Rejoice: Kyle Hendricks Is Going to be a Chicago Cub for a Very Long Time

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Rejoice: Kyle Hendricks Is Going to be a Chicago Cub for a Very Long Time

Chicago Cubs

When Kyle Hendricks first came to the Cubs as part of a broader deal for Ryan Dempster back in 2012, I remember being so completely disappointed at the outcome. The Cubs were supposed to get the “better prospect,” Randall Delgado, from the Braves, but Dempster squashed the deal and we wound up with Hendricks as an apparent fallback option.

Fortunately for me, I wasn’t writing about the Cubs professionally at the time. Unfortunately for Brett

Yesterday, at the non-waiver trade deadline (with five minutes to spare), the Chicago Cubs sent Dempster to the Rangers for third base prospect Christian Villanueva, and pitching prospect Kyle Hendricks.

But that might not be the Dempster trade that you remember 10 years from now. You might, instead, remember the Dempster trade that didn’t happen.

That trade, of course, would have netted the Cubs 22-year-old pitching prospect Randall Delgado, a pitcher who might not have single-handedly taken the Cubs to the promised land, as hyperbolists like to joke. But he would have been a heck of an incredible return for two months of Ryan Dempster.

The rest of that post is a justifiable hand-wringing of the failed pursuit of Delgado, while the rest of history is just laughing at the unnecessary concern.

This year, Hendricks and Delgado are both 29 years old, but their careers couldn’t have gone in more different directions. Delgado has never started more than 19 games in a single season (and that was all the way back in 2013) and is now a free agent. While Hendricks is a near-top of the rotation starter, who nearly won a Cy Young Award in 2016, who was the ERA leader that year, and who helped the Cubs win their first world series in 108 years. Oh, and he’s also just ensured himself a very well-deserved raise for the next six years.

Yesterday, the Cubs reached deep into their pockets to extend Hendricks for the foreseeable future – a move that was met with joy from Cubs fans top to bottom, as far as I can tell. Cubs fans like them some Hendricks, man, and their time with him was nearly over. Before this extension was signed, the Cubs had control over Hendricks for $7.405M in 2019 and something between $10-$12M(ish) in 2020 via arbitration. But then he was set to become a free agent.

Now, the rest of his career will play out like this:

2019 – Age 29: $7.405M
2020 – Age 30: $12M
2021 – Age 31: $14M
2022 – Age 32: $14M
2023 – Age 33: $14M
2024 – Age 34: $16M ($1.5M buyout)*

*The 2024 option will automatically vest if Hendricks finishes among the top-3 in Cy Young voting during the 2020 season. If he fails to meet that threshold, it becomes a club option. It’s also worth noting that his annual salaries can increase up to $3M per season (if I’m reading that correctly) based on top-10 finishes in the Cy Young vote (but again, specifics remain a little unclear).

To put this another way, the Cubs definitely bought out three free agent years, guaranteeing $63M (if you count the buyout in 2024). HOWEVER, if his 2024 option vests automatically or gets picked up by the Cubs, Hendricks will have given up four free agent years, while securing at least $77.4M in total earnings.

And if he really manages to finish among the top Cy Young vote-getters, there’s another $18M (6 years x $3M) in incentives to achieve. I doubt that’ll happen every year, but the Cubs would probably be THRILLED if it did.

Obviously, with the escalators, buyouts, and option year, calculating the *actual* average annual value for luxury tax purposes isn’t as straightforward as it often is, but for the time being, you can use $12.5M as your place-holder.

(Photo by Jon Durr/Getty Images)

And that’s great news! Although Hendricks’ luxury tax hit weakened the Cubs position this year (they were already way over, anyway), it’s likely going to be a net positive as soon as 2020. In other words, his AAV for the luxury tax calculation is likely going to be less than he’s actually being paid. And that’s good news because despite fairly moderate penalties, the luxury tax threshold has often resembled something closer to a cap. So any way the Cubs can improve their position against that limit can help with future free agent pursuits.

Although, a win from the Cubs perspective does not necessarily mean it’s a win from Hendricks’ perspective. Don’t get me wrong, he secured himself a VERY nice life for him and his family, probably … forever. But it’s also not crazy to think he could’ve done better in free agency. And I mean that even relative to the other seemingly team-friendly extensions we’ve seen this spring. Jay Jaffe (FanGraphs) even goes as far as to suggest that Hendricks could’ve done a lot better in free agency and believes the Cubs team-wide success was probably a big draw for him.

But, like, if this is where he wants to be – and if he can lock down life-changing money with some additional upside, too – no one is going to blame him.

Indeed, Hendricks said exactly as much: “This was a life decision, not just a money decision. Everything [the Cubs] bring, the way the families are taken care of, my wife, bringing in [yoga instructor Christine Schwan], just the support staff in general. If anything is ever needed, starting with Theo, I know he will try to make it happen. It’s a special circumstance to have in an organization.” Oh, baby, he’s going to win over some more fans with that one.

Theo Epstein lobbed some serious praise on Hendricks, as well: “He’s one of the most effective half-dozen starting pitchers in the game since he’s come up … The names on that list are guys on Hall of Fame trajectories. So Kyle’s in rare air for what he’s done. But more importantly, we love the process that he uses to get there, and we think it bodes well for the future.”

It’s easy to lose sight of just how good Hendricks has been since getting his call up to the Cubs – especially because he does it without a big fastball and without any emotion – but he’s been nails since 2014.

In 132 big league starts (789.0 IP), Hendricks has compiled a 3.08 ERA and 3.52 FIP. Among pitchers with at least 750 innings pitched during that stretch, Hendricks’ ERA ranks NINTH BEST IN BASEBALL:

  1. Clayton Kershaw: 2.12 ERA
  2. Jacob deGrom: 2.67 ERA
  3. Max Scherzer: 2.79 ERA
  4. Corey Kluber: 2.85 ERA
  5. Chris Sale: 2.85 ERA
  6. Jake Arrieta: 2.91 ERA
  7. Zack Greinke: 2.94 ERA
  8. Madison Bumgarner: 2.99 ERA
  9. Kyle Hendricks: 3.08 ERA
  10. Johnny Cueto: 3.11 ERA

By my count, that list contains 11 Cy Young Awards, and many, many more top-3 finishes. How’s that for good company?

We’ll have to wait and see what the future holds for the Cubs’ soft-tossing, but talented Kyle Hendricks, but he has been very good for them so far, and now, it looks like he may just be a Cub for life.

You can read more from him, his manager, and the front office at, the Chicago Sun Times, and FanGraphs.

Author: Michael Cerami

Michael Cerami covers the Chicago Cubs, Bears, and Bulls at Bleacher Nation. You can find him on Twitter @Michael_Cerami