Cubs Listed Among Best Fits for 5 of Top 7 Free Agents, Plus 5 More in Top 40

It’s fitting that the contract predictions we’re about to cover came out on Halloween because Jim Bowden has been masquerading as a journalist for quite a while now. That’s overly harsh, but I have to keep up the schtick here. Despite shortcomings in other areas, the redeeming quality of the former MLB general manager’s columns for The Athletic is his ability to peg contract terms for free agents. There’s a joke in here about correctly estimating international bonuses, but I’ll avoid that for now.

Even though a lot of folks don’t believe it, the Cubs are going to be aggressive this offseason when it comes to adding free agents. I’d be willing to bet they exceed the first luxury tax penalty threshold of $237 million, though they’ll probably view the second level of $257 million as a hard cap. Jed Hoyer knows he needs star power to push his team into contention, and those players don’t come cheap.

More importantly, Tom Ricketts knows the Cubs need a bigger draw to get butts in seats and Wrigley and to sell Marquee subscriptions. As MLB’s streaming regulations continue to evolve, the market for the Cubs’ flagship station could explode to the point that it more than covers any contract the front office can negotiate. I don’t know how many fans are paying the $20 per month for the service, but let’s just say very optimistically it’s half a million.

That’s $10 million per month for the year, assuming people don’t cancel it during the offseason. At $120 million annually, those subscriptions would be about 33% more than the Cubs earn each year from Marquee’s rights fees. But if the team goes big this winter and makes a postseason run, the subs are going to jump. Removing blackouts and allowing teams to sell their streaming services nation- and worldwide would result in a massive leap from there.

It’s not inconceivable for Marquee to increase its subscriber base tenfold with the right confluence of events. Do you think $600 million a year from those fans would be enough to allow ownership to spend more freely? You’re damn right it would. Of course, that confluence is predicated largely on spending big to continue building on the momentum from this past season.

Which brings us to Bowden’s list of the top 40 potential free agents — many of whom won’t even be free agents — and the Cubs’ connection to five of the first seven listed. Keep in mind that no one is saying the Cubs will be in on all of these players or that they’ll even sign any of them. This is just a matter of predicting contract values and listing best fits.

That said, being among the best fits requires a belief that the teams in question will at least be willing to entertain a massive deal or two. Let’s get to it, shall we?

1) Shohei Ohtani – 10 years, $477 million
There are risks with him having his second elbow reconstruction since coming over to MLB, which limits him to just DH’ing next season, but Ohtani is the one player you can almost guarantee will earn his club more than his contract. Remember those Marquee subscription numbers? Imagine the revenue if the streamer is able to sell its subscriptions abroad.

Ohtani would be the biggest superstar on the North Side since Sammy Sosa singlehandedly allowed the Cubs to inflate their ticket prices from league-average to the highest in the NL. There’s going to be a ton of competition for his services and I don’t think the Cubs have much of a chance, but they should pull out all the stops just the same.

2) Yoshinobu Yamamoto – 7 years, $211 million
It’s not often that 25-year-old aces hit the market, but that’s the case here as the best pitcher in Japan’s NPB comes to the States. Yamamoto is going to get top-of-the-rotation money, which could push him out of the Cubs’ price range given their current needs. Still, this is the kind of pitcher who could further solidify a fairly decent group that lacked dynamism in 2023.

4) Aaron Nola – 5 years, $125 million
This prediction actually seems pretty light based on the eight years and $200 million Nola was reportedly seeking last offseason. But the righty didn’t have the best walk year and probably won’t come close to the figures Bob Nightengale suggested, which shouldn’t come as a surprise. With the Cubs presumably looking for more value outside of a potential Yamamoto pursuit, other teams will be more willing to outspend them on Nola.

6) Cody Bellinger – 6 years, $144 million
This also feels light to me, both in years and total value. If Bellinger actually ends up at this figure, it’s a no-brainer for the Cubs to bring him back. The big problem, however, is that he may end up waiting until the last minute to sign. That’s especially likely at a lower figure than he’s targeting, and the Cubs can ill afford to center their offseason on a late decision.

7) Matt Chapman – 6 years, $127 million
A disappointing offensive campaign will hurt his asking price, but Chapman is one of the best defensive third basemen around and he could easily rebound at the plate. I mean, just look at Bellinger. The question for the Cubs is whether to prioritize Chapman as their key free agent addition after doing so with Dansby Swanson last winter. Both are excellent players with top-notch gloves, but neither is a bona fide star.

12) Michael Wacha – 1 year, $16 million
He probably won’t reach free agency because the Padres have an option on him, so I’m not really sure why this is even here.

14) Marcus Stroman – 1 year, $21 million
Rinse and repeat.

20) Whit Merrifield – 2 years, $16 million
He’s not actually linked to the Cubs…yet.

27) Jeimer Candelario – 2 years, $15 million
Though he fell off badly after a hot stretch to begin his second stint with the Cubs, Candelario would be a steal at this price. The Cubs need help at both corner infield spots and bolstering them at such a low cost would leave plenty of flexibility.

29) Kyle Hendricks – 2 years, $25 million
The Cubs aren’t the only team listed as a fit, but they’re reportedly already working on an extension with him. Jesse Rogers refuted that report, saying it’s more likely the Cubs simply pick up their option on Hendricks, but he’s still in Chicago either way. For what it’s worth, I predicted two years at $24 million with some performance bonuses.

31) Wade Miley – 1 year, $13.5 million
Dude, no. As good as Miley has been at limiting hard contact, he’s another soft-tosser with very little margin for error. It might be a different story if the Cubs had a ton of velocity in the rotation and just needed to fill it out for a year, but that’s definitely not the case.

Welp, that’s all for now. It’s very interesting that the Cubs were name-checked heavily up toward the top and then were only connected mainly to current members — and a former member — of their roster at very low AAV and/or years. Maybe it’s just coincidence, but I think Bowden is onto something with the idea that the Cubs are indeed going to try to make a splash or two at the top end of the market while offsetting that with cheaper additions.

As hard as it is to see them going full Rangers with $800 million in external acquisitions, there’s something to be said for having more young talent pushing up to the bigs. Actually making good on development, especially with pitchers, will enable to front office to offset those long-term contracts.

I also believe they’ll be in on the Juan Soto trade talks, though that deal coming to fruition could preclude at least one big pursuit elsewhere. Some of you will no doubt remain convinced that Hoyer is going to do nothing this winter, or perhaps that he’ll do just enough to make it look like the plan is to spend on a competitive club. With just a few days left ahead of the offseason’s official start, I guess we’ll find out one way or the other soon enough.