10 Realistic Free Agent Targets for Transitioning Cubs to Pursue This Winter

Many believe the Cubs will enter next season with a cheap roster that looks very similar to what we’re seeing now, just with a few more castoffs and prospects added to the mix. Some believe Jed Hoyer will be able to use the budget surplus from traded players and an abject lack of extensions to pursue top free-agent talent. The truth of the matter is that we’re probably going to see the front office seeking out value deals that make the team slightly more interesting without creating any long-tail financial obligations.

“We plan to be really active in free agency,” Hoyer told the media last week. “We plan to spend money intelligently, I think that’s probably the easiest way I can say it. Obviously, we’re scouting that market heavily. We’re going to analyze that market heavily.

“There’s offseasons when free agency is something you do a little bit of, and obviously this year we’re probably going to be a little more active than usual to fill out our roster because we have a lot more open spots. Obviously, we’ll be active in free agency, but we want to do it in a thoughtful and intelligent way.”

You don’t need to be fluent in exec-speak to read between the lines and see that Hoyer will be seeking value while also prioritizing quantity over quality, or at least putting the two on an equal plane. So the “active” part of the whole thing is likely more of an indication that they’re going to be picking up several players for whom the market never really develops rather than engaging in any bidding wars.

Think of it like combing the grocery store for perishables that have been marked down because they’re nearing their expiry. While Hoyer probably won’t wait until spring training to do all of his shopping, it’s entirely possible he and many of his colleagues will use the CBA’s completion as the green flag for any significant activity. After all, it’s only after that gets done that they’ll know for certain what rules will dictate next season and beyond.

Even once things are ironed out, assuming that all happens without a protracted battle that results in a work stoppage, it may be foolish to anticipate the Cubs going big on marquee stars. Not only would they have to pay a premium to lure those players at this point, but there are enough potential impact prospects matriculating through the system that Hoyer won’t want to block their progress with someone who’s locked in for another half-decade or longer.

Their current competitive situation also likely rules out the possibility of signing Max Scherzer or even Justin Verlander, both of whom will surely limit their suitors to win-now contenders. That’s too bad because Scherzer would be the kind of addition who, like Jon Lester in 2015, signals to his peers that Wrigley Field is the place to be.

With that in mind, I wanted to take a look at 10 players the Cubs could and should realistically target this winter. Sahadev Sharma laid out a good bit of context last week in The Athletic and Jeff Passan recently published a tiered list of free agents, so those two pieces colored my thought process here and are worth your time to check out either before or after reading what follows.

Passan’s top two levels feature 10 players, none of whom realistically figure to be in the Cubs’ plans. So that eliminates Carlos Correa, Corey Seager, Javier Báez, Kris Bryant, Robbie Ray, Kevin Gausman, Trevor Story, and a few others. What I’m saying is that you can cross off most reunions and the upper crust of the starting pitching and shortstop markets right off the bat.

Okay, so who’s left?

Nick Castellanos (Tier 2) has all but admitted he’ll be opting out of his deal in Cincinnati and he’s continued to profess his love for playing at Wrigley. There might be enough mutual interest to get the Cubs to spend a little more than they’d like over a longer period of time while also getting Castellanos to forego the potential for more money on a more immediate contender. The possibility of the universal DH also means he wouldn’t really be blocking Brennen Davis, who should be in Chicago next year.

Noah Syndergaard (Tier 2) finally returned to the mound Tuesday night after missing all of 2020 and nearly all of this season due to Tommy John surgery. He threw just one inning as the starter for the Mets in the second game of a doubleheader, but his fastball averaged 96 mph and he struck out two while facing the minimum. He’s probably a lock for a qualifying offer, the existence and function of which is still up in the air, though he might look for a bigger short-term deal elsewhere. The Cubs have more than enough financial flexibility to swing that with little to no impact on the distant future.

Michael Conforto‘s (Tier 3) line this season looks like Ian Happ‘s, just with a little better plate approach and a lot less slugging. But that also means he could be looking for a pillow deal in the hopes that he can parlay a rebound into a bigger contract heading into his age-30 season in 2023. This would be akin to the Joc Pederson move in that sense, only Conforto is a very different kind of hitter.

Alex Cobb (Tier 3) is 34 and might be looking for a softer landing spot, but the Cubs need to add two starters and aren’t looking to break the bank doing it. Lord knows Cobb checks the boxes Hoyer tends to look for in pitching acquisitions: Injury history, former Ray, former Oriole, past his prime. I’m not really even joking there. If Cobb doesn’t have better offers, the Cubs might give him a chance to parlay a strong first half into a move to a contender.

Kendall Graveman (Tier 3) would make for a pretty ironic move after the Cubs failed to pick up his option in what served as a harbinger of things to come. Though his 2020 season didn’t offer much to get excited about, the 30-year-old has found new life and added a couple ticks to his fastball this season as a high-leverage reliever. While they don’t really need bullpen help, the Cubs might be able to lure him with the opportunity to start if that’s something he still wants.

Jon Gray (Tier 3) was selected just one spot behind Kris Bryant in the 2013 draft and he’s been a perfectly pedestrian pitcher for the most part ever since. His 2017 and ’19 campaigns stand out, particularly when you consider the Coors Field factor, but the 29-year-old has only made 30 starts once and has never eclipsed 173 innings in a season. This could work if he’s not getting what he really wants elsewhere.

Steven Matz (Tier 4) is exactly the kind of player who fits the description Hoyer laid out above because he’s a solid starter who doesn’t figure to draw a ton of interest or a very big salary from a team willing to overpay for him. The Cubs could use a lefty starter and Matz has the kind of mid-90’s velo they have lacked in the rotation of late.

Danny Duffy (Tier 4) will be 33 in December and has a limited market due to his age and injury history, so there’s no way he lands anything more than a show-me deal. But he’s a lefty who showed a little juice with a 94 mph fastball this season and that’s something the Cubs are sure to like if the price is low enough. He feels like a flippable starter should Hoyer be going that route.

Jorge Soler (Tier 4) isn’t the first player who comes to mind when you think about bringing back former Cubs, but he could fit in nicely with the DH back in place. After a brutal first half that saw him bat .190 with 13 homers for the Royals, he has batted .265 with 12 homers for the Braves. He has also cut his strikeouts to just 18.5% with Atlanta and possesses the kind of prodigious power that could help to offset what will be a more contact-heavy approach for the Cubs.

Kyle Seager (Tier 4) is Corey’s brother and clearly isn’t going to command the same sort of attention, which tends to happen when you’re 34 years old. Though he always had decent pop, the elder Seager went with the Joey Votto approach this season and exchanged a little contact for power. The result was career highs in homers (35), RBI (100), and strikeout rate (24%). A lefty batter, Seager could platoon with Patrick Wisdom or push the rookie home run leader to the outfield more frequently.

There are dozens of other names I could have added to this list, many of whom are probably more realistic or better fits in either your eyes or Hoyer’s. Circumstances will be different in a month than they are now and they’ll be different still once we get serious about discussing the impact of the CBA, so this is really just about creating some conversation around a team that otherwise isn’t giving us anything to talk about.

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