When the Cubs and Joe Maddon parted ways at the conclusion of the 2019 campaign, more than a few people wondered who would find success again first. Looking back now, it’s safe to say things have been bumpy on both sides of that break-up, with neither side feeling all that good about things.
That is, until this year, with Maddon’s Angels entering action Monday tied for first atop the American League West at 24-13. The biggest question facing the Halos, as has been the case for some time, is: do they have enough dependable starting pitching to bring home a division crown?
That’s something Los Angeles hasn’t done since 2009 – squandering more than a decade of Mike Trout in the process. This year, though, they have a chance to get not only Trout, but reigning AL MVP Shohei Ohtani into the postseason. And, like they say: all you have to do is get in.
For that to happen, though, it seems pretty likely the Angels will need to add to the rotation. How they do so without subtracting from the big league roster remains to be seen. The farm system ranks, by almost every account, in the bottom third of the league – with Jo Adell as the main blue chip talent left – and that blue paint may be starting to peel.
Knowing the Cubs will almost certainly be sellers at the trade deadline and that the Angels need a go-to presence in that six-man rotation, I can’t help but ponder a potential reunion between Kyle Hendricks and Maddon, who, of course, managed the right-hander from 2015 to 2019 on the North Side.
Under Maddon, Hendricks emerged as a frontline starter in Chicago, taking the ball in some of the biggest postseason moments in franchise history. Adding his October pedigree and general reliability to the rotation would be a huge addition for Los Angeles, especially given the different look he’d give hitters alongside Ohtani, Noah Syndergaard, Michael Lorenzen and others.
Cubs: It’s hard to find a fair return in a trade for Kyle Hendricks
Now, the Cubs aren’t going to get Adell for a year-plus of Hendricks. It’s just not going to happen. Despite the outfielder’s struggles making the jump to the big leagues, the Halos aren’t going to dump him – at least not yet. Maybe if Hendricks was still the pitcher he was five years ago, sure – but that’s no longer the case.
That also touches on another intriguing aspect when thinking through any sort of hypothetical Hendricks trade: how do you value him? Is he the guy who put up a 3.12 ERA from 2014 to 2020 or is he the guy who’s left his sinker up in the zone far too often the last two years, culminating in a less-than-savory 4.63 mark?
Still, the Angels system is depleted – with zero Top 100 prospects, according to MLB Pipeline. That’s a tough sell for a team like Chicago, who isn’t going to trade Hendricks without getting something that can benefit them down the road. And, sorry, but a roll at the roulette table isn’t going to get it done.

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In the end, this scenario feels wildly lopsided in favor of the Angels – but, hey, stranger things have happened. Whether it comes in the form of Hendricks (or even a Drew Smyly-type arm), the Halos need help in the rotation if they want to punch their ticket to October.