The Now and the Near Future

For over a hundred years the next season always held some allure because the current one rarely did. There was only an occasional pennant race to hold our attention, and so there was always Next Year, floating just out of reach. Tempting us to look ahead, to dream about the potential World Series glory to come.

Then Next Year happened.

And now expectations are different. After a season clouded by “World Series Hangover” that left many disappointed despite a third straight NLCS appearance, I think everyone is ready to charge out of the gates later this month when the regular season opens. Spring Training is in full swing. The Minor Leaguers have reported for duty on the backfields. Crowds are packing Sloan Park for a glimpse of the new players assembled heading into the 2018 campaign.

Joe Maddon

Joe Maddon

Just like the fans, Joe Maddon, his coaching staff, and the current roster are focused on the Now. The focus deserves to be on the Now. The Now is really exciting. The Now is another championship contender.

But Next Year, and the season after, still require a bit of attention, even if that Near Future is no longer the main focus. While most, be they fan, player or coach, can happily rejoice and linger in the Now, the front office must split their focus between the Now and the Near Future. So, before we allow ourselves to get too tied up in the momentum of this season let’s take a minute to consider what’s to come.

As I mentioned, and as I’m sure you are all aware, the current roster is… pretty good. Comprised of a veteran pitching staff, an ascending core of offensive weapons and a group hungry to reestablish the defensive supremacy they displayed throughout 2016, this team has a chance to be as special, or more so, than each of the three playoff clubs the Cubs fielded the past three years. And if this mix of players works out in 2018, the decision makers have the option of keeping it intact, or applying only minor tweaks heading into 2019.


The team can easily look to internal replacements such as Victor Caratini behind the plate, and with two lefty relievers still under contract (Mike Montgomery and Brian Duensing) the hole left by Justin Wilson could even be filled by a right hander such as Dillon Maples or Adbert Alzolay. Of course, the Cubs will also have the financial flexibility to reach outside the organization to fill either, or both holes. They can even look towards upgrades at other positions should the opportuni*#%cough%*Bryce Harper*#%cough%* present itself.


Things begin to get a bit more tricky after the 2019 season though as half of the bullpen will enter free agency. This is not the overwhelming setback that it could be under different circumstances, given the organization’s recent focus on developing young pitchers. The front office has been preparing for this eventuality and the team could very well enter the 2020 season in a strong position, with a proven rotation, an entire group of position players in the prime of their careers, and then a talented bunch of young arms such as Oscar De La Cruz, Thomas Hatch and Alex Lange breaking in among a few seasoned veterans in the bullpen. If you believe in the young pitching this organization is developing there is a chance 2020 actually becomes the peak for this team.

“Over the past three or four years, everything we’ve done through the Draft or international signings, we’ve focused our time and energy on pitching,” said Director of Player Development Jaron Madison in a recent interview with “We know we have a roster full of young impact players. We did a deep dive this offseason, looking at everything we do from our throwing program in the Minor Leagues to when to push players to the next level to communicating with the big league staff, just trying to have synergy on the pitching front.

“We’re definitely emphasizing changing the narrative and developing quality pitching.”

And this is upcoming scenario is the reason why. Because things get interesting… really interesting, in fact, as major decisions loom following the 2020 season. If nothing is addressed via trade or contract extensions over the next three seasons, then a year after needing to absorb major bullpen departures the club will also face the prospect of 3/5 of the rotation, as well as the current closer becoming unrestricted free agents. And those issues on the staff will be compounded because half of the projected everyday lineup will be set to enter their final season of arbitration and team control as well.


It really may well all come down to just how successful the Cubs develop the group of young pitchers they have assembled. I believe it is very likely they can easily absorb the bullpen departures, but when it comes to replacing three or four starters (if the club chooses not to exercise the final season of Jon Lester‘s deal) in a single offseason? That is a tall task for even the deepest and most talented farm systems.

Sure, a contract extension for Kyle Hendricks or Jose Quintana would make sense and potentially ease the burden, especially if Lester is still pitching well enough to justify picking up the final year of his deal. That would make the task no different than this past offseason when replacements for Jake Arrieta and John Lackey were needed. The Cubs would likely have the added advantage of being able to fill at least one of those slots with an internal candidate, something they could not count on this year. But the club will have far less money to fill any holes with external options given the escalating arbitration salaries to all their young hitters.

Kris Bryant and Anthony Rizzo

Kris Bryant and Anthony Rizzo

If contract extensions for Kris Bryant, Kyle Schwarber, Addison Russell and Javier Baez have not been worked out, the team will face a difficult choice of whether to entertain trade offers for one or more of them rather than risk losing them to free agency with only draft pick compensation as a return. If the team is in line as a World Series contender they could choose to let them play out their contracts (or at least the first half of the season before reassessing at the trade deadline), but if the team struggles over the next two seasons, the winter of 2019-20 will offer a unique opportunity to retool the club.

This is where the development of  top position player prospect Aramis Ademan becomes paramount. If Ademan, or another middle infield prospect like Zack Short, is ready to inherit the role of either Russell or Baez on the roster than the club will have added flexibility to deal one in order to fill a different hole. The same goes for the Cubs outfield prospects and their potential to replace Schwarber if needed. It is fair to say there is unlikely to be any internal replacement for Kris Bryant.

The Coaching Staff and Front Office

An under-the-radar consideration regarding the stability of the franchise is the future of Joe Maddon. Just how much longer does the 64-year old manager want to continue before he begins considering year-round Winnebago trips? Ranked among the upper echelon of managers for the past decade, Maddon now possesses a World Series ring, and will undoubtedly go down in Chicago sports history as an iconic figure. There can’t be too much remaining on his professional bucket list.

McLeod, Epstein and Hoyer

McLeod, Epstein and Hoyer

The organization has undoubtedly been considering potential long term replacements. Along with holdovers like Brandon Hyde, new additions to the coaching staff this season including Chili Davis, Brian Butterfield, Jim Hickey and Will Venable are all well respected baseball men who have received some buzz in seasons past as future managers. The Cubs have also assembled strong staffs throughout the Minor Leagues with a mix of veterans and young up-and-comers.

The son of a long time big leaguer (Max Venable) and a Princeton grad, Will Venable is maybe the most versatile option for the organization moving forward. Originally hired as a Special Assistant to the President/General Manager in 2017, Venable was inserted as the First Base Coach during the staff shakeup this offseason. He credits not only his father, but his former Padres first base coaches (and current MLB managers) Rick Renteria and Dave Roberts as his main influences. Not a bad group to learn from, all things considered. It is possible the nine-year MLB veteran is being groomed as both a managerial and front office replacement. 

He played under Jed Hoyer as a member of the Padres and then worked along side him last fall. Could he one day be the man to replace him? As much as I would love to believe that the trio of Theo Epstein, Jed Hoyer and Jason McLeod enjoy working together so much that the band can stay together for a long time, at some point Hoyer and McLeod are going to receive offers they can’t refuse to run their own clubs. Unlike Maddon, there are undoubtedly opportunities available to entice them away. Despite the long list of accomplishments early in their careers, this group is still among the younger front offices in baseball.

Even if Venable’s future ends up in the dugout, the Cubs should retain a strong front office even in the face of future departures. Madison, along with assistant GMs Randy Bush, Shiraz Rehman and Scott Harris are all held in high regard as well, and will undoubtedly be strongly considered for promotion.

There are many challenges ahead for the front office, regardless of its makeup. Not only do they need to fit all of the roster pieces together in order to extend the window of contention beyond the next few years, but also another coaching staff turnover, while continuing to juggle the non-baseball initiatives like the Wrigley renovations, the creation of a Cubs television network, and a potentially contentious CBA fight with the MLBPA.

It will be a difficult task, for sure. But it is also a fun one, especially with the club likely to enjoy on field success in the meantime. And if there is one thing this front office has shown consistently throughout their tenure it is they are unafraid of a challenge.


Leave a comment
  • It wasn't long ago we were all wondering if "this" year could possibly be any worse than "last" year. Now, we're discussing the potential "peak" of the current team and if they can repeat as WS champs. We waited a lot of years to get here, wondering if these years would ever arrive! Ain't it fun? I enjoyed your musing, but I'm trying to concentrate on THIS year...

  • In reply to Cliff1969:

    Ha. That is why I did this early in spring training. Wouldn't want to distract people once the season is truly revving up.

  • Even though we have the best under 28 yr players in all of
    baseball we still have to look toward the future. Which players
    are a must to sign to exentions soon. This years draft (5
    picks in the top 120) and the international market are very
    important to our future

  • Even though we have the best under 28 yr players in all of
    baseball we still have to look toward the future. Which players
    are a must to sign to exentions soon. This years draft (5
    picks in the top 120) and the international market are very
    important to our future

  • In reply to emartinezjr:

    NYY and Hou would like a word.

  • Madison Bumgarner becomes a free agent after the 2019 season. Sign him and keep it rolling.

  • Eventually there will be a bad season and a lot of those decisions will become clearer. There is no way they can sign all of that group going to FA after 2020, none. Of course I've never thought there was. The only question is are you proactive about it or reactive in terms of finding deadline deals in a season where the WS is out of reach? I don't look forward to those days but they are inevitable. In the meantimes I think this team has at least one more WS win left in them. Personally I think it's this year. I'm probably more confident about this year than I was going into 2016 simply because I wasn't a Hendricks believer at that point and I thought they could have done better than Lackey. This pitching staff, however, I like. I'm not terribly confident in Jon Lester in the regular season but I think the team can now absorb a subpar regular season from him, and hopefully get him some rest because I still trust him as a playoff pitcher. In some ways I look at him like Verlander (clearly he's never quite been at that level though) in that I don't think he will ever have a great regular season again either but who cares if dogged veterans like he and Lester show up in October?

    I dreaded 2018 for a long time. I was calling for a pitching for this season in 2016 (to much derision from my fellow denizens) because I feared this year and the pitching decisions that would have to be made. Unless I'm wrong though I think Theo and company have gotten it done again. I'm all in the NOW, tomorrow can wait. Are we there yet?

  • In reply to TC154:

    If you don't think Lester will be good in the regular season then I wouldn't get my hopes up for the playoffs.

  • fb_avatar

    I do want to concentrate on this season, but as you said, it's ST so why not look ahead. I feel that we might not have a starting player with the Cubs in 2020 in the system now--I trust this FO to find talent and sign them with the IFA penalty up this July. Also, one name you didn't mention as a successor is David Ross. Catchers make great managers and he certainly had the trust and respect of his peers.
    Go Cubs!!

  • In reply to Jonathan Friedman:

    I think the 4 must signs are Rizzo Bryant Contreras and either Russell or Baez. I think you nailed it. Internal replacement for 2b or SS and 2 starters will keep the ball rolling.

    I say that now but who knows by 2022. So many things could change by then.

  • In reply to Jonathan Friedman:

    Agree about Rossy. The entire environment changes when he's in the area.

  • fb_avatar

    I have to imagine Caratini plays the role of Jeimar Candelario this year. Asset that gets moved for a mid-level piece at the deadline. I could see them re-upping Gimenez if he continues to work well with Darvish.

  • In reply to Mike Moody:

    Definitely possible. Gimenez may have another couple seasons in him, and the Cubs do have Rice as an offensive option and Higgins as a defensive option available in the prospect pipeline behind Caratini. Both can be stashed in the upper levels to provide depth over the next couple of seasons.

    And then you have Miguel Amaya coming up fast behind them. He'll begin 2018 as a 19 year old in the MWL, and is probably 3-4 years away, but I am a big believer in him. He is going to be a really strong defensive catcher, just like the Cubs like in their backup at the position, and there is even some offensive upside to go with it, although that aspect is far less certain and could take more than 3-4 years to take form.

  • In reply to Mike Moody:

    Caratini does seem like an obvious trade chip. Although I watched MLB Network the other day when they had their feature on the best 10 catchers. The Dodgers had two, and the sabermetrics gurus said they think a trend may be for teams to try and keep two elite catchers, since the position is so challenging.

  • fb_avatar

    I think you're off on 2020. Kris Bryant's final arb season should be 2021 (and the rest of them for similar reasons). 2015 didn't count as a full season, then 2016 (1), 2017 (2), 2018 (3), 2019 (4), 2020 (5), 2021 (6).

    Still hope something can be worked out because that guy really needs to play his whole career in Chicago.

  • In reply to Mike Moody:

    They will be ENTERING their final arb year. Maybe I should have made that more clear in the charts. Which means if they want to trade them before they become UFA they need to do it in 2020 offseason.

  • I think Contreras is our hardest to replace person this season. I would not mind Joe catching him only 4 times/week, and giving him some starts in LF or DH to make sure he is fresh in October.

  • In reply to AshevilleCubsFan:

    If Caratini isn't traded, a September call up when the roster expands would help Willson get some days off while giving Caratini some MLB ABs and showcasing him at the same time.

  • I've got a couple of questions. First, when do the Cubs get the new TV deal? And secondly when does the current CBA expire? MLB will be in a manure storm, soon. Some Cubs contracts will end the same time as the current CBA ends. After the way this off season has gone for the free agents, I smell a strike looming. And with the accusations of teams "tanking" or cheap owners not wanting to spend the big bucks on the big names. The owners drink 30 year old Scotch in their suites, while the players get Milwaukee's Best. I hope Arrieta gets a team soon. Good luck!

  • In reply to LRCCubsFan:

    TV deal expires in 2019.
    CBA runs through 2021

  • To me this is really a question of 2022/2023.

    A. Of the current everyday players, who signs a ‘Rizzo-type’ contract
    B. Who warrants a ‘max’ type deal
    C. Is there anything of high value in the system
    D. Who can be traded for any value

    As I tend to trust this FO, I think we take the statement ‘you can’t trust future pitching’ to heart, and figure out how we trade pitching prospects for value.

    Throw that all in a blender and decide what to do in 2021.

  • In reply to Gunga:

    It's fun to talk about, but going 4-5 years out seriously you wait until you have to cross that bridge. Too many things can happen between now and then that will dictate what is done.

    But it's spring, let's play 2022 Cubs GM. KB is the crown jewel of the org. You have to think working out his contract has to be the first domino to fall. What about Rizzo? They have to make a decision about him before moving to anyone else, I would think. He is that important, and frankly, his next contract will be a lot of bucks.

    After decisions/contracts with those two, I think the guy they secretly really, really want to keep on the team is Hendricks. Not only is he a great pitcher, but picking his brain on a daily basis is going to immensely help out a lot of pitchers.

    If there is any pre-emptive work being done before that time with the current roster, my money is on those three guys. Everybody else will be to wait at least a couple more years before doing anything.

  • In reply to HefCA:

    I agree, esp. about Hendricks. I would bet that of the entire staff, he will end up with the best overall career.

  • In reply to Gunga:

    The only thing that is an actual probability is that more than half of the present day roster will be different by 2021 but unlike any other time we have ever seen.....that change is not going to be good.
    It would be far more beneficial to try to lock up this young core as soon as possible rather than dumping everything into someone like Harper. Harper equates to Trout.....and empty trophy cases....

  • Recharging - that ought to quiet Greg Simmons down :)

  • fb_avatar

    It's one data point but bat speed certainly didn't seem to be a problem in the video.

  • Schwarbomb auto-corrected to recharging - go figure.

  • ? lol

  • fb_avatar

    Thought I'd throw this out there for discussion. If Heyward continues to struggle, do you consider making him the world's best paid 4th outfielder and going with a starting OF of Schwarber-Almora-Happ.

  • In reply to Mike Moody:

    Yes. I give him until the trade deadline or so though. Best players play come playoff time.

  • In reply to Mike Moody:

    When was the last time our entire starting OF consisted of our own first round draft choices?

  • fb_avatar
    In reply to DropThePuck:

    I'm fairly certain it hasn't happened in my lifetime.

  • In reply to DropThePuck:

    Add in Bryant and Baez also getting regular playing time,.... and you've got 5 of 8 position players all from 1st Round draft picks.


  • In reply to Mike Moody:

    Mike - that could be how it plays out - especially if Happ, Almora and Schwarber are all hitting the ball with authority, they all stay healthy, AND their defense (especially Schwarber's) remains on the upswing.

  • fb_avatar

    Speaking of the present, it looks like Albert A hit another HR tonight. If he and Happ split playing time we could have 25-30 HRs from that position. Not bad, and get a GG outfielder in AA and Happ looks better than I thought he would. This could be a position of power and defense.

  • In reply to Jonathan Friedman:

    Almora is not a gold glove outfielder. He is good but he is not great. There are too many center fielders with insane range right now that Almora simply doesn't possess.

  • fb_avatar
    In reply to Michael Ernst:

    Michael, I respect your opinion but from what I’ve seen he gets a very quick first step and his route to the ball is true. We’ll find out if he plays a lot. I would like to see him start in CF.
    As Mike Moody said, it’s very possible that JHey could be replaced by Happ or that we’d have an outfield of Scwarbs Almora and Happ.

  • In reply to Jonathan Friedman:

    Why would you combine them to hit 25-30 when Happ will get 30 alone and Almora at least 20? Key play here is to swallow some pride and make Heyward the highest paid 4th outfielder in all of baseball. Put him in RF to start the 8th, put Happ or Almora in CF and the other one in LF after at least 3 AB for Schwarber.

  • fb_avatar
    In reply to veteran:

    I think he was combining them as in "25-30 HR out of them as CF" (and allows Happ to hit additional HR as a 2B, LF, etc.). I think if Happ/Almora split time at CF 25-30 HR is pretty reasonable out of CF.

  • Happ is gonna play, somewhere. Out of the six players in contention for five positions, I only see Schwarbs with as much to offer as Happ and his switch hitting bat. A year and a half ago I referred to him as potentially a poor mans Pete Rose and our likely leadoff hitter in 2018.
    LH bats are needed in this group unless JHey is transformed.

  • fb_avatar

    Big Day for the Cubs offense.

    The schwarbenator got a hold of one. Happ continues to make things happen. Court and Freeman continue to rake.

    Quintana was solid even thought the ump was squeezing the heck out of him ( minus the meatball for the Alonso Bomb)

    Side note. Billy Mckinney hits his 4th dinger. This could be the breakout yrs we all been anticipating for him 3-4 yrs ago. I still a little upset they just threw him when I feel ( I have no evidence ) that they could have made the trade w out him. ( Sort of like how a lot of people think Ryan Pace didn't have to move up 1 spot to draft Mitch Trubiskey)

  • In reply to Jim Odirakallumkal:

    Sorry, but nobody gets "just thrown in" I am sure yankees saw the same things we saw in mckinney.

    But so far, none of these prospects we traded that helped us win the world series has had any success at the major league level. In fact no cubs prospect that Theo has traded have had a major impact in the mlb.

  • In reply to bleachercreature:

    DJ LeMahieu and Zach Godley seem to think they have made an impact at the MLB level.

  • fb_avatar
    In reply to CubFanStuckInStl:

    Shhhh......dont tell them that.

  • fb_avatar
    In reply to CubFanStuckInStl:

    LaMahieu was traded for guys that, at most, helped the Cubs be bad and cash in those chips for draft picks. But lots of guys could lay claim to that distinction.

    You have a point with Godley.

  • In reply to Joel Mayer:

    Agree to an extent on DJ but I do believe the FO was hoping that Ian Stewart I believe he was only 26 at the time of the trade could maybe with one more year removed from a wrist injury could regain his power stroke and be a fixture at 3rd base for a few years. He was also regarded as an above average defensive 3rd baseman.Just did not work out but at the time it seemed to be a small price to pay for a worthwhile gamble.

  • In reply to CubFanStuckInStl:

    Yep - that trade seemed like it was fair at the time - and for the reasons that you list CubFan. At the time - Stewart seemed a good bet. Didn't work out that way.

  • In reply to CubFanStuckInStl:

    Ok you got me. Your right on lemahiue. I missed that one. Most definitely a top player.

    Godley has been decent but nothing more.

  • fb_avatar
    In reply to Jim Odirakallumkal:

    The irony is that package wasn't good enough to get Andrew Miller. Now Torres has lapped Clint Frazier, though Sheffield still looks very good relative to McKinney.

  • fb_avatar
    In reply to Mike Moody:

    I still say the Yankees mis-read the market and it actually worked out well for them. I think that what the Cubs offered for Miller was better than what the Indians gave them. But the Yankees thought they could get more. The Cubs moved on and gave up a pretty package for Chapman (better than what the Indians gave for Miller). Then the Yankees were able to go to the well again and found a suitor for Miller. I don't know that the Indians would have given what they gave to get Miller if it meant that they would get Chapman instead. So the Yankees mis-read the market and it actually worked out better for them.

  • Bryant (& Russell, nor any of our guys) is not an automatic lock to extend that some may think... Boras’s clients like to test FA to get the most $$ they can. They’ll need to plan as if they can’t extend any of them, & if they do, gravy. Samardzija gave them their first taste of being rebuffed & then Jake... Cubs have shown they can move on whether it’s by a trade or not meeting their FA $ demands. This day & age players/agents follow the $ & FOs move on from long term &/or high $ deals. Rizzo type contracts are more the exception than the norm.

    That said, of course I want to keep them all in Cubs hats, but we could lose more than 1 of those guys.

  • In reply to Milk Stout:

    This is why I am so intriqued by the current Jake, Moustakas, and Holland Free Agent "negotiations" . And before them, Rafael Soriano and Stephen Drew. And secretly hoping that Scott Boras falls flat on his face as he waits past opening day for some team to meet his client's perceived value. (I DO realize Boras works for his clients)

    And hoping that Kris Bryant, Albert Almora, and Addison Russell find another agent before their walk years.

  • fb_avatar
    In reply to DropThePuck:

    I have said it before, but I think if I am Jake, in particular, I am FURIOUS with Scott Boras. Yes, Boras does work for his clients but I would guess he sold them on "Just wait it out. Don't worry, someone will pony up 6/$180M" or something like that. What I think is most likely now for all three of them is simply sign a 1-2 year "make-good" contract and hope they are effective and don't get hurt. I think the odds of them going into the season without a team is <5% (SOMEONE will sign them). At the same time, the odds of them signing for more than about $20M AAV is equally unlikely with the possible exception of Jake, but even he won't make much more than that. Most teams have their budgets worked out for the year now that March has arrived and most teams won't be able to come up with $25M. Or, if they can, they are bad teams that may not appeal to these FA.

    This has been a weird off-season.

  • As an aside, Boras is now 65, and is reported to have made $11+million last year. How much longer does he choose to remain a factor?

  • In reply to wthomson:

    HIs job is not physically demanding. I don't see him retiring any time soon, unless a number of his clients are unhappy with him and change agents.

  • Great piece Michael.
    It would be really nice if the Cubs don't have to make a big splash at the trade deadline this year.
    I'm also really interested in what the Cubs do in the international market this summer. IFA signings could be key in how the Cubs are able to refill position players while drafting pitchers in the late first round.
    As you say Michael, it should be fun to watch.

  • In reply to couch:

    Given the recent postseason trend to pull starters at the first whiff of trouble and abuse the bullpen, I still expect the Cubs (and every other serious contender) to pick up a rental reliever near the deadline.

  • In reply to DropThePuck:

    We might just bring up Maples or Smily or Alzolay or whoever.

  • In reply to couch:

    The Cubs top 3 pitching prospects are also IFA signings. It’s not just for position players, but I get what you’re saying.

  • Thanks for the article! It's interesting to think about how much of the future plans depends on the homegrown pitching talent to develop. Obviously it hasn't happened yet with this FO, even when attacking the problem with volume and high-ish picks, but the key time will be the near future, as discussed in the article. If that doesn't happen, the FO will figure out some kind of Plan B, but that would likely involve trading assets they were hoping to keep.

  • "Aces gets 7 years" lol. God riddance jake arrieta. Take your overrated declining self to philly and enjoy playing for the 2nd wild card fire boras as soon as the ink dries.

  • In reply to bolla:

    and thanks for the pick!

Leave a comment