Barring a spring training signing of maybe Jordan Montgomery, the Chicago Cubs have a group of four pitchers that will be competing for the fifth starter job and I’m here to rank them from most likely to win the spot to least likely.

All four pitchers spent time in the starting rotation at one point or another in 2023: Drew Smyly, Javier Assad, Hayden Wesneski and Jordan Wicks. So, is there a front runner for that fifth starter job?

Well, there are a bunch of things to consider besides last year’s performance because if you did that, then you probably think it should be Assad. However, players do in fact make changes in the offseason and I guess we’ll see during spring training if those adjustments are real. And well, sometimes as fans we don’t really get a clear idea of that going off results because the team may be focusing on specific things down in Arizona rather than how many runs a pitcher gave up in their outing.

You also have to factor in the longterm plans a team may have for their younger pitchers, coupled with which guys have minor league options and which don’t. While I’d prefer to go with one of the young guys to round out the starting rotation, I ultimately believe it’s going to be the veteran lefty to get the first crack to prove himself again.

Drew Smyly

Have I tried trading Drew Smyly to the Boston Red Sox for Kenley Jansen this offseason? Maybe. But hey, Jansen is kinda hurt now and Smyly isn’t going anywhere. More importantly for this conversation, the 34-year-old lefty can’t be sent to the minor leagues.

Smyly was pretty damn good to begin the 2023 season and then he was really damn bad, eventually leading to his demotion to the bullpen. And hey, Smyly was actually good as a reliever down the stretch. As a pitcher who has one guaranteed year left on his contract, you know Smyly would obviously prefer to be a starter in 2024 to better position himself for a richer deal next offseason.

Credit to Smyly, who worked with Driveline Baseball this offseason and has now added a couple new pitches to his repertoire.

Via the Chicago Tribune.

Eventually, Smyly and the personnel at Driveline worked on pitch design for his repertoire. Most notably, Smyly has added a splitter and slider to his pitch mix. Live batting practice and eventually games will be important indicators of the effectiveness of his splitter. He’s already thrown four live BPs, including three at Driveline.

The splitter became an attractive option after Smyly felt sometimes limited to a fastball-curveball combination, which makes it hard to get through a lineup multiple times. The curveball will always be Smyly’s go-to pitch, but the splitter presents another option to generate whiffs. Driveline personnel were really excited about his splitters metrics, Smyly said, and that it could grade out as one of his best pitches.

Working with Driveline doesn’t automatically guarantee positive results, but there’s a reason more pros are going there year after year.

Drew Smyly looking great in a recent pitch design session with @langintots13 🔥 pic.twitter.com/nq7o52gne3
— Driveline Baseball (@DrivelineBB) December 16, 2023

A new splitter and slider may be the key for Smyly to once again establish himself as a competent starting pitcher in 2024. And the thing is, as bad as it got for Smyly in the second half of last year, he does have some sustained success with the Cubs. He came back from a lat injury in 2022 and through June 19, 2023, Smyly made 28 starts and recorded a 3.32 ERA with a 1.19 WHIP in 146.1 IP.

I don’t think new Cubs manager Craig Counsell is going to default to the veterans, but if Smyly’s new arsenal is working, then the team probably thinks they can get the most out of Smyly as the fifth starter to begin the season.

Javier Assad

Javier Assad is the man. Need him to throw three innings out of the bullpen because the starter got blown up early? Assad will go out there and shut down the opposition. Need him to make a spot start because of an injury? Assad will step in on short notice. Need him to join the rotation because of a longterm injury or poor performance? Assad won’t only fill in, he’ll be one of your better starting pitchers when you need it the most.

From Aug. 5-Sept. 19, Javier Assad made 9 starts and posted a 2.84 ERA in 50.2 IP. He allowed more than 3 ER one time, while pitching 5+ innings 7 times.
— Aldo Soto (@AldoSoto21) September 29, 2023

I still have no idea why David Ross decided to put Marcus Stroman back in the rotation in late September last year, when it was obvious Stroman didn’t have it after a short ramp up following his injured list stint. Yet, it’s a reminder that Assad was fantastic when asked to step in during the summer.

However, Assad’s flexibility may ultimately hurt his chances of winning the fifth starter job because the team is well aware that he has the capacity to go back and forth from the bullpen to the rotation at the drop of a dime. So, I have Assad as the runner-up, with him beginning the year in the bullpen.

Jordan Wicks, Hayden Wesneski

If either Jordan Wicks or Hayden Wesneski don’t win the fifth starter job, I want both to begin the season at Triple-A, where they continue to start. I hated how Wesneski kept getting yo-yoed from starter to reliever back to starter back to reliever in 2023. Give Wesneski a normal routine in the starting rotation, so that in case of injury he can actually step in and provide length in his appearances.

I’ve been a believer in Wicks and do think he will eventually be counted on by the Cubs. But like Wesneski, I don’t want the Cubs stunting his development as a starting pitcher by having him be a reliever. Keep him ready in Triple-A and if needed, give Wicks that chance to re-join the MLB rotation.

I’m putting both Wicks and Wesneski at the bottom of the competition both because I think it would be better for them longterm and secondly, they have minor league options.