Two Cubs World Series legends could be poised to ride into the sunset this winter

We've officially hit the retirement watch portion of the baseball season, with MLB.com singling out nine players who could hang them up this winter. The list is notable for Chicago Cubs fans for two reasons: and their names are Jason Heyward and Kyle Hendricks.

Heyward recently latched on with the Houston Astros after being cut loose by the Los Angeles Dodgers - and it seems likely he'll get a chance at another World Series ring given Houston's 98.8 percent chance to make the postseason, according to Fangraphs. The veteran plugged right into the Astros outfield mix and seems quite content with his new home for the stretch run here in September.

"Man, that's an honor. A team...who has the rings, has the history of finding a way to get it done. That's something always fun to be a part of."

Jason Heyward on joining the Astros

Heyward turned in his strongest offensive showing in years last season in Los Angeles, slashing .269/.340/.473 - good for a 119 OPS+, his best mark since the shortened 2020 campaign with the Cubs. He parlayed that into a one-year, $9 million deal with the Dodgers this winter but he came up short of expectations in his second year with the club, ultimately leading to the decision to designate him for assignment.

Of course, back in 2016, although he never lived up to his franchise record contract at the plate, Heyward played a key role during that window, bringing home Gold Glove awards for his work in right field and delivering the infamous rain delay speech during Game 7 of thet 2016 Fall Classic. That speech alone made him worth every penny, but as the years passed, even that couldn't stem the frustrations from fans.

Kyle Hendricks still grinding it out for the Cubs down the stretch

As for Hendricks, he seems to be winding down what's likely to be his final season with the Cubs - the only MLB team he's ever pitched for. Despite a solid spot start on Tuesday in lieu of the injured Justin Steele, Chicago lost his latest appearance after the offense went missing against the Pirates. But disappointing 2024 season aside, there are few pitchers in Cubs history who have been more impactful than Hendricks.

Although he's never been an All-Star, Hendricks brought home the ERA title in 2016, working to a 2.13 ERA in 190 innings of work that year. He carried that dominance into October, shutting down the Dodgers in the NLCS - including in the pennant-clinching win at Wrigley Field - and in the World Series against Cleveland.

From 2014 to 2020, Hendricks was quietly an incredibly reliable starting pitcher in the league, pitching to a 3.14 ERA in over 1,000 innings of regular season work. Although he's never been the same pitcher since, there's no questioning the role he played during the golden era of Chicago Cubs baseball.

Personally, I think both guys will have a chance to latch on somewhere this winter, if only on a minor league deal. But if this is the end of the road, it was quite the journey for both. A pair of World Series rings, a third-place Cy Young finish, one All-Star nod and five Gold Gloves. Not a bad combined resume, if you ask me.