The Rundown: Revisiting a Kris Bryant Extension, J.D. Martinez Changes Agents, Otani Stuff

While we’ve used it as a backdrop to discuss how much the Cubs will spend in free agency or whether they’ll pursue Giancarlo Stanton, we have yet to really dig into the nitty-gritty of why they’ll need to stay well under the cap. And no, I’m not talking about Bryce Harper. Well, I am, but we’ll keep him on the back burner for now.

Actually, no, let’s discuss Harper before we get to his fellow Las Vegan. FanRag’s Jon Heyman wrote last week that “There continue to be whispers that Bryce Harper could eventually wind up with the Cubs,” which is nothing new. The Cubs are an attractive team with a wide-open window of contention and there are few better ways to make baseball fun again than to re-partner with a childhood pal.

Plus, O’Hare has plenty of nonstop flights home to Vegas (which is reportedly important to Kayla Harper, Bryce’s wife).

While it sounds far too good to be true, it’s more than plausible to think the Cubs will be monitoring Harper’s free agency. They’d be stupid not to. Which means they’ve got to have a lot of money available to put toward what is likely to be the biggest contract ever, whether in terms of AAV, total value, or both. But they also have to maintain enough room on the payroll to hand out at least one more monster contract three years later.

There’s also the matter of having to field a team around the two transcendent superstars, which means extensions for several other young players in the coming years. Be that as it may, our focus for now will remain on Bryant, who would certainly command the most from among the Cubs’ core players were he to hit the open market.

He’s also the one with whom the Cubs have had the most urgency (at least as far as what’s been reported) when it comes to extension talks, though they’ve had equally little headway with everyone else. Speaking about an extension back in May, Bryant said he was planning to “just play it out and see where things go.’’

That could mean a lot of different things, the most likely of which is that he and his agent, the sharkily shrewd Scott Boras, want to see what happens with some of the big free agents over the next couple seasons. Even more than Harper, the barometer for Bryant’s bargaining power will come from third basemen like Mike Moustakas, Josh Donaldson, and Manny Machado.

It’s important to note that Bryant isn’t necessarily opposed to an extension, just that he’s going to want a better idea of where the market is heading before he gets serious about it. But the Cubs would certainly prefer to get something locked up as soon as possible, which would serve the dual needs of locking Bryant in and giving them a clearer picture of how much they’ll have available moving forward.

This is where the matter of Bryant’s upcoming arbitration raises comes into play, as even significant raises over the next four seasons won’t come close to equaling the AAV he could get from an extension. By buying out his arb years, the Cubs could decrease the overall value of the deal relative to a free agent contract in exchange for upping Bryant’s earnings while also eliminating the annual exchange of figures.

MLB Trade Rumors has Bryant projected at $8.9 million for next season, which feels a little light to me. If we use Ryan Howard — who followed his Rookie of the Year season with an MVP campaign in 2006 — as a comp, Bryant should be in line to at least equal the phormer Phillie’s $10 million. And Howard was at $900,000 in that sophomore season, just $105K less than Bryant earned.

Factor in Bryant’s comparative youth (Howard was 28 in his third season, Bryant will be 26 in his fourth) and inflation (the game’s economics have shifted in the last 11 years), and you can you see how KB could easily pull down $12 million or more next year. It’ll only go up from there, perhaps capping out at around $20 million or so.

Heyman mentioned that the Cubs were using Mike Trout’s six-year, $144 million pact with the Angels as a jumping-off point and that they’d even prefer to push it out longer. So let’s say they were talking about something like 7/$170M, which would be $24.3 AAV. Not too shabby.

Working with a few different assumptions, I’m thinking such a deal would pay KB about $32 million — give or take a few million — more over the next four seasons than he’d earn through arb raises. And even commanding a $30 million AAV deal in free agency would only be about $17 million more than said extension in those three additional years. So Bryant is coming out ahead by about $15 million. Why, then, would be have been so reticent to sign?

I believe the answer lies as much in Bryant’s grounded personality as it does in his representation. Rather than trying to fleece the Cubs by waiting as long as possible, this is largely a matter of Bryant being perfectly content with where he’s at right now and not being in any hurry to get the megabucks that are coming his way eventually. Boras is definitely playing a substantial role here as well, and we’d be silly to think otherwise.

The purpose of a competent agent is to maximize his or her client’s overall earning power, which in Bryant’s case means being able to fully leverage his prime years. A seven-year extension now means hitting the market again at 33, which isn’t as ideal as doing so three years earlier. So the real key as far as Boras is concerned isn’t necessarily earning more in those arb years as it is doing so after.

And in order for the Cubs to get Bryant and Boras off of that position, they’re probably going to have to come with something north of $200 million for eight years. Then you factor in opt-outs and escalators to further sweeten the deal. Would 8/$210M get it done? That would offer an average of about $10 million more per season through the arb years and then about $15 million less over the last four years in total.

Now that I’ve said all this, I feel obliged to note that I’m attacking this with all the subtlety and exactitude of a prehistoric stone hammer, so there’s all sorts of other nuance to consider. But the fact of the matter is that Bryant is only going to get more expensive as time goes on. The Cubs need to do everything they can to keep him in Chicago for the remainder of his career, so getting something done earlier means more room to retain and/or attract others.

I’d say the likelihood of anything actually getting done prior to the 2018 is very low, with the odds increasing a bit in each subsequent year. What Bryant gets in arbitration may help to determine when and for how much he signs, so keep an eye on that this winter.

J.D. Martinez hires Boras

When it comes to sluggers getting fat paid, J.D. Martinez is at the top of the list this winter. And his prospects for landing a huge deal just got that much brighter with news that he’d hired Scott Boras. An outspoken advocate of launch angle and getting the ball in the air, Martinez mashed a career-high 45 home runs this past season and figures to be the top overall player on the market.

Now let’s just hope he goes to an AL team so the Cubs don’t have to face him as often in the future.

Otani may stay in Japan

We’ve got a whole feature on this topic already, but I’m including it here because of the tidbit that Shohei Otani may hire Boras as his MLB agent. Kinda seemed fitting, what with the super-agent factoring in the first two segments. There’s also another aspect of the Ruthian pitcher/slugger’s story that should be noted.

In one of many columns I’ve written on Otani, I had accurately sussed out the impending impasse between the various parties involved in the situation. It wasn’t some master stroke of genius or anything, just deciphering the writing on the wall. Which is something those closest to it would surely have made out as well.

I’d not really thought much about this next bit, but a Twitter exchange with BP Wrigleyville contributor Jeff Lamb brought to light the idea that the not-about-the-money talk could have been an exercise in brand-building the whole time. Perhaps Otani’s camp was simply polishing his public image ahead of a defection they knew wouldn’t happen.

It’s an interesting angle and one that makes sense on more levels than one.