Chicago Cubs

Chicago Cubs: The ever-turning wheels of the starting rotation

Updated Mar. 4, 2020 11:20 p.m. ET

Fansided, Nicholas D. Blazek/FanSided via Cubbies Crib

The Chicago Cubs have built this roster with youth and versatility in the field and at the plate. Pitching has been a market they have looked at with numbers over talent. This season will be an interesting one for the Cubs rotation–whoever happens to be part of it.

The Chicago Cubs starting rotation beyond this season remains a mystery. Jon Lester and Kyle Hendricks are locked in beyond 2017. Jake Arrieta is in his final year of his contract. John Lackey is in the same, and this could be the final year for the veteran righty. The final spot has been the talk of most Cubs fans. The unexpected addition of Tyson Ross to the free agent market added to the intrigue. But where is this rotation headed beyond this season?

The discussions between Arrieta and his agent Scott Boras and the Cubs will continue after the first of the year. What once seemed unlikely may be within reach for the Cubs. After Arrieta’s ascension to the 2015 NL Cy Young, it looked like a massive payday would be in line for Jake. And while 2016 wasn’t as good, it was still a strong performance for Arrieta. Boras loves to play hardball at times, but he would be fine seeing his client locked up long-term with the Cubs, as opposed to seeing what the market would yield.

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The growth of Hendricks continues to be feel good story for the Cubs. Lacking the electric fastball that most prospects have, Hendricks harkens back to the days of Greg Maddux–using control and location to keep hitters off-balance. Watching him throw a fastball in the mid to high 80’s and good hitters swing and miss? We’re not calling him the next Maddux, but it’s hard not to get excited about him. And with his earliest free agency date in 2021, that’s four more year’s or potential growth for “the professor”.

Lester is the unquestioned ace of the staff

Lester is anchored in as the ace of the staff, and for good reason. Some questioned the deal he was given last season, but no longer is that the case. His inability to throw to first base will still be a question. With David Ross retired, can Willson Contreras slide in as his personal catcher? The arm strength is without a doubt there for Contreras. But can he provide the comfortability and confidence for Lester behind the plate? 2017 will be a test for Lester as he will be without Ross for the first time in several years.

Lackey came to Chicago to get another ring, and he did exactly that. So will 2017 be his swan song, or does he have more in the tank? Lackey is a true grit competitor. He’s from the “old school” of the game. Nothing from his repertoire will surprise you, but he’s still been successful in his career. Lackey has said he wouldn’t be against playing beyond this season if the ability and desire is still there. Even then, would that be with the Cubs or somewhere else?

Pitching depth improving but not yet ready

The most intriguing bit is the final spot in the rotation. The Cubs have some talented prospects (Dylan Cease, Duane Underwood), but neither has pitched beyond Double-A. So “plan A” is to move Mike Montgomery into the rotation. It’s something he’s familiar with as the Cubs and Mariners both used him in spot starts in his career.

Plan B? Ross is high on the Cubs radar–as well as every other team in baseball. But if Theo Epstein and Jed Hoyer believe he will make this a better team, they’ll do all they can to bring him to Chicago. The rest of the pitching free agent market is less than stellar or have already been signed. So the likelihood of the Cubs doing something eye-popping is unlikely.

The Cubs made the decision to focus on position talent in the draft while using the bulk of late picks to stock up on pitching talent. The thought being that top talent guys can get hurt, so use the later rounds to build the depth. It may take longer as some of the arms haven’t progressed as much, but it seems to be working out–at least on the surface of the Cubs prospect rankings.

This coming season will be a pivotal one for the Cubs as the wheels of the rotation will once again be turning. Will they find an answer with one of their prospects? Or will they bite the bullet and sign Arrieta to an extension?