So, when Theo Epstein came in, everything was transparent. I don’t mean that he emailed every Cubs season ticket holder to let them know about a free agent signing or a trade he’s been mulling over. But, there was a clear path described to everyone that wanted to listen. Since Jed Hoyer was named president of baseball operations, there hasn’t been that same sense of transparency, or maybe that’s just what we thought?

Perhaps Hoyer has been very transparent with us, but since there is such a bigger emotional investment in this roster we haven’t really listened. Hoyer has said that he is keeping one eye on this roster, while also keeping an eye on the future. This was a change from their previous organizational plan. In the past, they were all about supporting the roster to maximize that core’s success.

What was that support? That was money, right? That was trading to supplement the talent, right? Lastly, that was attempting to sign extensions, right?

Now, it isn’t just that easy and the list of what the front office actually did was a lot longer. There was the building of one of the strongest scouting and player development programs in the game, reinventing the technical infrastructure, and bringing in franchise-changing talent. This process, while at times was difficult, led the Cubs to their first World Series. That process provided generational talent. This process finally gave fans the payoff to their emotional tie to this organization.

But Hoyer has told us this process wouldn’t follow the last. We, as fans, likely didn’t realize what he was trying to tell us. But as players started to sign elsewhere, that reality is beginning to set in. With both, Kyle Schwarber and Jon Lester joining Dave Martinez in Washington, Yu Darvish and Victor Caratini traded to the San Diego Padres, and to a lesser degree, Tyler Chatwood signing in Toronto, it is now feeling like this off-season is Hoyer’s way of gently inching a band-aid off before he tears it off in one rip next offseason.

Hoyer has pointed to the inability to sign their players to extensions as one reason this window is set to close. Guys like Willson Contreras, Javier Baez, Anthony Rizzo, and Kris Bryant have all engaged in some level of extension talks. None of them have agreed to terms. This has left the club with a somewhat disjointed feeling. A roster of gifted players, seemingly a piece or two away from being a contender, yet Hoyer is readily dismantling what was once considered a masterpiece.

Some believe that this is necessary. This core, after 2016, hasn’t achieved the success that everyone once thought. While good, they just weren’t good enough and after several postseason failures, it was time to hit reset. But is this reset based on this realization, or is it the sudden realization from ownership that they’re in a bit of a financial mess?

We have heard several times from Tom Ricketts, suggesting that spending money isn’t necessarily the best way to win a championship. He preferred building from within. Which, of course, he did. When you use your homegrown talent it is always less expensive than going out into free agency. Look at the Kyle Hendricks and Yu Darvish contracts. Darvish was earning $21m per year while Hendricks signed an extension paying an average of $13.875m annually. But, the rest of the roster didn’t follow Hendrick’s path.

The problem that is now surfacing, and astute fans have realized, the Cubs are not poised to compete today, next year, the year after, or anytime in the next several years. The team’s current minor league system isn’t filled with can’t miss prospects. Whatever prospects they do have are several years away from a possible Major League debut.

The remaining talent pool is so far away, that the talent on the current roster will be in their later 30s when they are able to contribute in any measurable way. So what do you do with the talent already on the roster, and how does Hoyer plan on putting a competitive product on the field from next year till 2026 or 2027? We’ll get to that.

“Once we get back to a place where we feel like we want to step on the gas again, we will financially,” Hoyer said. “We will be in that market again just as soon as we have a team that has the bones necessary to do that. We are at this period at the end of the window where I don’t think that would make a lot of sense right now.”

The Cubs have an opportunity to step on the gas again, and it can be real soon. First, it will take the Cubs finally agreeing to terms with at least two of their current core beyond the 2021 season. Currently, the Cubs have a CBT payroll of $138,707,000 (est. Cot’s Contracts does not have Austin Romine added just yet) and are $71,295,000 under the Competitive Balance Tax threshold. Their 2022 commitments are almost laughable, coming in only $39.5 million with about $18 million additional in arbitration. If you add another $8.5 million in players with less than three years of service, this is around $65.5 million committed in 2022. Heck, after the 2023 season Jason Heyward’s contract falls off the books, which by that point the organization only has around $8 million committed (without arbitration or 0-3 year player salaries).

Now, in the 2022 season baseball will have a new CBA in place (if there isn’t a work stoppage, which is a real possibility) so we do not know what the 2022 luxury tax would be. Owners would of course benefit from a lower CBT number, players benefit from a higher number. There will be things on the table like universal DH, which would produce more high-paying jobs in baseball. Owners will press on their unrealized profits in 2020 due to the pandemic and will want a year or two of relief before seeing total payrolls in the $220 and above range. There is a real possibility that the 2022 CBT threshold is less than the 2021 number of $210 million.

Whatever that number is, the Cubs will likely have $130-150 million in flexibility coming into next season’s free agency – if they do not sign any extensions beforehand.

The next offseason is a who’s who of MLB players and talent. Looking at the list, guys like Zack Grienke, Clayton Kershaw, Max Scherzer, Francisco Lindor, Freddie Freeman, Nicolas Castellanos, Trevor Story, Corey Seager, Michael Conforto, Noah Syndergaard, Tommy Pham, Jorge Soler, Chris Taylor, Jose Ramirez, Travis d’Arnaud and so many others will be (or could be) free agents. If the Cubs have that much money available to spend, they can jump right back into contention after the 2021 season by locking down at least two of Kris Bryant, Anthony Rizzo, and Javier Baez while peppering in several of those players.

Hoyer suggested that this offseason is about doing what’s best for the future. So in free agency, in trades, in any movements, they are looking at how this affects the future and not so much on how it helps them win in 2021. If they are to retain the better offensive players of their core, Bryant and Rizzo, they can bring in someone like Seager to play shortstop and they improve their offense significantly over the next five or so seasons (Seager averages 130 wRC+ per season to Baez’s 101 wRC+). As Seager ages, he can move to second and give way to one of the six or so SS’s currently in the Cubs farm system.

Let’s just say Bryant and Rizzo earn $25 million each per season. Their salary would pump the Cubs up to $115.5 million in total payroll. I would even suggest that Bryant entertains a one-year deal this next offseason, allowing him to post good numbers in 2021, prove it in 2022, and put himself in a much better position in 2023. This is when the new CBA will be worked out and baseball has had a full season back with fans in the stands, increasing revenue and likely ownership’s likelihood of approaching luxury tax numbers again.

Now add Seager at $25 million himself, we’re only at $140 million – essentially the current 2021 payroll.

Of course, there’s pitching. The Cubs need pitching. Hendricks is under control through the 2024 season. He’s the only pitcher the Cubs have committed dollars to after this year. The Cubs are really high on the changes Adbert Alzolay has made, and they expect that adding a slider and two-seamer will increase his ceiling quite a bit. In the past, it was thought that he could be a mid-tier starter at best, but now some are tossing around ideas that he can become a number two in a competitive rotation. That’s huge!

Cubs prospect, Brailyn Marquez is rated as the eighth-best left-handed pitching prospect in baseball. This list has guys who have already pitched well at the big league level and is a go-to who’s who of the next era. He saw one start at the big league level in 2020, but given that experience and an offseason to work, he will likely get plenty of opportunities in 2021 and be a huge part of the Cubs rotation over the next six years or so. While you always have to worry about command with young pitchers, when you have the ability to rely on a 102-MPH heater, you can fix a lot of command issues with that velo.

So we have really three pitchers to count on (perhaps) past the 2021 season. So, of course, the Cubs will need to jump into free agency to plug-and-play. They can look at one or two year guys like Grienke. Someone nearing the end of his career, but can be relied on to go out and compete. There are also guys like Marcus Stroman, Kevin Gausman, maybe Drew Smyly, and Corey Kluber. Syndergaard is another interesting option. Regardless, there 51 starting pitchers that are heading towards free agency in 2022, and the Cubs would have many opportunities to add. Some of these names can be had at reasonable rates, and even if they’re commanding large salaries the rest of the roster accommodates those additions.

Doing this will allow the Cubs to keep competing in the near-term while keeping an eye on the future. When they are trying to bridge towards another successful run once their prospects are ready to compete, they can fill a roster that is highly competitive, while remaining below any CBT numbers. This gives the front office (perhaps, more importantly, the Ricketts) financial flexibility over the next several seasons while competing.

Yes, it sucks that the Cubs biggest free-agent additions since the 2018 season have been $1.5m deals. But, when looking at the next offseason, they could be poised to make a bit of a dip to ensure there’s excitement over the next 10-15 years in Chicago.

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