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Matt Chapman Wants Extensions And Cindi Is Ready

Oakland Athletics v Seattle Mariners
Talk about good extension.
Photo by Rob Leiter/MLB Photos via Getty Images

I’ve been trying to explain to Cindi all day how the extensions Matt Chapman is referring to have nothing to do with anything she is learning in her cosmetology class. Try to deter a stubborn 16-year old, though ... having learned the distinction, Cindi is still proclaiming herself to be an expert, insisting that it would be “cray cray” not to give an extension to a Taurus who is also a super-hottie. Sounds like a lot of bull to me.

If you missed it, Chapman’s prelude to FanFest was a plea for the A’s to ink Marcus Semien, and himself, oh and also Matt Olson, to contract extensions, an idea he may not have run by his own agent, a certain Scott Boras — a man known for his disdain for extensions and his love for early free agency.

Extensions for any, let alone all three, of them would cost quite a bit more than just offering quality barbering. So today let me opine on how I suspect the A’s front office will approach a dilemma that is as frightening as it is exciting.

Oakland’s timeline for considering extensions is governed largely by the new stadium. Billy Beane has, many times before and again at FanFest today, referred to a new stadium as the avenue for the A’s to shift practices from developing great players who get paid elsewhere, to keeping some of their homegrown talent.

Now there are caveats beyond just the reality that keeping some of your stars is to be distinguished from being able to keep all of them. It would be a step forward for the A’s just to keep their best players for the full 6 years before free agency, because often the front office has had to move key players as they hit arbitration. Arbitration alone often jumps a player’s salary tenfold, especially in that 5th or 6th season.

Also, even if you can keep all your stars it doesn’t mean you necessarily should. If offered a bottomless pit of payroll, Oakland could make Semien, Olson, and Chapman faces of the franchise and before long you would have a team similar to ... the Philadelphia Phillies, whose beloved stars Ryan Howard, Chase Utley, and Jimmy Rollins were as popular as “The Golden Girls” until they became all too much like them.

The A’s are really good at paying for present performance and not for past performance, for grabbing a player’s best years without paying even more for their worst seasons. And given that Oakland’s payroll is still far from bottomless, difficult decisions will have to made.

My own suspicions on how the front office will move forward:

First and foremost, though Chapman is quoted citing spring training as a time extension talks can heat up, I don’t foresee the A’s getting serious with any player before the new stadium passes each and every hurdle — and according to Dave Kaval at today’s FanFest, without setbacks that figures to be sometime this summer.

Marcus Semien

Semien’s contract is the most urgent, simply because he reaches free agency at the end of the 2020 season. It was presumably Semien’s situation, not Chapman’s own, that prompted the A’s 3Bman to speak up now.

I think the A’s will make an effort to keep Semien beyond 2020, but not that far beyond — which could potentially break down talks between the two sides. If and when the stadium is “for sure,” I can see Oakland making a decent offer to keep Semien under contract through 2022 (through his age 32 season). Maybe if I squint I can add a year just because that coincides with the opening of said new stadium.

What that also does, of course, is keep Semien under contract through the seasons where he is likely to get a lucrative, multi-year free agent deal. Does Semien want to delay free agency until he is 32 or 33, and still not be assured of playing his entire career with the A’s? Or will he seek “a 5-6 year extension or bust”?

We may find out, because given his local ties, his sterling character, and his on field performance, I have to think the A’s will at least take a shot at keeping Semien beyond 2020, but I can’t see them offering very many years. Especially considering that we haven’t even gotten to the Matts yet...

Matt Chapman

Generally, when the topic of a Matt Chapman extension comes up it is quickly shut down by fans who cite two truths: Scott Boras doesn’t let his clients sign extensions and the A’s don’t give out the kind of contracts Chapman will command.

I am of a different opinion. If the stadium gets the green light, I have a feeling the A’s are going to make an effort to make Chapman “the face of the franchise” moving into the new stadium. I don’t know if they will be successful, but I will be surprised if they don’t make a genuine effort.

Meanwhile, two factors give me hope that Chapman’s stance won’t go the way of most Boras clients. One is that Chapman just does not come across as a typical Boras client who says, “Get me the best financial deal and tell me where I’m going.” Chapman has publicly voiced, on multiple occasions, his interest in an extension, even using language such as that he has “instructed Boras to listen to talks”. The client should, ultimately, be the one in charge of a negotiation, but rarely is this actually the case — especially clients who select, for their representation, an agent known for being a shark dedicated to grabbing the most money for his client. But Chapman does not seem like “most clients,” just another reason, hopefully, to love him.

Also, recent years have not been as kind to Boras’ tactics. Boras seemingly ran, manipulated, and owned negotiations for years, playing and winning games of chicken with team after team. Then something shifted. When a Dallas Keuchel holds out all the way into the regular season and then comes crawling back for a one-year deal comparable to a qualifying offer, you know who lost. Boras may be coming around to fair-market extensions, not because his philosophies have changes, but because the market has changed and the Bregmans are getting paid better than the Keuchels.

I don’t, of course, think Chapman is about to turn his career into a charity and give the A’s a 50% hometown discount. Oakland will have to reach deep into its pockets to retain Chapman, but the timing might be just right. Chapman’s current contract takes him through 2023, the year the A’s expect to move into their new stadium. For the first time, the money for a sizable extension might be there and for the first time Boras may be ready — or simply instructed — to listen.

Matt Olson

I have no doubt the A’s would like to keep Matt Olson around for years to come. Trouble is, Oly is current the “middle child” — neither the natural face of the franchise Chapman is, nor with a contract that about to expire.

As a result, in all likelihood the window for an Olson extension opens the widest via the failure to sign one or both of Semien and Chapman. If the A’s decide it’s too soon to start giving out bigger money, and Semien walks, odds of an Olson extension rise. If talks with Chapman fall apart, money opens up for Olson.

As he has been for much of his career, Olson is “Chapman Jr.,” the less famous, less talked about, more underrated but still greatly appreciated, Matt.

That being said, perhaps being the middle child will help instead of hurt — unlike Semien, Olson’s contract won’t be up until Oakland is moving into their new stadium and playing with more revenue. Unlike Chapman, Olson will only cost “a truckload” instead of “a truckload and then a lot more”.

So it’s conceivable we could be seeing a lot more of Olson, even that he could wind up being a face of the franchise. But my guess is that it can’t quite be Plan A and that the front office will be focusing first on Semien, hard on Chapman — and then we’ll see where we are.

So much to ponder. And we haven’t even mentioned Ramon Laureano, or any pitchers. This stuff is complicated — I’m glad it’s not my job to sort it out.