A First Look at This Year’s Robust Free Agent Class and Whom the Cubs Might Target

The regular season has five days left, and then there’s that whole postseason thing. It’ll still be another five weeks before we actually reach free agency.

But I don’t think Jeff Passan is jumping the gun by getting into the top free agents today. It’s a big ole group of free-agents-to-be, particularly deep even if not particularly top-heavy, and I’m certainly ready to start digging in before this season even ends. Must be because, you know, Cubs …

Here’s where Passan put things together to kick off the “offseason”:

As Passan notes, the biggest framing device here for every early offseason discussion of free agency is the looming expiration of the Collective Bargaining Agreement:

Baseball’s collective bargaining agreement expires Dec. 1, and while the league and players’ association have engaged in conversations on a new deal, the possibility of the current basic agreement expiring and prompting a work stoppage is very real.

This makes the period between the end of the World Series and Dec. 1 entirely fascinating. How aggressive will teams be? How willing to strike a deal before the new terms governing the game will players be? Multiple contract extensions are expected in the coming weeks, sources told ESPN, showing a willingness by both parties to barter before anyone knows where payrolls are likely to end up. At the same time, during a lockout everything related to major league transactions would be frozen. No signings. No trades. No movement on the big league side.

Most, I think, do expect at least some period of lockout. So that has led me to suspecting we’ll see very little free agent activity in November, but it’s interesting that Passan notes hearing of a lot of extension talk. That’s a little bit easier to see than an early free agent signing, since there’s already a relationship in place. Still, it seems so risky for both the player and team to want to step to the table without knowing how the finances of the game might change so fundamentally (to say nothing of the rules, roster construction, service time, draft pick compensation, etc.). I tend to think the extensions we see will look like the handful we’ve seen over the last month – very short-term deals for guys who weren’t otherwise going to get long-term deals anyway. The kinds of deals that are clearly designed to keep both sides comfortable and happy however the CBA negotiations go.

As for the free agent list, Passan gets into nearly 100 names, broken down by tiers. You already know the eight names in the top tier – Javy Báez, Kris Bryant, Freddie Freeman, Kevin Gausman, Robbie Ray, Max Scherzer, Marcus Semien, and Trevor Story – and you also probably already know that the Cubs are unlikely to aggressively pursue many, if any, of those guys. I could make arguments for Báez, Gausman, Semien, and Story, but they would all involve phrases like “if his market doesn’t develop,” and “if the Cubs think they can get a relative bargain.”

Still, you can make a whole lotta hay in this free agent class if you’re adding $70 to $90 million in 2022 payroll (which, by the way, would STILL leave the Cubs something like $50 million UNDER the luxury tax!).

The second tier definitely includes some guys I’d love to see the Cubs go after – Nick Castellanos, Marcus Stroman, and Noah Syndergaard chief among them – but we’ll see. Castellanos and Syndergaard may wind up with Qualifying Offers, so that’s an issue to be addressed. Stroman is ineligible for one, but he’s a 30-year-old coming off one of his best seasons, and in a market that has very few starting pitchers without a lot of questions. I could see him winding up in the five-year-deal range, and I don’t think the Cubs are going to be going there. Four years at a strong AAV? Yeah, maybe. I mean, I’d love to see it. Stroman is fun. And good.

Otherwise, though, I continue to focus on starting pitchers and interesting positional opportunities just about anywhere. I figure the Cubs will, of course, add some relievers, too, but I don’t think it will be an immediate focus of the free agent dollars. Instead the Cubs will try to keep finding “wins” like Andrew Chafin and Ryan Tepera.

Tier three is loaded with interesting guys who could wind up going for short-term, high-AAV deals (the kind I think the Cubs will really be targeting). Among the most interesting: Michael Conforto, Anthony DeSclafani, Jon Gray, and Eduardo Rodriguez.

Tier four features a surprising appearance by Anthony Rizzo, which is facially kinda funky given that the tier also features Brett Anderson, who has managed 90.0 mediocre innings this year. Apples and oranges, I guess, which happens when you’re trying to create tiers. I won’t holler at Passan too much.

As for the names in tier four that stand out to me: Dylan Bundy, Mark Canha, Johnny Cueto, Danny Duffy, Kwang Hyun Kim, Corey Kluber, Steven Matz, Andrew McCutchen, Tommy Pham, Kyle Seager, and Jorge Soler (yup, him!).

Check out the whole thing for yourself, and start scratching out your realistic wish lists. Just make sure it’s really, really heavy on starting pitchers …

written by

Brett Taylor is the Lead Cubs Writer at Bleacher Nation, and you can find him on Twitter at @BleacherNation and on LinkedIn here. Brett is also the founder of Bleacher Nation, which opened up shop in 2008 as an independent blog about the Chicago Cubs. Later growing to incorporate coverage of other Chicago sports, Bleacher Nation is now one of the largest regional sports blogs on the web.

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