What Should Cubs Offer When They Talk Extension During Jake Arrieta’s Arb Discussions?

If it seems as though we’ve been talking about Jake Arrieta‘s future with the Cubs for a while now, it’s because we have. But now that he’s heading into his final year of club control, the conversation is tinged with a bit more urgency than in the past. Arrieta and the members of the front office weren’t compelled to tie anything up last offseason, what with each party understanding the position of the other and neither wanting to sacrifice leverage.

Coming off of a season in which he posted the best second half on record en route to a Cy Young, it appeared as though all of that leverage was in Arrieta’s favor a year ago. Then you look at Johnny Cueto‘s six-year, $130M guarantee with the Giants and the $206.5M the D-backs handed Zack Greinke over the same period and you see why the open market would be appealing to Arrieta. Oh, there’s also the small matter of Scott Boras serving as the Cubs pitcher’s representative in contract negotiations. So, yeah, he ain’t comin’ cheap.

According to ESPN’s Jesse Rogers, Boras has said an extension will be discussed when the sides meet in January to work out Arrieta’s arbitration raise. Such talk has previously been limited to the offseason, but Rogers also posits that Arrieta “seems like the type” to carry negotiations into the regular season should it come to that. For what it’s worth, it doesn’t sound like Boras is a big fan of that tactic in this case.

Either way, it makes sense for the Cubs to try to work something out now, when the pendulum has swung back in their favor a bit. Not that the market for elite pitching is anything short of insanely pricey, just that the team may have recouped a nice chunk of leverage after last season. I mean, yeah, Arrieta’s season was bookended by that early no-hitter and two World Series wins, but he was not the same dominant pitcher at whom we marveled in 2015.

So what does this mean for Arrieta and the Cubs when they sit down after the holidays to talk turkey? The first thing to be considered is his salary for 2017, which MLB Trade Rumors projects will jump from $10.7 million to nearly $17 million. That’s a bargain when compared to the market, so the Cubs are going to be getting great value even if Arrieta pitches like a mid-rotation starter next season. And that might be exactly why Boras would be willing to work on a long-term deal.

Stephen Strasburg inking a seven-year, $175M (that’s $25M AAV with opt-outs after years three and four and massively escalated figures of $38,333,333 in 2019 and $45M in final year of 2023) extension this past May really got Arrieta’s ears perked up and had him talking tough when it came to his own value. Among the sentiments he expressed when asked about the his future were that “aces get seven years” and “You want to be paid in respect to how your peers are paid.” That was before his performance flagged a bit through the second half, but it paints an accurate picture of what we can expect Arrieta’s mindset to be as he looks to parlay his talent into nine figures.

Knowing that the guy wants to get a six or seven-year commitment and that the really elite arms are getting $25-30 million AAV, you’re looking at an ask of something in the $150-210 million range. That’s for a guy who will turn 31 in March and whose inconsistent mechanics are anything but a guarantee of a return to dominance. Even though such a deal, at least the lower to middle range of it, would be very well in keeping with what the market dictates these days, I’m not sure how palatable it’ll be for the Cubs. If Arrieta and Boras believe they can get something toward the high end of that scale, I’d gladly offer $18 million in arbitration and wish them luck in free agency next season.

At that point, you’re talking about a guy who will be 38 or 39 by the time the contract winds down. Who knows what will happen to his health and velocity between now and then, or whether his mechanics will allow him to maintain enough control to remain in the upper echelon of starting pitches for even the first few seasons of the pact. Risk and uncertainty are inherent risks in any big contract, though, and you can’t discount the notion that some team may be desperate enough to throw a boatload of cash at a 32-year-old Cy Young winner.

What about this though: The Cubs could offer Arrieta a five-year, $125 million deal with opt-outs after years two and three and vesting options for $20-25M in the sixth and seventh years that would kick in after 200 innings pitched or some such. Then add Cy Young and All-Star bonuses, a couple million here or there. This would buy Arrieta out of his final arb year, paying him about 50% than he’d have earned otherwise, and provide security through at least his age-35 season. And as we just saw with Rich Hill, it’s still possible to score a decent payday in your late 30’s.

I can’t imagine such a deal being labeled ersatz baseball or drawing accusations that the Cubs had committed the apogee of wrongs, though I’m not sure it’s quite enough to convince Arrieta to forego a shot at free agency. If he and/or Boras believes there’s a team that will guarantee seven years or that will go to $30 million AAV, there’s every reason to go out and try to find it. But, and here’s where reality and self-awareness start playing a big role, what happens to that monster deal should injury or poor performance mar Arrieta’s 2017 campaign?

Not that I want or am predicting those things, just that they should enter the conversation when weighing the pros and cons of working out a contract extension. It’s the smaller lump-sum payout on the lottery winnings, the bird in hand, choosing to stand on 13 when you see a 6 for the dealer. But that’s coming from a person who’s a little cautious by nature. Seeing the money handed out to guys like Greinke and Strasburg and Max Scherzer (7/$210M), it’s easy to understand why someone with as much confidence as Arrieta might not want to settle right now.

With that in mind, I’d probably be willing to bump it up to 5/$135M ($27M AAV) with the same opt-outs, incentives, and vesting options (which could maybe get closer to $25-30M). Like an IOU from Lloyd Christmas, those clauses are as good as real money. Outperform, go free and get more. Underperform, you still get fat paid. Sounds like a good deal to me, one that that satisfies Arrieta’s desire to be paid like an ace while also appealing to his hubris.

A quick note here that this extension figures are up from what I had suggested last year, which might seem kind of strange all things considered. Seeing how other contracts shook out, not to mention this year’s results and the recent increase in ticket prices, I figured a bump in the offer was in order.

We haven’t even discussed the implications on payroll and we won’t here, but I’ll note briefly that John Lackey and Miguel Montero come off the books after this season. Wade Davis and a few other guys, as well. Of course, you’ve then got to factor in raises and/or extensions for the young position players and such. The luxury tax threshold will continue to rise under the new CBA, so that helps to provide a little more leeway. Even so, and this will be my last point here, there’s another reason to want to limit a guaranteed deal to five years.

The new CBA will govern Major League Baseball only through 2021, at which point things could get very contentious. While each year in the future has less influence on decisions made today, it might be wise for the Cubs to hedge their bets against the unknown of the next labor agreement. The presence of vesting options could render such foresight moot regardless, but it’s something I wanted to throw in there to provide a bit of additional context.

So where do you fall on this? Should the Cubs back the Brinks truck up for Arrieta in order to alleviate what looks at this point like a serious deficiency after next season, or should they put a reasonable offer on the table and let him walk if he thinks he can get more? If granted GM-for-the day powers, what kind of a contract would you offer him?

This is something to keep an eye on as we head toward the season and the two sides sit down across the table to discuss options. I’m sure it’ll come up more than once at the Cubs Convention, too, so stay tuned.