jake arrieta vintage

As you may well know, Jake Arrieta will be a free agent at the end of the 2017 season. What that means is that the Cubs are only guaranteed to have him under control for the next 1.5 seasons before he’s allowed to choose from any team in baseball.

Although Arrieta has consistently indicated that he’d like to stay in Chicago, he has added that there are two sides to every negotiation (as there are sides to stories), and that he’s perfectly willing to test out the market should it come to that.

The Cubs have explored extending Arrieta in the past, although their efforts have reportedly been in the 3-4 year range, while Arrieta’s camp has been looking for something closer to a 6-7 year deal.

Despite the obvious interest in an extension from both parties, many believe that Arrieta is destined for free agency, in no small part because he’s represented by agent Scott Boras, who has notoriously steered clients away from extensions in the past. But that narrative got a pretty significant update this week when Stephen Strasburg, a Boras client just five months away from free agency, signed an extension with the Washington Nationals.



Until that deal was inked, the most compelling and similar case in recent memory for Arrieta’s situation, of course, was Max Scherzer – another Boras client, and a former Cy Young Award winner, who turned down a big extension from the Tigers a season before free agency. Scherzer bet on himself, and received a much larger deal later from the Nationals. However, Scherzer is no longer the only proxy for Arrieta, because now we’ve got the Strasburg data point (another top of the rotation starting pitcher who’s represented by Scott Boras).

Extensions this close to free agency are extremely rare (most guys prefer to bet on themselves at that point) and ones for Boras’ clients are almost unheard of. Needless to say, this was quite a shocking revelation. So, then, with new information in hand, let’s take a look at both Boras’ clients (Scherzer and Strasburg), to consider the differences and similarities to Jake Arrieta, before seeing if we can deduce anything in regards to an extensions with the Chicago Cubs.

First up, Max Scherzer, who is fresh off of a record-tying 20 strikeout performance.

In the offseason before Scherzer became a free agent, the Tigers offered a fairly substantial 6 year/$144 million extension … which Scherzer shockingly turned down. At the time, many suggested that it was a mistake and that Scherzer was likely to pay the price. Many, but not Scott Boras. Sure enough, less than 12 months later, Scherzer signed a huge $210 million deal with the Washington Nationals (albeit with some deferred money), and became one of the top paid starting pitchers in baseball history.

So, is Jake Arrieta destined for the same fate?



Both Patrick Mooney (CSN Chicago) and Gordon Wittenmyer (Chicago Sun Times) can see the similarities and wrote about them recently. Although Scherzer was fair bit younger at the start of his contract with the Nationals (30) than Arrieta will be in his first year of free agency (32), neither had racked up a lot of mileage on their arm. Scherzer had thrown 1,240 big league innings by Opening Day 2015 and Jake Arrieta projects to be right around 1,200 by Opening Day 2018. By contrast, Jon Lester, 31 at the time, had thrown just about 1,600 innings by Opening Day 2015, and he signed a 6 year/$155 million contract in December of 2014.

But that was two years ago and his contract is looking mighty attractive right now. In fact, that deal would likely be turned down by Arrieta at this point, given the upward trend in the market over the past few years and cost of elite starting pitching in free agency. But that doesn’t mean Arrieta is destined for $200+ million deal, either.

Which brings us to Stephen Strasburg.

Earlier this week, most of the baseball world was relatively shocked when word broke that Stephen Strasburg had signed an extension with the Washington Nationals. Although Strasburg has dealt with some serious injury questions in the past, he was set to be just 28 years old when he hit free agency this winter (a class that is mostly void of much significant talent). In other words, if Strasburg forwent free agency for an extension, you knew it had to be for a lot.

And, well, it was.

At age 27, Stephen Strasburg signed a 7 year/$175 million deal with the Nationals that will keep him in Washington through the 2023 season (unless he opts out after years three or four). Now, to be quite clear, the Nationals once again deferred A LOT of money in this one (like they did with Max Scherzer, not coincidentally). According to Cot’s Contracts, $70M was deferred without interest ($30M in 2019, $10M in 2020, $30M in 2023) which reduces the contract’s present-day value to roughly $162M. Still, it was healthy extension for a talented pitcher who hasn’t always been healthy.

First, let’s discuss the positive angle here. We now have definitive proof that, if the price is right (and this is a fairly reasonable deal for both sides), Scott Boras is willing to help his ace-level clients sign extensions and stay in the city they prefer. Boras has claimed as much in the past, but for the most part, it seemed like he was just playing the part.



On the other hand, you can argue that Strasburg isn’t that good of a comparison for Jake Arrieta. For one thing, Strasburg is just 28 years old, which allowed the Nationals to be far more confident with their lengthy and costly extension than they might be with Jake Arrieta at 32 years old. Furthermore, despite Strasburg’s injuries, he’s been worth more through his age 27 season than Jake Arrieta has been in his career. Put simply, Strasburg is younger and has been good for longer. Does it really make sense for Arrieta to receive the same extension at 32 years old that a 28 year old just received?

I’ll bet one side thinks so. And it’s the side that would point out that, since Arrieta reinvented himself with the Cubs, comparing his numbers to Strasburg’s would not be much of a comparison. Arrieta’s been in a class all his own.

I have no doubt that the Cubs will once again try to extend Arrieta this coming offseason, but they’re going to try to do so on their own terms. “You pay attention to everything that goes on in the game, but [the Strasburg extension] doesn’t impact us too much,” Epstein said via Patrick Mooney at CSN Chicago. “Obviously, it will impact markets and we have to operate in markets. But it is what it is.” Epstein went on to add that the Cubs have done well at putting together pitching staffs in the past, and they’ll have to continue to do so whatever happens with Arrieta.

Again, I suspect the Cubs will try to extend Arrieta once again in the offseason, but for now, there is nothing new to report. If Arrieta has another great 2016 season (he’s well on his way), he’ll be just one season out from an absolutely enormous contract. Given his well-known and well-earned self-confidence, and intense health and fitness practices, I wouldn’t bet against him to bet on himself, regardless of his agent or any other pitchers in the market.




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