Jake Arrieta, who turns 31 next month, will make a bit under $16 million dollars in 2017, his final season under team control with the Chicago Cubs. It’s enough money, together with his previous career earnings, that incremental differences in Arrieta’s next contract are probably not going to make the singular difference between a happy post-playing-days life and an unhappy one.

But the reality is that baseball players have a whole lot more tugging at them when it comes to their contracts than the obvious quality-of-life implications.

For one example, when it comes to players at the top of the market, seeking and landing a significant contract in free agency can have dramatic future implications for fellow players union members – it was a refrain we heard often as Jeff Samardzija approached free agency and the Cubs were unable to come to terms with him on an extension.

In a great read at ESPN today, Jesse Rogers discusses the future of the Cubs-Arrieta relationship, and it includes some thoughts from Arrieta and Anthony Rizzo on precisely that point. Rizzo points out that players do try to “set the bar” for other players down the road when securing their own contracts. Arrieta, noting that he wasn’t talking about himself, asked rhetorically, “Why would a guy take any less when he’s six months from free agency?”

Strictly speaking, the reason a player might consider doing it – as Stephen Strasburg did just last year before an arm injury limited him to just 20.0 innings pitched after July – is because a lot can happen to a pitcher’s arm in those intervening six months. Time and again, we’ve seen projected contracts for an impending free agent crumble in the final year before free agency, whether because of injury, deteriorated performance, or both.

… but we’ve also seen players perform exceedingly well in a walk year, and there’s no arguing that, if Arrieta goes out and pitches like he did in 2015, then he’s going to be in line for a Zack-Greinke-like $200 million contract in free agency.

Such a contract would not only have an obvious and significant impact on the many generations of Arrietas to follow, but also the many future MLB starting pitchers to follow. If a player like Arrieta takes his union participation seriously, then of course that’s going to at least factor into his decision on whether to accept an extension at this point, or roll the dice and head for free agency.

So the question is not so much why would Arrieta accept less than free agent-level dollars right now, but it’s instead a question of how much he’s willing to bet on himself to see what he can do this year.

And you know Arrieta. He’s not lacking for confidence.

“Somebody will pay,” Arrieta told Rogers. “That’s a known fact. I’m healthy, in the prime of my career; I’m going to be good for a long time. Whether it’s here or somewhere else, it remains to be seen.”

The sides have each said that they’re open to talking about an extension, but few pundits would tell you a deal is likely.

For the Cubs’ part, they’re up against a number of factors: they are generating significant revenue, and they will have a need for starting pitching after 2017. They are also facing a rising crop of positional talent, whose salaries will begin to escalate in tandem very soon. The new CBA rules make it very unattractive for an organization like the Cubs to go over the luxury tax limit, and a monster contract for a pitcher like Arrieta – paired with those other rising salaries – could quickly become rather restrictive.

If the Cubs were able to convince Arrieta to take a little less than he might net in free agency in exchange for right-now security? That would make plenty of sense for the team. But, as discussed, that might not make sense for Arrieta. He’s been a fantastic pitcher for the Cubs, and, although I’m not saying it’s time to close any doors, I do think all sides have made it fairly plain that the most likely scenario here is that Arrieta bets on himself, pitches to the best of his ability in 2017, and then sees what free agency has in store.


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