Image courtesy of

The 2016 World Series was one of the best World Series that I ever saw. Despite the fact that I’m not a fan of either the Chicago Cubs or the Cleveland Indians, watching Chicago win their first championship since 1908, was one of the most memorable moments in my time following this great game. That said, it’s disappointing to see them decline so quickly, their fans deserve better. The Chicago Cubs seemed to prioritize improving their offense, but have so far only added Daniel Descalso. They are also dodging their fans and admitting that they‘re basically skipping this off-season. How can they do that in a competitive division?

What should’ve they done? First of all, I would add $20 million to their budget by not picking up their team option on Cole Hamels. Let’s take a look at his FIP over the last 3 years:

2016: 3.98

2017: 4.62

2018: 4.49

How about his HardHit%?

2014: 26.8%

2015: 27%

2016: 32%

2017: 36%

2018: 41.9%

In short, he’s in decline and despite modest success in 2018 with the Cubs (2.36 ERA and 3.42 FIP in 76.1 IP), he’s a bad investment at $20 million. Steamer projects him to pitch 172 innings in 2019 and finish with a 3.90 ERA and 3.94 FIP.

I would do this trade just like it happened in real life, as Drew Smyly just isn’t worth $7 million. I would also trade Ben Zobrist to Seattle for Edwin Encarnacion and then flip him to Tampa Bay or Houston for any low level prospect that they would give. Seattle would love to save more money and both are only under contract for one more year, with Zobrist being versatile unlike Encarnacion. Tampa Bay has money this offseason and the need and so does Houston. Zobrist is coming off a good season, but at 38 is likely declining soon and $16 million is too much to pay him in 2019. I would sign Brad Brach to the same deal that he received.

Ideally I would trade Tyler Chatwood to the Los Angeles Angels for Zack Cozart or to some team for any minor leaguer to just dump his salary, but that’s unlikely to work. However, I would do a “change of scenery” trade, by trading Jason Heyward to the St. Louis Cardinals for Dexter Fowler. Heyward might benefit from going back to St. Louis and Fowler might benefit by going back to the team that he won the World Series with and was a fan favorite on.

Next, I would trade Jon Lester to Philadelphia in a salary dump move. Wait what?! This move is a bit tricky as he has a no-trade clause, but it’s one that makes sense for both teams. Lester is guaranteed $27.5 million in 2019 and $20 million in 2020. His FIP however declined annually since 2015. Take a look:

2015: 2.92

2016: 3.41

2017: 4.10

2018: 4.39

His ERA’s have remained largely solid however:

2015: 3.34

2016: 2.44

2017: 4.33

2018: 3.32

Would you like to see his Steamer projections for both for 2019?

ERA: 4.35

FIP: 4.30

Is that production worth $27.5 million? What if we could convince Philadelphia (who have money and the need for a stabilizing veteran presence in their rotation), to take him on for basically nothing? We’ll even pay $5 million of his salary, putting him at $22.5 million for 2019. Of course we then have to convince him to waive his no-trade clause, but perhaps a chance at being on a team that’s actively trying to contend, is more appealing than being on one that seemingly peaked in 2016. Let’s assume that he would, maybe because Philadelphia guarantee to pick up his $25 million option for 2021, that we tell him that we won’t.

At this point we have $20 million (Hamels), $16.5 million (Zobrist) $3.5 million (the difference between Heyward’s and Fowler’s contracts) and $22.5 million (Lester) available. This adds up to a whopping $62.5 million. Now what can we do with $62.5 million?

Let’s first assess the team as it currently stands… looking towards the rotation, Kyle Hendricks and Jose Quintana are on affordable contracts and have upside; Yu Darvish is untradeable due to his contract and missed 2018, but has upside as well. We still however have two spots open after losing both Hamels and Lester. How about signing Gio Gonzalez to a 1 year deal for $7 million with a team option for $10 million for 2020? That still leaves us with $55.5 million and gives the Cubs an inning eater, who most likely won’t be much worse than either Lester or Hamels and at a fraction of the cost. What about the other rotation spot? A mid-level prospect should be able to get Sonny Gray from the New York Yankees. We now have $48 million left at our disposal.

Let’s turn our attention to the bullpen: Steve Cishek, Pedro Strop, Carl Edwards Jr., Mike Montgomery (rotation depth), Tyler Chatwood (rotation depth), Brad Brach and Brandon Morrow are a solid collection and I would be on the look-out for bargains but with the volatility of bullpens, I don’t see much value in spending too much on relievers.

Looking towards the lineup, the one area that sticks out is shortstop. I would move Javier Baez back to second base, in order to sign Manny Machado for 10 years and $320 million, leaving us with $23 million.


Let’s add this all up. Keep in mind that their projections are for players on their current teams and that their results would be different playing in new home ballparks. I also doubled Gonzalez’s WAR as Steamer projects only 92 innings for him in 2019, when he hasn’t pitched less than 171 since 2015. I also have higher expectations for Fowler, so raised his projected WAR from 0.9 to 2.0.


Ben Zobrist: 1.5

Jason Heyward: 2.1

Cole Hamels: 2.4

Jon Lester: 2.0

TOTAL: 8.0


Gio Gonzalez: 1.6

Dexter Fowler: 2.0

Sonny Gray: 2.3

Manny Machado: 5.1

TOTAL: 11.0

This is 3 extra wins. Fangraphs predicts St. Louis to win the NL Central with 86 wins and the Cubs to win the second NL WildCard with 85. Those 3 extra wins give Chicago the division and send St. Louis into a tie with the New York Mets for the two NL WildCard spots. There’s also the extra $23 million for the payroll.

What do you think?


  1. Dexter Fowler is owed 49.5 million over the next 3 years. Heyward is owed 106 million over the next 5 years. Why on earth would the cards make that trade? Zero chance.


    • Heyward is better in every way so that’s why. He’s only making a couple more million than Fowler per year now and in the two extra years he’s making $22 million each. Assuming they can fix him it’s not a bad deal.


  2. Without galvanizing one side or the other, main point is the Cubs made a mockery of this offseason after promising that moves they made in 2017/18 wouldn’t affect the ‘19 window.
    This core group is good and in their prime, adding Harper or Machado immediately makes them the team to beat in the NL.
    If $$ was an option, Picking up Hamels deal was pointless with Montgomery and Chatwood available, as well as the starting market going cheaply. If Gio Gonzales is your 5th starter, you’re doing fine.
    There’s 100 more points/counterpoints here, but I’ll end with these:
    The cubs haven’t made any effort to lock down their internal talent with Rizzo-like deals, huge mistake- With the exception of Baez and Bryant, guys like Hendricks, Contreras, Almora, Russell (pre nonsense) would have jumped at 4-6 year deals for 50-60MM. Next problem is Boras is going to come back to the Cubs and demand a 10/350MM deal (or whatever Arenado gets) and instead of having this team, they’ll all be 30+, with probably an entirely different pitching staff. Already hearing Bryant is committed to moving on due to the business moves of the past.
    Fact remains the Ricketts have made a load of cash, are bringing in a huge TV deal, and are acting like a small market team- ticket prices are up nearly 32% since in their 19 year tenure, and yes we won a World Series- but we should expect more and not be avoided and mislead as this author points out.
    Based on this off-season and the comments coming out of the front office, I no longer see the grand design- and I think Harper signs a 8 year deal with an opt out and he and Bryant head west (home) to link up w Trout in ‘20

    Liked by 1 person

    • Exactly that has been my whole point. They claimed that they will fix the offense and then did…nothing. That’s why I said that they should’ve declined the option on Hamels and I’m glad you agree that Gio is a bargain.

      Great point on the pre-arb deals, the Cubs should’ve locked more of their young talent up and the mistakes with Bryant are likely leading to him leaving when he hits free agency in a few years.


  3. In my opinion, your trades water down the strength of the team and do little to add to the weaknesses which are bullpen and situation hitting. To free up money, I would try to unload Heyward by attaching Adolazy, Hoerner and Bote for a bag of balls. Cut Russell, sign Machado move Biaz to second. Outfield roation of Zobrist, Schwarber, Almora and Happ.


  4. Hamels is a gamble, no question but certainly a better option than Chatwood in the rotation. Heyward improved last year with the bat, and defensive runs saved is worth something too. Lester and Zobrist are great veterans, yes they make a lot, but project value. Many said the same thing about signing Ross, calling it a waste of money, roster spot, and making the lineup weaker. Turned out pretty damn well.

    This team is built well for the most part. 2018 saw 95 wins and third in MLB ERA. It’s offense that needs to step up. Adding an ego like Machado would be like having Sosa back. Harper to a lesser extent. What the Cubs need is to have the players they have play to their potential. Bryant at full strength, Russell to remember how to hit, and Happ figuring it out would propel them further than last year.


    • I agree that Hamels is a better option than Chatwood, I just don’t think that either Hamels at $20 million or Chatwood at all should be in the rotation. The Cubs are talking about not having money to do pretty much anything this off-season so why not cut costs?

      Lester is projected to perform as a #4 starter but get paid like one of the best aces in the game. $27.5 million for an ERA over 4 is a very bad investment. Zobrist is also overpaid and projected to regress.

      I do agree on the offense stepping up, but think that Machado’s comments have been overblown. A 26 year old with his ability should be paid.


  5. You wouldn’t be able to trade Heyward for Fowler without eating a bunch of money in the deal, which would defeat the purpose of making the deal in the first place. The Cards aren’t interested in giving up one under-performing veteran for another with a much larger overall contract.


    • Heyward is better than Fowler and it’s a bad contract swap. There’s no reason for the Cubs to eat any money in the deal. St. Louis gets a better player for a couple million more a year.


  6. This seems to think the world exists in a bubble and you can trade anyone for anyone you want. It wasn’t even worth reading as from the start you clearly don’t seem to grasp that the trade of Smyly to the Rangers was essentially the Rangers getting an arm for having to pay a 6 million buyout if Hamels option wasn’t picked up. The Cubs essentially said we’ll take on his contract if you take Smyly, then the Rangers at least got a possible starter for the cost of the buy out. So you don’t want Hamels on the team yet you somehow think the Cubs could still dumped $7 mil on the Rangers with Smyly. Not sure why they would have done that deal being on the hook for Hamels buyout and then pick up an expensive question mark? umm okay.


    • I specifically said that there are no trade clauses but each trade had a valid reason to work.

      1. Lester trade: Lester’s team option is picked up by Philadelphia and Chicago helps pay contract.

      2. Heyward/Fowler trade: change of scenery.

      3. Zobrist/Encarnacion: Zobrist has more value and Seattle save money.

      Your Smyly example is your misunderstanding how the game’s business side works. The Smyly trade wasn’t dependent on the Cubs picking up Hamels’s option at all. There was no provision that the trade could only happen if the Cubs picked up the option on Hamels, so please don’t comment unless you know what you’re talking about thank you.

      I don’t think you understand that the Cubs could’ve still declined the option on Hamels. The fact that they also get Texas to pay for declining it is an added bonus. The S


      • Wow… subtle holier than thou ad hominem attack on me. Suppose I would have expected better of a author/blogger.

        I understand the business side perfectly fine. Obviously there was no provision that the trade could only happen if they picked up the option on Hamels, but there would be no reason for the Rangers to make that trade if Cubs didn’t pick up the option. Why would the Rangers pay for Hamels’ 6 mil buy out and then take on Smyly’s 7 mil salary for a question mark of a pitcher? They wouldn’t. Unless you’re in your fantasy land or give up a lot of prospects, but if you’re going to sell the farm to save money might as well go all out and get rid of Chatwood. However, if the Cubs say we will pick up Hamels’ option if you take Smyly, the Rangers now essentially pay 1 mil more than they had to pay anyways for a possible starter with their weak starting rotation. Makes sense as a 1 mil gamble…. not so much when it’s a 7 mil gamble. As you yourself said Smyly isn’t worth 7 mil.

        I completely understand that the Cubs didn’t have to pick up Hamels. But if they didn’t pick up Hamels, there’s no way that Smyly trade, which you agree with, happens. And that is why your article can’t be taken seriously as you are the one that don’t seem to grasp reality. Somehow you think the Smyly trade happens if the Cubs declined Hamels’ option.

        And because we’re doing ad hominem attacks, please don’t write another post unless you come back to reality. Thank you.


      • I’m only responding in kind. OK, so you agree that there is no provision and that the Cubs could’ve declined the option if they wanted to.

        Maybe the Rangers were interested in a cheap pitcher that they would get for virtually nothing on a one year deal, did you consider that possibility? They didn’t have to acquire Smyly, they could’ve saved their money, but they did. Why? They wanted him.

        Let’s suppose the Rangers wouldn’t have done the trade for Smyly and you’re right, it doesn’t affect any other transaction in my article, so why are we talking about it?

        The fact is the Rangers didn’t have to trade for Smyly, but they did. Would they be less likely to trade for him if they had to pay Hamels’s buy-out? Maybe, or maybe they would still do the trade. Maybe then they don’t do the widely panned Lynn deal or their other questionable moves this off-season.


  7. The only thing I agree with is maybe trading Zobrist. I think Chatwood is untradeable right now. No team is going to take Jayson Heyword unless the Cubs eat a good portion of the salary. That much money for a gold glove right fielder who simply is not a good hitter right now is just not wise. Hamels is a gamble at 20 million, but I think that was the right move. Lester is still a horse, but I don’t think he brings back enough value. I’d deal Happ or maybe Schwarber for prospects, trade, and sign Marwin Gonzalez. The financial reality just doesn’t allow to sign big name relief pitchers. The keys are Morrow, Darvish, Contreras and Bryant. If even three of them can bounce back the Cubs will be just fine.

    Liked by 1 person

    • I agree on Chatwood and am glad that you agree on Zobrist and the relievers. think that a bad trade swap for Heyward is possible if he waives his NTC. I do think that bounce backs are key for them and Marwin would be a good signing.


  8. Your trades r nuts. First, getting rid of Lester makes no sense he is the undeniable leader of the pitching staff and adds value as mentor to the others. He would not go to Philly they already have Arrietta. If Lester just repeats what he did last year that would be more than enough. No one will take Heyward which is why they won‘t bid on Harper, if Heyward played like he did in Atl or St.L then they would see the value in Harper and not so much the risk. Same with Chatwood you can‘t get anything for him. You cannot use him as a reliever he walks too many already have that problem with Edwards. I also would not trade Zobrist, clear veteran leadership, one of their best if not the best clutch hitters they. In fact, if he hits like he did last year, I would then try to extend him a year. This would give Hoerner time to develop, and having Zobrist at 2nd keeps stability in the infield. I would try to trade Russell, maybe somebody’s would take a chance and the Cubs could get back a low level prospect. They really need a solid lefty reliever not just a Loogy, that‘s where they need the most help and you did nothing to address that.


    • The Cubs are penny pinching and Lester is well overpaid. $27.5 million for a guy whose K/9 are now below 7.5 and who is projected for an ERA over 4 in 2019. Why would Philadelphia pass on Lester because of Arrieta? They need a veteran for the rotation and have the money.

      “No one would take Heyward?” Plenty of teams would for their own bad contracts. Zobrist provides veteran leadership but at a price that he isn’t worth anymore. He’s 38 and giving him more money is a major mistake. Trading Russell is pointless now as he barely has any value. I do agree with you on a lefty reliever.


  9. Sure, some of those trades might sound nice, but it takes two to tango. If Heyward could go to St Louis for Fowler it would already be done on the Cubs side. This piece is simply an over-reaction. They explained they have a lot of players they want to see where they are at in the process and many of the “upgrades” are not that gigantic. We enjoyed the cheap years of some of these players, now they are getting expensive. It’s a simple reality and the off-season is still not even over yet.


    • The simple reality is that management put the luxury tax over the team’s needs. That’s the general consensus among industry experts. Obviously Heyward for Fowler needs to be agreed upon by both teams and there’s no trade clauses to consider, then again it’s possible neither side even considered this trade idea. As far seeing where they are in the process? That’s an excuse not to improve the team and the opposite of what they said when the off-season started.


  10. A total waste of time reading this. Are you under age? The difference between Heywards and Fowlers contracts is NOT $3.5 million!! That is an imposible trade! And Sonny Gray is rubbish. Nobody will pay Machado more than $20 mm per. Agree with your take on Hamels and Zobrist, but thats it.

    Liked by 1 person

    • I was talking about the difference in AAV and specifically mentioned it. Gray is a former Cy Young candidate who pitched like an ace outside Yankee Stadium, he is certainly not “rubbish”. Machado isn’t getting more than $20 million per year?! Not only is it completely against all logic but it’s simply not even remotely happening. I’m glad that you agree on the latter however.


  11. Jon Lester wouldnt be dealt before his contract expired in any alternate reality, and Sonny Gray was traded to the Reds and signed a contract extension back on January 21st. Just saying.


    • I know about the Gray trade, this article presumes that the Cubs would beat their offer. Lester could definitely be traded if he waived his no-trade clause and the Cubs find a taker.


      • Why would Lester waive his no-trade clause, though? He’s already on a very good team (quiet offseason or not) that’s already treated him to a World Series ring.


      • He has a team option for 2021 for $25 million. The Cubs can refuse to pick it up while Philadelphia can agree to do it. There’s no chance he’s making that much that year as a free agent.


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s