Thanks to a huge May, the Cubs were in first place for much of June. An 11-game losing streak that coincided with a big Brewers run effectively ended the season, though, and now the Cubs are left with a lot of big decisions with the trade deadline set for later in the week on Friday, July 30.
The Cubs are now clearly sellers and the organization could use a bit of a reset, So it seems like some fan favorites are going to be wearing different uniforms very soon, as heartbreaking as it'll be for many in Wrigleyville.
So let's do a quick breakdown of the possibly-tradeable players.
Free agents after this season: Anthony Rizzo, Kris Bryant, Javier Báez, Zach Davies, Matt Duffy, Dan Winkler, Ryan Tepera, Adam Morgan, Robinson Chirinos
Options for 2022: Craig Kimbrel, Andrew Chafin, Jake Marisnick
Controlled only through 2022: Willson Contreras
That's a lot. No, I don't think every single player listed is going to be traded. That would be quite the flurry of moves. I do think every player listed has been or at least will be discussed in some fashion. With that in mind, let's discuss landing spots for the biggest names.
Kimbrel, as good as he's ever been, is the best reliever available and has a $16 million club option for next season that makes him an even more attractive piece. Expect Cubs president Jed Hoyer to wait until the last few hours on deadline day and watch a bidding war unfold. It would probably take less time to list the contenders who would not be interested in Kimbrel's services. Basically, every single contender able to take on money will likely be involved: Red Sox, Blue Jays (if they are still close enough to a wild card spot to buy), Astros, Mets, Braves, Phillies, Giants and Dodgers seem the most likely to be connected.
My hunch is he's gone before deadline day. He has MVP upside (he's already won it) and will be a huge boost to any lineup. He's one of the best pure baserunners in baseball and can play good defense at third base and both corner outfield spots. He's even good enough to get by in center field. He can also play first, but that's a waste of his talent.
I feel like a package with Kimbrel to the Mets is the best fit, but that doesn't mean they will be the landing spot. The Phillies would be a great spot, especially if they wanted to trust him in center field (and remember, Bryce Harper is his friend!). The Braves work. The Giants could use him at third until Evan Longoria is back and then shift Bryant around.
He might stay put. I'm not even sure how much value he has on the market. He's a good defender, but it's first base. He's a good hitter, but not a great one -- especially as a first baseman -- anymore, slashing .241/.341/.420 right now. You know where there is a good fit, though? The team that originally drafted Rizzo: The Boston Red Sox. They've gotten terrible production from first base all year and he'd love hitting in Fenway Park for a few months. I wonder about the Yankees as well.
Out of everyone listed down here, Báez seems like the most likely to stay put. Call it a gut feeling, sure, but I don't think Báez has as much value with any other team. He's beloved in Chicago -- at least on the north side -- and feeds off the crowd energy at home games. He suffered in 2020 with no fans. What happens if he gets traded, falls into one of his Bad Javy slumps and gets booed? I can't imagine that would end well. Likewise, his holes have gotten amplified to the point that I believe he's underrated now.
Teams that should be interested even if they aren't: White Sox (to play second), Mets (he can move when Francisco Lindor returns), Giants (move to second when Brandon Crawford gets back), Phillies (he can play third) and more. The Reds should be interested if they buy, but I'm not seeing that.
My guess is the Cubs head into the offseason trying to extend Contreras, but it's also possible they deal him right now with his value being higher than most on this list due to the extra year of control. The Blue Jays make a lot of sense on this front. Their catching situation is a mess and the extra year of control fits because they are surely going all in for the playoffs next year. What a lethal lineup that would be to add Contreras' bat. Might the Mariners take a look? The Astros and Braves (his brother's organization) would make sense, too.
No one is going to confuse Davies for a frontline starter, but he can be valuable as back-end depth. He has a 3.12 ERA in his last 16 starts. Teams that could be interested in something like a number five starter: Red Sox, Yankees, Blue Jays, Athletics, Mariners, Braves, Phillies, Brewers (a reunion?) and maybe even the Dodgers, though I'm guessing they'll shoot higher.
Winkler, Tepera, Chafin
Pretty much every buyer loves bullpen depth. Chafin being a lefty might separate him a bit from the field, but Tepera is having an excellent year and should land something nice in return. This might be the area where the teams looking to spend less money dive in, such as the Rays and Athletics. It's possible Winkler has been bad enough in July to not get anything back, but the other two still play.