Chicago Cubs Rumors: Could Jake Arrieta sign an extension?

After last season’s Cy Young, it looked unlikely the Chicago Cubs could sign Jake Arrieta to an extension after his 2017 season. But it appears his agent, Scott Boras, is willing to negotiate with the Cubs in January.

There was a time when Scott Boras used to rip the Chicago Cubs. They weren’t spending enough, he said. Back then, that may have been partially true. But the Cubs had a plan, and they were sticking to it. Regardless of what Boras had to say. Now it appears he’s changed his tune. The Cubs and Jake Arrieta will get together in January to talk about a possible extension. This, especially for Boras and one of his clients, isn’t the norm.

The tendency with Boras is to wait until the client hits free agency. It’s not completely out of the norm. Last season he negotiated a $175MM deal for Stephen Strasburg. So why the change of heart from Boras? Is there something he knows that we don’t”

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Not really. What it comes down to are a few simple things. First, the Cubs have money. The same team Boras ripped publicly in 2013 for not spending is doing just that. Now, Boras isn’t every going to admit he was wrong or to give a “discount” to a team. But he very well may realize the Cubs have the money to spend and would like to keep Arrieta a Cub for the near future. A five-year deal would take him into his age 35 season.

Reason to believe it could happen

There’s ample reason for Boras and Arrieta to believe he’ll get a deal similar to, but not the same as Strasburg. Clayton Kershaw, Cole Hamels and Homer Bailey all received nine-figure deals after having five years plus of MLB service time. And while Arrieta might not reach that level that he did in 2015, he’s more than capable of flashing that ability over the course of a season. A look at this year’s free agent pool makes us realize why it might not be a bad idea to sign Arrieta to an extension.

The Cubs have big contracts with Jon Lester and Jason Heyward already. But it’s not as much about what they’re paying these guys as what their revenue will bring in. The Cubs are champions. They’re drawing sellout crowds. And the video boards and a possible TV deal in the future will only bring in more cash to the Cubs. I mean, Rich Hill will get $18 million per year with his new deal.  I like Hill and his comeback story, but Arrieta is going to get paid more than that. Without question.

Next: Cubs sign Uehara to one-year deal

It’s tough to say if the Cubs will meet Boras on his demands for Jake. Yes, Jake isn’t a kid anymore. But I’d say he’s as fit and healthy as one with his ridiculous fitness regime. He peaked later in his career and may continue this run for several more years. Even if the two sides can’t come to an agreement in January, it won’t be the end of the conversation. It’s simply a waiting game to see what the Cubs decide to do.