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5 Offseason Moves For The Cubs: 1. Starting Pitching

Updated: Dec 3, 2019

The way the last two seasons ended for the Cubs left a pretty sour taste in their fans’ mouths. From blowing a division lead in 2018 and losing in the Wild card game to missing the playoffs completely in 2019, the Cubs are officially open for change.

Theo and the front office are finally willing to part ways with some of the loyal companions that brought them the World Series in 2016. I fully expect the Cubs to make some pretty impactful moves this offseason and there is no time to wait for them. They should be going full steam ahead.

There are 5 key ingredients to a perfect offseason for the Cubs and it starts with signing a big-time starting pitcher in Free Agency. A lot of people think the Cubs are strapped for cash heading into this offseason but I disagree. They had a lot of bad contracts come off the books which clear up money for them, as well as the launch of their new network, Marquee Sports, which is set to open in February 2020. As a result of all this, the Cubs will be bringing in cash and have trimmed some of the fat from those old contracts. (A few of those include: Cole Hamels $20 mil., Steve Cishek $6.5 mil., Ben Zobrist $12.5 mil. ... Right there is $39 mil.)

Signing a big-time starting pitcher in Free Agency

Say what you will about Yu Darvish but his second half of the year was remarkable (4-4, 2.76 ERA, 118 K, 7 BB, .199 opp BA, and 13 K/9). As fans, all we can do is hope that continues into next season. If it does, all the negativity surrounding Theo and the signing will be resolved.

But he’s still not enough. Thinking back to 2016, the Cubs’ rotation was dominant. Both Arrieta and Lester finished in the top three for Cy Young voting and in order to win another World Series, they need to (or at least try to) get back to that same type of dominance. The only way to do that is by signing a sure-fire ace for the next 6-7 years. With questions surrounding Darvish, you can’t say for sure if he will be that guy moving forward. But this free-agent class is loaded with premier arms for the team to choose from.

It’s unlikely the Cubs will go after Gerrit Cole, but I could see them making a play at Stephen Strasburg and here’s why. If they go out and get their ace (Strasburg) this season, they now jump to having (one of, if not) the best rotation in baseball. The Cubs have had a bad bullpen for a while, but as we learned with the Nationals, you don’t need to have a high-end bullpen if your starters can rack up innings.

We all know Lester isn’t the workhorse he once was, but that’s the price you pay when you sign a 31-year-old pitcher to a long term contract, you bite the bullet on his last two-three years. You hope you’re going to get your moneys-worth in the beginning and fight the uphill battle towards the end. (That is nothing against Lester he has been the best signing in franchise history and invaluable to the Cubs in a lot of ways, simply the truth)

If the front office is willing to bite the bullet for a couple years, go after a big name, and pay a lot of money for starting pitching, this would not only solidify their rotation WELL after the Lester-era, it would send a message to the league, and to the fans, that the Cubs are once again contenders and not pretenders.

What better way to help David Ross (a former catcher no less!) transition into his new role as manager than to have a top 5 pitcher in the sport at the front of his staff.

I’m a firm believer that if you’re going to spend money you invest it in your rotation. It’s easier to produce year-over-year as a pitcher than it as a hitter.

Signing Strasburg is a great fit, but a long-shot. However, the Cubs still need rotation help. Other solid options include: Madison Bumgarner, Hyun-Jin Ryu, Michael Pineda

If the Cubs decide to ride it out and wait to sign a pitcher post-Lester, here are some free agents in 2020: Trevor Bauer, Robbie Ray, James Paxton, Marcus Stroman. 2021: Noah Syndergaard, Chris Archer, Mike Foltynewicz.

The time is now for the Cubs to get their next great starting pitcher.


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