Jorge Soler became just the second player in MLB history to win a World Series with the Cubs and also hit a leadoff homer in a World Series game, plus he’s the first product of the Cubs system to win World Series MVP. Wild stuff, I know. Soler and the Atlanta Braves were one game under .500 at the deadline, just a half-game better than the Cubs, but they showed everyone their asses and elbows down the stretch to rebound and win it all.
Now, however, all 30 teams are back to a tie and they’ve all got a lot of work to do before pitchers and catchers start reporting in mid-February. The Cubs have not officially set that date yet, but we can be confident in saying Jed Hoyer has less than 105 days to spend intelligently in the hopes of putting together a competent roster that makes good on his claim that this won’t be a long rebuild.
There are more than a few complicating factors in the way — baseball budget, balancing development with free agency, potential work stoppage — and we’ll cover all of them in greater depth as the offseason rolls on. For now, though, we’re going to take a look at all the pertinent dates and deadlines dictating the action over the next few months.
November 3 — Teams and players have five days to exercise or decline options or opt-outs for next season. Players who have reached free agency can only work out deals with their current club during this period. We should hear soon that Nick Castellanos has opted out of his deal with the Reds, after which he almost certainly won’t be working out an extension.
Another interesting situation to monitor is Craig Kimbrel‘s status on the South Side. The experiment of using him as a setup man for Liam Hendriks flopped and the White Sox probably don’t want to try it again, but the prevailing thought is that they’ll pick up his $16 million option and try to trade him.
The Cubs don’t have much to do here because they don’t hold any club options, nor do any of their current players have options of their own. It’s possible they could work something out with Matt Duffy, but Zach Davies isn’t likely to be chatted up for a new deal.
The real action will take place on the 40-man roster because 60-day IL designations expire and eight players must be reinstated. That gives the Cubs 43 players on the roster and necessitates the clearing of at least three spots, with several more required to make room for free agents and to protect prospects from the Rule 5 Draft (more on that below).
November 7 (5 pm ET) — This is the deadline for teams to issue qualifying offers, which dropped by $500K this year to $18.4 million, to eligible free agents. Castellanos will almost certainly be given a QO once he opts out, making him one of what figures to be a record number of offers. The uncertainty of labor negotiations and the increasing value of compensatory picks creates a perfect storm this winter, one that will impact the Cubs’ moves.
Though they avoided any luxury tax penalties in 2021, the Cubs would still have to forfeit their second pick in next summer’s draft and $500K in international bonus pool money if they sign a player who declined a QO. They’d lose their third-highest remaining pick if they sign two such players, so the free agent market will be a minefield of sorts.
Castellanos might be worth the risk and players like Corey Seager and Carlos Correa certainly would be, but that’s still a tough call for a team that wants to do a better job of building from within. The Cubs have reportedly checked in on the elite shortstop market and 670 The Score’s Bruce Levine went on Marquee to say the club should prioritize Seager, so a big splash isn’t out of the question.
Even if that last tidbit may feel like little more than conjecture or opinion, it’s at least mildly intriguing that an employee of the Cubs’ flagship radio station is talking on the team-owned TV network about spending big on a prime free agent.
November 8 — Free agency officially opens, though whether anything actually gets done quickly is up in the air. The last few offseasons have been incredibly sluggish in the early going and have even stretched well into spring training as top-tier players draw out their negotiations. Whether the pending CBA expiration hastens that process or halts it entirely is something we’ll find out soon enough.
November 8-11 — The GM meetings take place in Carlsbad, CA and will likely yield nothing more than a few soundbites from Hoyer and Carter Hawkins.
November 17 — This is when we will start to get a better feel for the market because it’s the deadline for players to accept or decline the qualifying offers that were extended 10-15 days prior. Even if they don’t like the idea of taking a one-year deal, a lot of QO players might accept what will be a much higher annual salary than they’d be able to get on the open market.
It worked out really well for Marcus Stroman and Kevin Gausman this past season, so a potential record number of offers could also mean more acceptances than ever.
November 19 — The Cubs don’t have a lot riding on any of the previous dates, but this one could be very interesting because it’s the deadline for teams to protect Rule 5-eligible players by placing them on the 40-man roster. With about 60 such prospects in the system and a limited number of spots available, particularly if they want to leave room for free agents, the farm could be ripe for the picking.
Nelson Velazquez is pretty much a lock to get a 40-man spot at this point, then there are a number of pitchers that could be added. Rather than simply deciding which players they can’t afford to lose, the front office needs to think about who other teams will most covet. That sounds like two sides of the same coin, but one is about keeping a player and the other is about not losing them for insufficient value.
December 1 (11:59pm ET) — This is when the current collective bargaining agreement will expire, at which point a work stoppage is likely. If the league and union have not agreed to a new deal by this time, and nothing outside of some artificially optimistic statements from both sides indicate they will, owners will likely institute a lockout. That means no transactions until a new deal is reached.
If that happens, the rest of this calendar can be thrown out the window because we’re probably not going to see things resolved quickly. Among the sticking points are the QO and service-time systems, salary floors and caps, and the disparate trends of overall league revenues and players’ percent of the pie. After the tenuous negotiations over the start of the 2020 season, there’s no reason to believe this gets done quickly.
Also, the players hosed themselves by allowing their union leadership to settle for additional creature comforts in exchange for ceding even more financial control to owners. The players are going to want some of that control back and the owners are loath to give it up, so they could be at loggerheads for a long time. Here’s to hoping I’m wrong.
December 2 — Teams must decide whether to tender contracts to arbitration-eligible players. The Cubs have six such players, but only Willson Contreras ($8.7M projection) and Ian Happ ($6.5M) are likely to be tendered. While Adam Morgan ($1.3M) could makes sense, it’s hard to imagine Jonathan Holder or Joe Biagini ($800K apiece) coming back at more than the league minimum when the Cubs have so many other young relievers available.
Rex Brothers ($1.5M) hung around a lot longer than anyone could have imagined and it would be a shock if the Cubs opted to tender him a deal.
December 6-9 — The Winter Meetings are scheduled to take place in Orlando, but it’s more likely MLB execs will be taking their families to Disney World and Universal Studios sans work obligations. As awesome as it would be to have the CBA in place by these dates, I just can’t see it happening. Once viewed as the crown jewel of the offseason, communication technology and the changing landscape of the sport have taken a lot of the air out of the Winter Meetings in recent years.
This is still a great time for the baseball cognoscenti to gather for drinks and meetings, but it’s not like all kinds of big trades and free agent deals are consummated.
December 9 — The Rule 5 Draft is supposed to take place on the last day of the Winter Meetings, but a lockout would put a kibosh on that.
December 15 — This marks the end of the 2020-21 international free agent signing period, which would normally run from July through June. This year and next were pushed back to January through December due to COVID rules changes.
January 14, 2022 — This is the date by which teams and arb-eligible players must exchange salary figures. The sides can still continue to work toward a settlement, something the Cubs have done in all but two cases during Jed Hoyer’s tenure. The first of those was with Justin Grimm in 2018, which was an ill-fated effort on the pitcher’s part.
Happ notably failed to settle last season in his first year of eligibility and eventually won his case, earning $4.1 million rather than settling for something closer to the Cubs’ $3.25 offer. Based on the projection above, the erratic nature of his 2021 performance, and the club’s thriftiness, it feels like a lock that the two sides will end up in front of an arbiter yet again.
Happ’s status as the team’s union rep makes it even more of a possibility.
January 15, 2022 — Scheduled start of the 2021-22 international signing period. The Cubs are expected to land another solid group headlined by Alexis Hernandez, younger brother of this year’s top IFA signing Cristian Hernandez.
Early-to-mid February — Arb-eligible players who don’t settle will have their hearings scheduled for the first half of the month, just prior to spring training report dates. As with everything else above, this could all be pushed back by the CBA.
February 26, 2022 — Spring training games start, with the Cubs facing the Dodgers at Sloan Park to open their exhibition slate. Here’s to hoping those contests start on time and are all back to full capacity. I will say, however, that it was pretty damn nice not to have to wait in a line at any point.
March 31, 2022 — MLB Opening Day. The Cubs start the season with a three-game set in Cincinnati.
April 4, 2022 — Wrigley Field Home Opener vs. the Cardinals. This is just a two-gamer with an off-day between to account for inclement weather, after which the Cubs host the Brewers for four games
Next season feels so far away at this point and it doesn’t help that we don’t know whether and when they’ll even get these negotiations figured out. It’s like getting ready to go on a much-needed vacation only to run into construction that adds a few hours to your drive. Alas, distance makes the heart grow fonder.
The Cubs could really use an increase in fondness from their fans after a season that saw them decimate the roster and finish 20 games under .500 after looking like contenders for a minute or two. Hoyer’s got his front office team in place, now the clock is ticking on their opportunity to put a product on the field that justifies the high prices and expectations.
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