Is now the time for the Cubs to use their payroll flexibility?

The Cubs traded away their core players rather than extend them, and now the club is light on financial commitments as well as good MLB players. Is this winter the time to strike?

Guaranteed Contracts

• Jason Heyward, RF: $44M through 2023
• Kyle Hendricks, SP: $29.5M through 2023. Includes $16M club option for 2024
• Wade Miley, SP: $10M through 2022
• David Bote, 2B/3B: $13M through 2024. Includes $7M club option for 2025 and $7.6M club option for ’26

Arbitration-Eligible Players (projections from MLBTR contributor Matt Swartz)

• Willson Contreras, C: $8.7M
• Ian Happ, LF/CF: $6.5M

Option Decisions

• Wade Miley, SP: exercised $10M club option after claiming off waivers from Reds

Free Agents

• Zach Davies, Matt Duffy, Robinson Chirinos

When the dust settled after the July deadline, the Cubs completed eight trades. Of the nine players sent packing, seven are currently free agents, Trevor Williams might be non-tendered by the Mets and the White Sox picked up Craig Kimbrel’s option. Seeing Anthony Rizzo, Kris Bryant and Javier Baez in different uniforms marked the end of an era, and now the Cubs have a bunch of extra prospects and a clean financial slate. They also have a new second-in-command in the front office behind Jed Hoyer in Carter Hawkins, hired from Cleveland. The Cubs also hired Ehsan Bokhari from the Astros as assistant GM and Greg Brown from the Rays as the new hitting coach. Furthermore, longtime executive Jason McLeod is leaving, and Randy Bush is moving into an advisory role.

Hoyer said in late September, “We plan to be really active in free agency.” Trying to decode GM-speak is always difficult, but Hoyer elaborated a few weeks later, saying, “We have money to spend this winter. But it’s really important that we do that in an intelligent way.” 

Furthermore he said, “We need to be active in a way that we feel like we’re getting the right value for the dollars we’re spending, and we’re also making sure that we’re not hindering ourselves going forward with expenditures for right now.”

Hoyer also cautioned against “winning the offseason.”

MLBTR projected the top 12 free agents to each receive contracts of at least five years, with the exception of a record-setting three-year deal for Max Scherzer. When I try to translate spending money “intelligently” and “not hindering ourselves going forward,” I take it to mean that the Cubs won’t sign any of those top dozen or so free agents. Hoyer has stated that the Cubs “have a lot of holes to fill on this roster,” which is a euphemism for a lack of present MLB talent. The Cubs will shop at the top end of the free agent market again, but I don’t think it will be this winter.

So what will the Cubs do? Hoyer made it clear that adding pitchers, particularly those with strikeout ability, is the team’s top priority. Why, then, did the club commit $10M to 35-year-old lefty Wade Miley, whom the payroll-cutting Reds cast off after a fine season? Miley possessed a 90 mile per hour fastball and the sixth-worst strikeout rate in baseball this year among those with at least 160 innings. The answer is that Miley is still a solid pitcher, the only cost was his salary and it’s a one-year commitment. For a team with no rotation locks beyond fellow soft-tosser Kyle Hendricks, the Cubs took the opportunity that fell into their lap. Miley’s best attribute is his ability to generate weak contact, as he ranked fourth in baseball in average exit velocity.

The Cubs may yet add two or three starting pitchers to the rotation. As far as potential free agent targets, let’s cross off those seeking five-plus years or an immediate shot at a championship. We’re left with Carlos Rodon, Eduardo Rodriguez, Alex Wood, Yusei Kikuchi and Jon Gray atop the strikeout leaderboard. We believe Rodriguez may require a four-year deal — plus Boston’s qualifying offer means the Cubs would sacrifice their second-round draft pick. Noah Syndergaard comes with that same draft pick problem, if he even reaches the open market. Rolling the dice on Rodon makes some level of sense, in that the Cubs wouldn’t be hampered by a deal anywhere from one to three years, and he offers possible ace-like pitching without a $100M commitment if the club rolls the dice on his health. Rodon is the moon shot option, while Wood, Kikuchi, Gray and James Paxton are safer choices. Free agency also offers pitchers with decent velocity if not the strikeout rate, like Steven Matz, Garrett Richards and Anthony DeSclafani.

The trade market is also an option for the Cubs, which could offer one year of Willson Contreras, deal away some of their prospect capital or just take on an unwanted contract. Strikeout pitchers who could be available in trade include Blake Snell, Yu Darvish, Tyler Mahle, Pablo Lopez, Sonny Gray, Frankie Montas, Zac Gallen, Sean Manaea, Chris Paddack, Chris Bassitt, Caleb Smith and Luis Castillo. The Rays’ Tyler Glasnow makes sense for the Cubs, even though he won’t be recovered from Tommy John surgery until the 2023 season. Indeed, such a trade was considered back in July.  The Tigers’ Matthew Boyd, who underwent flexor tendon surgery in September, may be non-tendered by the Tigers and also makes sense for the Cubs. Back when the Cubs had some money to burn, they signed Drew Smyly to a two-year, $10M deal off Tommy John surgery with an eye entirely on the second season.

Three of the best trade targets are on the Reds, which may be reluctant to trade a starter to the division-rival Cubs in addition to Miley. The idea of the Cubs reacquiring Darvish one year after his trade somewhat kicked off their rebuild is too amusing not to mention. After the Cubs shipped Darvish and backup catcher Victor Caratini to San Diego for four low-minors prospects and Zach Davies, Darvish went on to post a 2.44 ERA through the season’s first half. He got blasted (mostly by home runs) in the second half to the tune of a 6.65 ERA. Darvish is owed $37M over the next two years, and the Cubs suddenly have the payroll flexibility the Padres desire. Just saying, it’d be fun to see.

The bullpen is another clear need for the Cubs, which are left with guys like Codi Heuer and Rowan Wick atop their depth chart. A few cheap free agent investments make sense here.

The Cubs’ infield is mostly set, with Contreras at catcher, Frank Schwindel at first, Nick Madrigal at second, Nico Hoerner at short and Patrick Wisdom at third. While Schwindel (age 30) and Wisdom (29) aren’t likely long-term solutions, they’ve at least earned at-bats in 2022. The Cubs also have to see if a Madrigal-Hoerner double-play combination has staying power.

With one year of control remaining on Contreras, the Cubs enter into the familiar “extend or trade” territory that led to their July sell-off. The free agent market is weak at the position, and teams like the Yankees, Guardians, Rangers, Marlins and Giants might be seeking catching help.

Ian Happ avoided a possible non-tender by posting a 147 wRC+ over the season’s final two months. He figures to hold down left field, while Rafael Ortega can keep center field warm until the Cubs deem top prospect Brennen Davis ready. In right, there’s Jason Heyward and the $44M owed to him over the next two years. After a brutal 68 wRC+ in 2021, the Cubs probably can’t justify a roster spot for Heyward through all of ’22 unless he manages at least league-average hitting. While the Cubs could explore a potential bad contract swap, they’re in more of a position to take on dead money as a means of accumulating yet more prospects.

One outfield addition that could make sense for the Cubs is right fielder Seiya Suzuki. It’s nearly impossible to project what level of contract Suzuki will require if he’s posted by the Hiroshima Carp, but he’s only 27 years old and one of the best players in Japan. Signing him would be akin to the club’s $30M deal for Jorge Soler, which occurred about eight months into Hoyer’s tenure with the team.

We’re about to embark on a free agency experience unlike anything we’ve seen in recent years, with a probable lockout followed by a compressed signing period. If some players fall through the cracks in that scenario, the Cubs are well-positioned to make opportunistic strikes with one-year offers. With Heyward, Hendricks, Miley, David Bote, Contreras and Happ, the Cubs have an estimated $63.7M committed for six players. As a team capable of sustaining a payroll in excess of $200M, the Cubs are a sleeping giant right now. In reference to the Giants, Hoyer said, “They certainly didn’t win the offseason last year. They won the season.”  While I can say with certainty the Cubs won’t win 107 games in 2022, it’s clear that the team would prefer to avoid the top end of free agency this winter, become a surprise contender and then look to flex its financial muscle.