Chicago Cubs: Fifth starter options abound heading into offseason

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Four of the five starting rotation spots appear to be under lock. But the Chicago Cubs have a critical decision to make regarding that fifth and final berth.

Let’s just start with the elephant in the room – the Chicago Cubs seemingly botched signing of right-hander Tyler Chatwood. Last offseason, Theo Epstein kicked off the winter by signing the former Colorado Rockies right-hander to a three-year, $39 million deal.

He led all of Major League Baseball in base-on-balls, pitched to a 5.30 ERA, 1.804 WHIP and .089 strikeout-to-walk ratio in 103 2/3 innings. That’s right – he walked more guys than he struck out. Late in the season, Chicago went away from Chatwood and the guy barely saw the mound in the final month.

Can the Cubs afford to go into next season with Chatwood penciled in the starting rotation? Remember, he still has two years and $25.5 million left on that deal.

Chicago managed to keep Chatwood on the 25-man roster until the Sept. 1 roster expansion. After that, they were able to hide him deep at the end of the bullpen. The hope, at least for the Cubs, is that Chatwood can work with Jim Hickey this offseason to get himself right.

However, as Cubs fans have learned the last two seasons of Jason Heyward working on his swing taught us that offseason improvements don’t mean anything until we see it working in the regular season. So, it will be difficult to have any confidence in Chatwood until he consistently pitches well.

I don’t think the Cubs can count on Chatwood next season. I don’t even think the Cubs should allow him to hold a 25-man roster spot hostage the way Edwin Jackson did in 2015. The money will be difficult to swallow. Maybe the front office can dump part of his contract on a team hoping to buy low on Chatwood. But I don’t think a team that is looking to compete for another World Series should begin the season by counting on someone who performed as badly as Chatwood did this year.

(Photo by Gregory Shamus/Getty Images) /

Chicago Cubs: Drew Smyly ready to return from surgery

I both do and don’t understand signing Smyly last offseason. I know he was coming back from Tommy John surgery and wasn’t going to pitch much, if at all, for the Cubs in 2018. What I don’t understand is why the front office would then be comfortable turning around and handing him a spot in the rotation in 2019 after he didn’t pitch last year.

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Just like Chatwood, Smyly signed a multi-year deal last winter. There is still one year and $7 million left on that contract. If he doesn’t work out as a starter, Smyly could turn into a valuable left-hander in the bullpen.

If the last spot in the rotation comes down to Smyly or Mike Montgomery, that situation will seem a lot like the 2017 situation. That year the Cubs chose between Montgomery and Brett Anderson, another left-hander, for the last spot in the rotation. Anderson lasted only six starts that season before going on the disabled list and eventually being released.

But even if Anderson had worked out, the front office would have been faced with a pitcher that the Cubs took a risk on, he then re-establishes his value before hitting free agency. That’s the best case scenario with Smyly except this time, more up front money is on the line.

Chicago Cubs: Mike Montgomery looking to build on 2018

Montgomery pitched well enough as a starter the last couple of seasons to warrant a starting job in the Majors. But, as a Cub, I think he is too valuable for Chicago to begin the season with him in the rotation. As the last two seasons have shown, the Cubs need starting pitching depth.

There are a lot of factors at play here. Yu Darvish is coming off an injury plagued first season on the North Side. Jon Lester enters 2019 another year older. So, in all honesty, whoever grabs that fifth starting spot becomes critical. Even the ‘young’ starters, Jose Quintana and Kyle Hendricks, could wind up hurt.

With this in mind, Mike Montgomery isn’t most valuable as your fifth starter. Rather, he should slide into the same role he began last year in – a sixth starter and swing man. An insurance policy, if you will.

In 2022, Montgomery is eligible to become a free agent. If the Cubs keep holding him back from being a full-time starting pitcher, he may very well choose to leave. But until then or until a better sixth starter presents himself, I suspect Chicago will keep Montgomery right where he’s at.

Chicago Cubs: Cole Hamels everything Cubs needed and then some

The Cubs hold a one-year, $20 million team option on Cole Hamels. Is that too expensive? If Chicago chooses not to pick up his option, he has a $6 million buyout in his deal the Rangers will pay as part of the agreement from the trade that brought him to the Cubs. But if the left-hander becomes a free agent, he will probably seek a multi-year deal.

Next season, Hamels will be in his age-35 season. Would Chicago commit multiple years to a pitcher already in his mid-30s? I doubt it. Picking up an option makes more sense, but, then again, you’re committing a good chunk of payroll to Hamels with other needs on the roster.

Re-signing Hamels would also make three-fifths of the rotation left-handed. Smyly and Montgomery makes two other starting pitchers under contract for next year who are also left-handed. That might be too many lefties, depending on who you ask.

Chicago Cubs: Spot starters abound in the Minors

Adbert Alzolay, Jen-Ho Tseng, Duane Underwood Jr. and Alec Mills are all in the Cubs minor league system. They are all also on the 40-man roster already. Are any of them ready to be the fifth starter in the Cubs major league rotation? Sadly, the answer appears to be ‘no’.

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Alzolay came into 2018 season as the most promising starting pitching prospect in the Cubs system. Unfortunately he missed a large portion of this season with an injury. He probably needs more seasoning.

Tseng has twice been the Cubs’ Minor League Pitcher of the Year. He has made two starts in the Majors – one coming in late 2017 and another early this season. Both were disasters. Tseng’s 2018 minor league season didn’t go much better.

He pitched to a 6.27 ERA with Triple-A Iowa this year, making 26 starts. The right-hander might be reaching the point where it is difficult to justify keeping him on the 40-man roster.

Duane Underwood Jr. made one emergency start for the Cubs in 2018 and it was a modest success. But that start also showed that Underwood probably isn’t ready yet. Underwood didn’t even get called up in September when rosters expanded.

Alec Mills showed that he is decent starting pitching depth. If the Cubs can continue to stash him in the minors, I expect that will be his role. He might be 2019’s Luke Farrell.

Chicago Cubs: Is Theo ready to pound on free agents and the trade market?

In case you haven’t heard yet, this year’s free agent class is one of the most talented in recent memory. The headliners are position players but there are a lot of starting pitchers who will be or potentially could be free agents too.

Dallas Keuchel, Gio Gonzalez and Nathan Eovaldi are all free agents. Since Gonzalez and Eovaldi were traded this season they won’t have draft pick compensation attached. That’s obviously huge for a team like the Cubs looking to reload their prospect pool while remaining competitive.

Clayton Kershaw and David Price can opt out of their contracts and become free agents. Kershaw may opt out and then just sign a bigger contract with the Dodgers. It might be risky for Price to opt out after yet more postseason woes.

Chris Sale and Madison Bumgarner both have team options for next season. I doubt either one of them become free agents. However, their recent injuries do at least make it a slight possibility. But if that is the reason they become free agents, do the Cubs want to take a chance on another pitcher with a history of recent injuries?

There’s also the possibility of the Cubs trading for a starting pitcher. In 2017 the front office was finally able to trade for a young cost-controlled starting pitcher in Quintana. I don’t know if they will be able to do again. But if Epstein is serious about trading from the Major League roster, it’s possible.

Sale, Quintana, Gerrit Cole, Sonny Gray and Chris Archer have all been traded in the last couple of years. Other than the Mets’ pair of Jacob deGromm and Noah Syndergaard, I’m not sure who the Cubs would want to target.

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No matter who ends up joining the Cubs rotation its looking like its going to be a very expensive spot. The Cubs have already invested in Chatwood, Smyly and Montgomery’s contracts in that spot and may well invest another $20 million in Hamels’ option or a free agent.

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