Would a Cubs Trade of Kyle Hendricks Slam the Contention Window Shut?

Kyle Hendricks in Game 7 of the 2016 World Series by Arturo Pardavila III. CC BY 2.0

“In this job, you always have one eye on the present and one eye on the future. ‘And the truth is that, given the service-time realities that I mentioned, I think that eye might be a little bit more focused toward the future than usual. But that doesn’t take away from the goal. And, like I said, the goal is always to make the playoffs and give the organization a chance.’’

Jed Hoyer via Russell Dorsey of the Chicago Sun Times (emphasis mine)

Theo Epstein left an indelible mark on the Chicago Cubs organization. Since his first press conference in 2011 when he deftly laid out his vision for ultimate success, to his final moments handing over the reigns to his protégé, Jed Hoyer, this era will always be “Theo’s Cubs”. To many fans this winter already feels like a momentous shift in organizational philosophy. In many ways, that’s correct. Fan favorites like Yu Darvish, Jon Lester, and Kyle Schwarber are already set to wear other uniforms. Other core players such as Kris Bryant and Willson Contreras are frequently named in trade talks. Simply put, the contention window that Theo spoke so often about is closing. Jed Hoyer now speaks about keeping an “eye on the present and one eye on the future”. The Cubs are at a crossroads. In a weak NL Central, this team (while significantly flawed) may still be in the running for the best in the division. However, despite the wholesale changes this offseason and the near future, there is one move that would be so impactful to the organizational trajectory that it would render Cubs President Jed Hoyer’s statement that “the goal is always to make the playoffs” completely moot.

Concerning 2021: If the Chicago Cubs trade Kyle Hendricks, it creates a situation where the contention window isn’t just shut, the house has fallen down, and you’re selling your lawnmower in the middle of the winter to anyone with cash in their pocket.


I’ll admit that the previous statement is dramatic. There is always a pathway that any one player in an organization could be traded for other talented players, but in a realistic environment where front office executives often experience “groupthink” and all utilize player valuation models, it is unlikely that a Kyle Hendricks trade returns several premium MLB ready players. The 2021 Chicago Cubs sans Kyle Hendricks is one with a significant deficit in quality starting pitching. It can’t be overstated how bad the National League Central is, but a Professor-less Chicago Cubs team is not a competitive one in 2021. Any Kyle Hendricks trade likely requires the Cubs to seriously consider trading any non-Happ/Alzolay player on the roster. In this article I’ll examine the effects three different trade scenarios could have on the Cubs organization. Each scenario includes general types of players in return for Hendricks.

Disclaimers: I will not be creating “mock trades” with various teams. I operate on the assumption that all mock trades are bad, including mine. They are. And even though I’ve historically spent a lot of time on them as a fan, I’ll avoid them here. This post will examine three unnamed team/player scenarios and how each may affect the Chicago Cubs organization going forward. If you want to spend way too much time on this you can probably figure out the players or teams that formed the genesis of the ideas, but it is not meant to act as trade rumors or mock trades.

Scenario 1: MLB-Ready Talent

  • Unestablished righthanded starting pitcher who rates as a Top 50 overall prospect. Brief success at the major league level. A very strong bet to be a successful #4 starter.
  • CF/COF prospect who has small sample in big leagues. Appears ready to be an average regular starting player. A power over hit profile who should be able to stick in CF. He’s a Top 125 talent.
  • Bounce-back candidate corner outfielder. Strong year in 2019, but poor 2020. No options remaining, but a weak-side of the platoon candidate at minimum.

Scenario 1: MLB-Ready Talent

If Jed Hoyer is completely serious and the Cubs play to compete for a division title next year, it’s impossible to simply replace Kyle Hendricks. Even setting aside his production, the intangibles that Kyle brings through setting the tone for the other starters and implementing the run prevention game-planning is incalculable. However this first scenario at least attempts to replicate the production with a SP ready to step into the rotation and two outfielders who should be able to get at-bats in 2021.

The ceiling is the lowest of the three scenarios, but the near-term production is the highest. It is at least plausible for the Cubs to compete if everything breaks right in 2021. While it is unlikely, there is the possibility the Cubs switch out a starter, add to the outfield, and could repurpose Kyle Hendricks’s very reasonable $14 million in this scenario.

Scenario 2: Supplementing the 2022-2023 Wave

  • Right handed starter with a three pitch mix, but carries some reliever questions. This is a top 75 prospect who could be ready to make an appearance by the end of the 2021 season, but impact on a major league club is likely to be in 2022.
  • Young C prospect who has had success in full-season ball and is likely to start 2021 in high A. He’s displayed an above-average ability to make contact while also providing signs he may add more pop. Could be up in 2023 and a strong candidate to be on Top 100 lists next year.
  • Recent college RHP drafted in the 2nd round, but mocked in late first round. Another starter with reliever question marks. He’ll flash several plus pitches. Timeline for arrival is 2023.

Scenario 2: Supplementing the 2022-2023 Wave

With a core group of Davis, Amaya, Marquez Strumpf, Morel, Weber, Jensen, (R.) Thompson, and possibly Franklin, the Cubs boast a wave of talent that isn’t far from Wrigley. The majority of these players will get time in AA or beyond next year. This scenario effectively resets the team in 2021. There is minimal production expected from this group of prospects coming in next year, but the Cubs would acquire two likely Top 100 prospects to go along with a college SP that should get High A innings in 2021. The catcher prospect probably feels redundant with Amaya in this wave, but it appears the Cubs are building out the position in the minor leagues to go along with the cadre of shortstop prospects. This catcher is a year or so behind Miguel Amaya and a complement, not his replacement.

More deals of players with expiring contracts in 2021 and 2022 would be expected with this scenario. The money saved off Kyle’s salary could be reallocated, but, if it was, it would be for flippable assets rather than multi-year deals.

Scenario 3: The Yu Darvish Redux

  • A top 100 prospect and a RHP who could be up in 2022
  • CF who received a top signing bonus in 2019 international free agency period. He had a very successful instructional league and has a very high ceiling. Likely a 2024 timeline.
  • Prep righthander from the second round of the 2020 draft. He’s years away but boasts strong offspeed pitches.

Scenario 3: The Yu Darvish Deal Redux

I firmly believe the talk that the Cubs were very interested in Luis Campusano of the Padres (in the Yu Darvish deal), but backed off later in the negotiations and settled on two more teenage prospects from the Padres. Campusano represented a talented player would could impact the team within the next two years. The other two players in the Darvish deal were clearly added to build out a 2024-2025 core in the lower minors.

This deal would be a similar model to what (I’m piecing together) formed the basis for the negotiations for Yu Darvish. The goal would be to add one player who could impact the team soon and then multiple players who would continue to build out the deep wave in the low minors. The two players would add another OF and a pitcher. While You Can’t Have Too Many Shortstops, it felt redundant to add another to this group.

The effect of this deal is simple: 2021 is not competitive and there isn’t substantial talent added to the 2022-2023 core. Of all the scenarios, this one is the most reliant on further deals.

What deal would you pick?

I’ll repeat that none of these scenarios is ultimately fulfilling, but each could be similar to a pathway the Cubs take. I would like to believe trading Kyle Hendricks would only happen if a team offered a king’s ransom, but the more you hear Kyle’s name in reports, the more likely the Cubs are seriously listening to offers on the Professor. Teams are in search of impact talent in the rotation on reasonable deals and it’s hard to do better than a playoff tested Top 20 overall pitcher in Hendricks. As for the Cubs, perhaps no other player in the organization dictates future decision making like what Chicago does with Kyle Hendricks.

Published by

Greg Zumach

Following the Cubs minor leagues and the MLB draft has been my passion since I became a fan. I try to focus on deeper dives into players along with MLB Draft content throughout the year.

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