Morning Cubs Roundup: Offseason schedule and updated arbitration estimates


Offseason Dates

With the World Series set to kick off next week and conclude by the end of the month, now is a good time to refresh out memories regarding some important dates and focal points for the upcoming offseason.

Free Agency: Free Agency will kick off five days after the conclusion of the World Series. This would place it during the first week of November this year. During that five day waiting period agents can begin negotiations with teams, but no signings become official until it is over. Teams must also decide during that five day waiting period whether to extend the $18.9M qualifying offer (the Cubs have no free agents they would even consider this with).

Count on this being a crazy offseason. The top handful of players on the market figure to be the only ones not majorly affected by the pandemic. The best guys will still get top dollar. You can take that to the bank as surely as they will. But where exactly is the cutoff between “The Upper Class” and “The Upper Middle Class?” Because that’s the segment of players who will be squeezed the most.

We’ve recently seen the Cubs become the beneficiaries of presumed high-dollar players not finding the market they initially estimated. Both Yu Darvish and Craig Kimbrel were big name, highly successful pitchers with long track records expected to sign deals above what the Cubs were willing to pay, but due to various factors (durability, declining velo, etc) the markets for both were cooler than anticipated and the Cubs were able to swoop in late and secure both on smaller contracts.

It has happened to a couple of players each of the last few offseasons. Count on it playing out with even more this offseason.

There is a flipside to that scenario which could play out, however. There are going to be players and agents who do not want to be left holding out for top dollar when there are going to be far fewer dollars to go around. Some will attempt to secure short-term (even one year) deals early in the offseason in the hope of riding out the economic downturn in order to re-enter the market once a true recovery takes place.

I know it isn’t an exact parallel, but NHL free agency kicked off last week and we already witnessed the top free agent, a former MVP (Taylor Hall) in his mid-20s, once expected to sign an eight figure deal for at least seven seasons in length, instead settle for a one year, eight million dollar contract.

The equivalent of this in MLB which we could see is a higher percentage of players who receive the qualifying offer simply accepting the $18.9M for one year. But it is for this reason that teams will be even more careful extending the offer to players they either want back or they are 100% sure will not accept. The date has not been determined but a player must decide within about two weeks of receiving the QO whether they will accept it.

I expect many of those middle class players will look to sign early for the best offer they receive. I don’t envision many 3-4 year deals in the $40-75M range. The $100M+ deals will still occur, but those mid-level players seeking mid-level salaries will likely only find that salary offered on a short-term commitment. A few might be able to work out heavily backloaded or deferred contracts though.

Deferred payments will likely play a bigger role this offseason than any other. The huge deals signed by the like of Max Scherzer and other top players have often included some form of deferred payments in recent years, but I wonder if we’ll start seeing it trickle down into smaller deals. For instance, a mid-rotation starter who would normally get a 3-4 year deal at 15M per might end up with a contract which looks the same on its face when reported, but as details leak out we discover the player may only receive 5M or so next season, with the rest of the $10M owed spread out over a five or ten year period.

One outcome I fully expect: there will be far more fringe veterans forced to accept Minor League deals with non-roster invites to Spring Training than is typical. The Cubs found success in this arena with Jason Kipnis and others in 2020, and with more veterans getting squeezed out of guaranteed deals this winter, there will be plenty of guys faced with the choice of an NRI, working out on their own hoping for an injury which opens up a spot on a team during ST, or maybe even just retiring or taking the year off. We could also see more players pursue overseas.

All of this is to say… expect the unexpected. And while some of my guesses above may play out, some others will not.

Owners/GM Meetings: The usually scheduled meetings for mid-November have been cancelled. This has typically been a target time for some UFA deals to be finalized and lots of trade scenarios begin to take shape.

The same dealings will take place, but with no physical meetings, I expect there will be less pressure to get things done and we’ll see news trickle out at a slower pace and instead we may see an even bigger flurry of activity than usual around…

40-Man Roster Deadline: Each team must set their 40-man roster by November 20th for the purposes of the Rule 5 Draft (which takes place in November). There is a always a lot of waiver and low-level trade activity leading up to this deadline, but with money tight, I expect we seen even more this year as teams jockey to secure as much cheap depth as possible.

The biggest name the Cubs had to make room for this year was Brailyn Marquez but they got the jump on that when they added him to the roster on the final day of the season. The two other prospects who are locks to be added in my eye are Christopher Morel and Corey Abbott. I also expect the Cubs will add at least one of their expected right-handed pitching depth at Iowa: Michael Rucker, Dakota Mekkes, Trevor Megill, Keegan Thompson. If they feel P.J. Higgins took enough of a step in 2020 while at the South Bend camp to be the 3rd catcher in 2021, he could also be added.

There isn’t much of a roster crunch for the Cubs this season so I expect the team will be as active as ever making deals and trying to utilize the waiver wire to claim and then pass talent through to the Minors around this time. You can, of course, check out the full list of players eligible for the Rule 5 Draft over at The Cubs Reporter.

Contract Deadline: Team must decide by December 2nd whether to tender 2021 contracts to their arbitration eligible (and non-arbitration eligible) players. The Cubs have 12 arbitration eligible players this offseason, the most I can remember them having in a while. I did some rough estimates for arb figures in an article earlier this week, but it was with the caveat that I really had no idea how to factor the pandemic into the arb process, so I knew my figures would likely turn out to be on the high side. Well, MLBTR put out their initial estimates this week, and it does appear that arbitration raises figure to be low or in some cases, non-existent this year.

Only 4 of the 12 Cubs eligible are projected to earn more than 5 million:

Kris Bryant: $18.6M estimate (No raise, earned 18.6M in 2020)

Javier Baez: $10.0-11.9M estimate (earned $10M in 2020)

Kyle Schwarber: $7.01-9.3M estimate (earned 7.01M in 2020)

Willson Contreras: $5.0-7.4M estimate (earned 4.5M in 2020)


There are still a couple of non-tender candidates for the Cubs, even if their arb figures are below what I initially expected: Albert Almora (1.575M), Colin Rea (1.0-1.6M), Kyle Ryan (1.2-1.5M), Ryan Tepera (1.2-1.5M), Dan Winkler (1.0-1.2M) and Jose Martinez (2.1-2.3M).

Winter Meetings: Scheduled for December 6th-10th, I expect the physical meetings will be cancelled or at least scaled back from previous years, but this will remain a crucial focus point for the offseason. Typically we see the largest UFA deals and many big trades go down during these meetings. The amount of activity could soften this year, but it won’t evaporate, and could potentially increase as teams look to shape their roster to their new budgets.

Rule 5 Draft: On the final day of the Winter Meetings the Rule 5 Draft will be conducted. This event rarely has an impact equivalent to the amount of time and ink devoted to it, but I do expect to see a greater number of players selected this offseason than in recent years. Again, it offers a means to secure cheap young depth, a commodity which should be in high demand. Of course, it could play out the opposite, with teams protecting more of their own talent on their 40-man rosters in fear of losing it. We’ll see.

Arbitration Deadline: In Mid-January arbitration eligible players and teams who have not come to contract agreements already must both submit salary figures to an arbitration panel. Negotiations and agreements can still take place until the actual arbitration hearings which happen in early February.

Teams are typically loathe to go to actual hearings, not just because they may lose (in which case the arbiter chooses the higher salary the player filed) which the team must accept, but the nature of the hearings basically forces the team to argue against their own player which can lead to hard feelings. The two sides typically work out an agreement somewhere in the middle ground before the hearings take place.

With budgets tight though, I expect more teams will take hard line stances and be more willing to fight, regardless of the result (although the some of the players who have the best chances of winning their cases and be awarded salaries teams would deem too high may simply get non-tendered or traded earlier in the offseason).

Filed under: Morning Cubs Roundup


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  • Well done, Michael. The uncertainty surrounding the future financial situation will surely have a big impact on this offseason. Many teams literally won't have much money to spend, and I expect several FO's to get very creative in the trade market. Teams will be hoarding young, inexpensive talent more than ever before yet may be willing to sell low on proven players in order to reduce short-term payroll obligations.

    I agree that many mid-level FA's will settle on short, 1-2 year deals until the financial picture clarifies. I also think good players can be had at a reasonable price through trade by teams with the recourses to take on salary. The Cubs are one of those teams, and I believe this sellers market can work to our advantage if we choose that route.

    The Cubs are in a natural transition period with the impending free-agency of the core offensive players, the expected changes at the top of the FO, and the uncertainty of the financial details of a new CBA in (hopefully) 2022. This year of artificial short-term austerity in the player-movement market could work in our favor.

    I know some fans wouldn't mind seeing a tear-down and rebuild, but I don't see that happening. I don't even see the necessity of a "step back and reload" 2021 season. We have a competitive, yet imperfect, team next season, even if we do trade away a core piece or two. There is no reason to punt away a competitive season, and I don't expect to.

    We have tremendous salary coming off the books after next season and unlike some other teams, we have the future revenues and financial might to take advantage of this sellers market. Whether that be with back-loading contracts and/or deferred salary, as Michael suggests, or simply filling holes and upgrading the roster with the availability of short-term fixes, we can remain competitive while also addressing the longer-term needs to assure ongoing success.

    I'll be disappointed if we don't seize this unique opportunity.

  • In reply to BarleyPop:

    *Buyer's market. I don't fix typos, but that was a mistake and changed the context.

  • In reply to BarleyPop:

    Are the Cubs in a financial position to take advantage of the new 2021 MLB market? Phillies have a 25 year $2.5 Billion dollar local TV deal, plus a percentage of ad revenue? I think a lot of other teams might be in a much better position than the Cubs to spend this season?

    Barleypop, Cubs tried to get under the cap last off-season, & failed because they didn't trade Quintana, or a single core player! You think/hope the Big market Cubs, are going to spend on value deals this off-season? I hope you are right, but Cubs have shown for two off-season status quo is perfectly acceptable, and that was before revenue fell off the cliff.

    I not crying for the owners, but everything the Rickett's own that is tied in with the Cubs, did it all hemorrhaged money? The Cubs baseball team, Wrigley Field, TV network, hotel, Gallagher Plaza, & any other Cub related investments. The Rickett's trying to capture every nickel from Cub's ownership, just hit a bump in the road, and maybe a larger bump when compared to many other teams? Cubs should almost always be spenders. 2020 off-season is a great time to spend, and make trades for contracts? It is a buyers market.

    The four 2021 free agents are a much different class of players, when compared Cubs free agents over the last few seasons. Do the Cubs really have much talent when you subtract those four hitters? In theory if the 4 core free agents play well, those arbitration contracts should be values when compared to the open market, in normal times.

    It might not be popular, but I would try to sign Schwarber to a VALUE driven multi-year extension, maybe with deferred money, and see if he is willing to make a deal. I would trade Happ if you get decent return value, maybe even package him with one of the other core 4 in a trade.

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    In reply to BarleyPop:

    They do need some young pitching talent though. Hopefully they can get it from Tampa. Trade Descalso (maybe a minor league relief pitcher), and see what Bryant could bring. For Bryant you need a starter and a relief pitcher,. Also, take a look at the relievers they had this year and see what can be done with them.

  • There is a great business book penned by Andy Grove, erstwhile CEO of Intel, called Only the Paranoid Survive. In the early 1980s, Intel primarily made its revenue in the DRAM market; microprocessors were a small percentage of its business. In the 1980s, Korean companies started to sell DRAMs at a much cheaper rate than Intel. Grove and his chairman asked themselves: If a new management team were hired (and we'll be fired if we continue with our current business model) what would they do? Answer: they'd get out of the DRAM business and move to microprocessors. Why do we have to wait to be fired, they asked? Why can't we just do it? So they did, literally walking out the front door and back inside. They said it was an exceptionally hard decision for a current management team to make the shift.

    This is a long way of say that the Cubs are a rebuilding team. The current window has closed. Sure, they could try to patch things together next year, but it really won't work. Is Theo brave enough to tear it down and rebuild? Doing so would hopefully make the inevitable rebuild shorter. Or do we have to live through another directionless year and wait for the new management team to come in and do what needs to be done?

  • In reply to cubs09:

    Well, I don't see a 'tear it down', but if Theo doesn't do something of significance, many fans will not be very excited about 2021. No Cub fan is looking forward to watching that inept offense another year. I would not bet that we won't be doing just that though. Sometimes, or should I usually, what one wants to do never materializes.

  • In reply to 44slug:

    My hope is that Ricketts steps in and tells Theo to tear it down and not handcuff the next management team. My guess, however, is that you are right and it won't happen. Instead, they'll make a serious of moves that won't result in a winning effort for next year, and will prove to be bad investments long-term investments. Namely, signing another pricey starting pitcher and locking Baez into a long-term contract.

  • In reply to cubs09:

    Cubs with Theo in the last season of his deal, are not brave enough to tear it down. They couldn't even trade a single core guy last off-season.

    You cannot spend extra money to acquire more/better amateur players without big penalties. Rebuilds are harder, luckily Cubs are a big market team.

    During the Cubs next rebuild/reload, use their big market payroll/spending advantage to maximize the return for the assets they control. They need to still spend money while rebuilding, and use that money to get creative when making deals.

    Cubs need to start selling some players when values are high. Look at other teams bad contracts, and see if you find some players you would risk bouncing back with other assets attached in the deal. With the state of the team, and minor league system Cubs need to shake things up.

  • To me, rebuilds are inevitable, at least if a team is serious about winning a World Series. Teams convince themselves they can avoid it but the delay just makes the inevitable rebuild longer. The Cubs will tear it down. It is just a question of when.

  • In reply to cubs09:

    Of course, the Cubs need to do something drastic! Cubs have not won a playoff game since 2017. Four of the core hitters are free agents after 2021 season. Cubs need a new rebuild/reload strategy?

    One dumb idea I have. Go sign a starter this off-season to a multi-year deal. J. Odorizzi, M. Tanaka, or ?? Add a top 3 starter or better.

    The rebuild part is to then trade Bryant, Rizzo, Baez, Schwarber, Happ, Contreras, and even Kimbrel. A total white flag sell off for the 2021 season. I understand many MLB teams want to sell.
    Maximize return include money, and secondary pieces. Use Cubs big budget to help improve the return.

    Theo leaves and going into 2022 season?
    Cubs could have the best NL central rotation?
    All of the new controllable assets from the fire sale.
    Payroll flexibility
    Lots of available AB for free agents, and younger hitters.
    Move Jedd Hoyer to president. Bring in an outsider to be the GM, and some other fresh thinking executives.

    Building an offense has to be easier than building a rotation from scratch. If 2022 is a mess of a season trade a bunch of guys again.

    Cubs need to be bold this off-season, because waves and waves of talent never came close to happening. Something like this could be best for the Cubs. Remember Cubs have not won a playoff game since 2017.

  • In reply to Naujack:

    I don’t see the infatuation with Jed Hoyer. What has he done, to differentiate himself from Theo. If I’m Ricketts and he intends to rebuild - then I’d clean house FIRST of all, in the F O. I’d begin by trying to get the decision makers from the Tampa Bay F O. Let the new F O, have the ability to build this back up, the way they feel it needs to be done.
    Why in the world would you trade our chips, and then bring in someone to attempt to rebuild from what’s left. You have to give the new people something to work from.

  • In reply to cubbustible:


    I think the new GM from the outside would love to be in that situation?
    Large market with payroll flexibility
    Good rotation
    Bunch of controllable assets, worth more than a couple draft picks around the 80th pick.

    I see your point when Theo leaves. Jason McLeod should also shown the door when his contract ends in 2021.

    What chips will Cubs have to work with a year from now? I have zero issues dealing all seven this season, a total white flag 2021 fire sale. Are you really trading away much control? Four free agents after 2020, Kimbrel option, last year of Contreras, and two years of Happ. currently ranks Cubs as the 26th minor league system.

    We all know Cubs are not paying two front offices in 2021.

    I look at the Cubs if they keep the band together for 2021 with minor addition- could finish anywhere from 1st to 4th in the NL central. Looking beyond 2021 if the Cubs keep things mostly together for 2021, doesn't look pretty to me.

    How hard is it to build a lineup from scratch for a large market team?

  • In reply to Naujack:

    Naujack, you make good points. Especially about the fact that the trade chips are mostly gone, after 2021. That does move up the timeline of when decisions are going to have to be made.
    I guess my bigger concern would be the retention of Hoyer. I done with him. IMO that once Theo moves on, we need a clean break and a very fresh approach - towards type of players drafted, coaching philosophy towards hitting and type of arms they look to acquire.
    I may be wrong, but wasn’t Jed the GM we can thank for giving us Rizzo for Andrew Cashner.
    Anyway, I just wanted to clear up my feelings about keeping Hoyer around. If Theo leaves, Jed should be heading to the airport along with him.

  • In reply to cubbustible:

    I think Jed was with the Cubs when we got Rizzo from SD.

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    So the salaries of Baez, KB, Rizzo and Schwarber come off the books by 2022. The Cubs aren't going to let them all walk, so who do they keep and who is gone? How much money can we shed then? I don't think the Cubs let them all go, some will be extended and the others traded. This is where our drafts and IFA signed is so important. The players I see coming and contributing in 2022 are Marquez, Davis (possibly), Alzolay, possibly Amaya, Jensen, and Morel. That means that everyone except Baez is replaceable and there is a Korean 25 yr old SS named Ha-Seong Kim that is going to be posted and he could step right in and play. He's going to cost a lot and most teams will try and sign him, but with him we would have an at the least above average SS and possibly elite. He could play SS and move Javy to 2nd or I remember how good a 3rd baseman he was.
    I loved the 2015, 16 and 2017 teams but something is out of wack and I just don't see us getting the band back together again. They might reclaim what they had with other teams but if we get talent back I'm willing to do it. Of course, it isn't my money, but something has to be done.

  • Sorry if I missed it but is there an estimate of the luxury tax levels? Would seem the amounts would go down given the lack of revenue increases due to Covid.

  • Bye Dusty !

  • In reply to Oldno7:

    Dusty was old school. His managing philosophy often put him in the race, but no cigar in the modern game. An old 'war horse' who refuses to go quietly to pasture. They will have to rip off his uniform. I love Him! The cheating Stros had nothing coming, but Dusty has my respect.

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