With the World Series set to begin Friday, the Cubs may be just days away from their offseason truly getting underway.

As many holes as the Cubs have to fill this winter, at the top of the priority list is going to be starting pitching. Yes, the rotation was exceptional in the second half to the tune of a 2.89 ERA (the third-highest across the majors). But the first half saw them deal with injuries and inconsistency from their starters that the depth they had couldn’t withstand, and the Cubs understand no team can ever have enough starting pitching in their system.

“We’re actively looking for quality innings, pitchers we feel like we can work with and potentially make better,” president of baseball operations Jed Hoyer said during his season-ending press conference. “We’re far from done when it comes to building a pitching staff.”

The Cubs are expected to be players in the high-end starting pitching market, and combining a bonafide No. 1 starter with Marcus Stroman and Justin Steele would give the Cubs a notable top three. Kyle Hendricks, Hayden Wesneski and Keegan Thompson are among the in-house arms who could round out the rotation, and beyond them, there’s more depth in the system with the likes of Adrian Sampson and Javier Assad ready to fill in for a start if need be.

But that’s not where the Cubs will stop this winter, nor should they. As Hoyer said, he wants more pitchers who can provide “quality innings.” That could mean signing a mix of a top-of-the-rotation starter, another backend rotation piece and a relief arm or two built up for multiple innings. That would feel like a successful offseason as far as adding to the team’s starting pitching depth, and as long as they aren’t giving out exorbitant contracts in an attempt to win a World Series next season while sacrificing what could happen in 2024 and beyond, that would match up with Hoyer’s idea of “intelligent spending.”

And if that’s the goal, there are a pair of 2022 Cubs who will soon be hitting the market that the Cubs should consider bringing back.

Drew Smyly and Wade Miley, both left-handed veteran starters, are set to be free agents the day after the World Series ends. Miley’s contract is up after the Cubs picked up the $10-million tab on the last year of his deal when they claimed him off waivers from the Reds, and Smyly’s $10-million mutual option for 2023 isn’t expected to be exercised.

As far as talks for a reunion with either of the two veterans, it seems the ball is in the Cubs’ court. At various points throughout the season, both Smyly and Miley stated how much they enjoyed being in the organization. And after both of their final games of the year on Oct. 1 (for Smyly, a one-run, three-inning start; for Miley, a two-inning relief appearance), the pair expressed their desire to return.

“I hope so,” Smyly said. “It’s up in the air. It’s what the Cubs want to do. I hope they see me in their plans. I would love to come back. Like I’ve said all season, just playing games here and putting on this uniform is really special.”

Said Miley about wanting to be a Cub in 2023: “Yeah, for sure. This place has been amazing.”

But are the Cubs leaning toward bringing either or both back? That’s not yet clear.

“With both guys,” Hoyer said, “in the right setup, I think we’d love to have them back.”

“The right setup” could mean a lot of things, but to begin, a reunion with the two would probably involve different contracts than the ones they had going into the 2022 season.

Miley pitched just nine times while dealing with injuries all year, and he’ll turn 36 in November. It would be a surprise if the Cubs offered him a deal anywhere close to the what they paid him this past season. Meanwhile, Smyly pitched well throughout the year (3.47 ERA, 1.19 WHIP) and had an August that showed he can still be dependable (30 innings, a 0.90 ERA and a 0.93 WHIP over five starts), but he also missed over a month dealing with injuries and he’ll turn 34 next June. A reunion with Smyly is certainly realistic, but it would likely come on a new deal.

So, at the right price, either of them would be candidates to return to the Cubs. But at the same time, it may come down to roster openings.

It seems that between the two, Smyly may be a better fit for 2023. Early in the season, when most starters were still building up following the shortened spring training, Smyly gave the Cubs at least 4 1/3 innings in each of his first eight starts. He probably would’ve made it nine had he not suffered a right oblique strain that ended his May 30 start after three scoreless innings and kept him on the shelf until July 10. Smyly had a rough July upon his return, posting a 6.06 ERA in four starts that month, but his August was so impressive that there’s a belief he could play a serviceable role next year.

“I think he wishes he could’ve thrown more innings throughout the whole season,” Hoyer said, “but the time he really got things going, he was really good.”

If the Cubs have the type of offseason they envision, that role for Smyly may at best be as their fifth starter. But he showed in 2022 that that would be far from a worst-case scenario.

“I feel good about the season I had, and I know I can help this team win in the future,” Smyly said. “We’ll see, but it doesn’t matter what I think. It’s up to them.”

Working in Miley’s favor is how quickly he helped build a strong culture within the club. As he dealt with his injuries for a majority of the year, he remained with the team rather than leave to go about his rehab elsewhere. Miley is known for bringing a positive, veteran presence to a clubhouse, and by sticking around for the entirety of the season, he brought that to a team still transitioning into its new era.

“So many guys, especially guys new to a team, would’ve probably left,” Hoyer said. “They probably would’ve found themselves home or in Arizona, rehabbing elsewhere, having no impact on a team. Just the way he is as a person, I think he felt, like, ‘I have to try to earn my money somehow.’

“And the impact he had on our young guys and our culture was awesome. He’s just a really fun guy to have around every day, but also really intentional about team building, really intentional about working with the young guys on how they can get better.

“I wish I had seen him pitch more, for sure. I think he wishes he pitched more, but I couldn’t leave the year with a higher impression of a person as far as just his desire to impact us.”

Still, the most important thing Miley could’ve done in 2022 was prove he could still provide quality innings like he’d done throughout his career, but because his various ailments forced him to miss a majority of the season, he never truly got the chance to do that.

There is a scenario in which the Cubs bring him back to serve as a long-relief lefty with the ability to make spot starts. But he’s only come out of the bullpen seven times in his 12-year career, and he may want another crack at being in a rotation — which appears unlikely to happen again with the Cubs.

“Obviously, I understand how the business of baseball works and everything,” Miley said. “I gotta go prove that I’m healthy, have a normal offseason and prove to teams that I can take the ball 25-30 times a year. That’s the challenge and the hard part, but I’m definitely looking forward to it and seeing what happens.”

Time will tell whether either of them will be Cubs again come next season, but as the Cubs look to build a pitching staff with enough depth to combat the injury bug should it bite again, both Smyly and Miley would be intriguing options.

“I think they both had a really positive impact on the organization,” Hoyer said. “There’s no finish line when it comes to adding guys that can make starts in the big leagues and that can add to your culture.”

Author

Chicago Cubs beat reporter and podcaster for CHGO. I've previously covered MLB for MLB.com and a bunch of other sports for a bunch of other outlets. Follow me on Twitter @ryan_a_herrera

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