press the issue of getting Wilson in games, but he’s got to produce when he’s given those opportunities. If he can put things together, the Cubs would have three guys (Wilson, Pedro Strop, and Carl Edwards Jr) who throw 96 MPH plus. If they added a Morrow or Hunter, that is one hot pen.


Theo mentioned that he doesn’t prioritize a true leadoff hitter, which probably eliminates a leadoff man from the Cubs offseason wishlist. But, if they do try to add one this is the most challenging piece to fix. As it stands there are no spots for a leadoff man to fill. This means to fix it, they will likely need to deal someone from the roster to do so.

The popular names are; Kyle Schwarber, Albert Almora, Addison Russell, Ian Happ, or Javier Baez. Out of those names, Baez, Happ, and Schwarber make the most sense (from afar), but I can make a case of any of them. I actually feel strongly that one (or more) of those names will not be a Cub in 2018. I would actually be surprised if they don’t deal one of them.

Theo has always been a staunch supporter of Kyle, and he continued that support in his end of year press conference. He, without guaranteeing it, said he wants Kyle Schwarber in the clubhouse. His work ethic, his leadership, his personality are traits Theo stresses in a clubhouse, so I continue to stand by Theo’s word on this and will say he is staying.

Happ and Baez can only be traded if the Cubs are acquiring starting pitching. Either of them is somewhat expendable, and Happ is probably an ideal trade candidate. With the Cubs seemingly married to Schwarber, and Baez being more valued to Joe, I don’t see how Happ is on the 2018 season.

Zobrist Heyward Conundrum

Zobrist fell off fast. He went from a guy you wanted to a guy that you’re counting the days for his contract to end. His defense, which was never ‘good’ fell off a lot. His offense was near non-existent. He will return to husband old role of filling in at multiple positions for the next two seasons.

Heyward, I just have no idea what to do with any longer. He can’t hit, but his glove demands to be in the field daily. You can’t carry a defensive replacement throughout a 162 game season, and his salary limits what the team can logically do with him. The only way the team moves him is if they are bringing in another high priced poor signing, or overpays someone to take him on.

Honestly though, Ben will likely be less noticeable in 2018 whereas Heyward will likely be the everyday right fielder. Theo sounded confident that Heyward will once again find his stroke.

The final verdict is, these two will just be expensive clogs on the Cubs train for the next couple seasons. I could think of worse options to be stuck with though.

Movin on up

To be a consistently successful team, you need guys to come up through the minor leagues and contribute. The team has gotten major contributions from young players each of the past five seasons. To continue this, guys like Rob Zastryzny, Eddie Butler, Justin Grimm, and Victor Caratini need to take a step forward and be positive contributors. Each of them, if they make that jump, have the ability to help save Theo and Jed money and possible trade chips.

It would be huge to have some of these pitchers make that huge leap. I think everyone would be ecstatic to see Grimm be that true Grimm-Reaper that he portrays himself as. He has the pitches to be dominate, it is putting it together from a command sense that could be the difference between 5+ ERA Grimm and sub 3 ERA Grimm. This is the same with Butler, he could be an answer in the rotation or can step into the pen. Z-alphabet is a guy that can be that lefty-lefty reliever. Victor will be a great backup catcher, and with a good deal of experience on the major league roster in 2017, should be a contributor on both sides of the ball.


The Chicago Cubs should be one of four teams favored for championships over the next four years. As Cubs fans, we have never been able to say this. In fact, the only team that is better suited to compete long term than the Cubs is the Dodgers, and I think the 2016 and ’17 NLCS’ will be the start of a playoff rivalry which extends through the 2020’s. We may see a team jump up from time-to-time, like the Brewers or the Diamondbacks, but expect these franchises to battle it out for National League supremacy for years to come.

Theo Epstein has promised this organization “sustained success.” Three consecutive NLCS appearances and a World Series title is what sustained success looks like – and it isn’t over. I can’t, nor Theo can’t promise World Series titles, baseball is just too random, but what once was a losing franchise is one of baseball’s powers. Take pride in knowing, each year, the Cubs will be at the top of the favorite’s lists to win it all.

2 comments on “Best Cubs Moves We’ll All Discuss This Offseason

  1. Pingback: Cubs Most Likely to be Traded - CHICAGO style SPORTS

  2. todd gibson

    and astro will be good for 5 years. don’t trade Hendriks almora,happ,rizzo,bryant. they should deal russel baez,shwarber,heyward,zobrist,lester,rondon. what is likelihood of trading for felix. or signing ohatani. I think signing Addison reed and tommy hunter and tony Watson would help relief. and I feel Holland much better for the money than davis. and alex cobb and lance lynn is a given and easy for cubs to do. also maybe jd Martinez to fix outfield, while Lorenzo cain can be leadoff and mike moustakas would be great utility. do you think this is possible. and can we get bob Melvin or mike maddux to help joe maddon pls emal me back.

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