The Spurs extending Leonard is all tied up with whether Duncan and Ginobili retire

Kawhi Leonard is eligible for an extension this year and the Spurs will have until the last day of October to decide what to do. Because of Leonard's play -- but also because of the way the market currently values wings with size -- Leonard is probably thinking about a max extension. After The Finals win, he seemed confident the Spurs and his agent would come to an understanding.

Yet there is no news on where the franchise stands on that. The Spurs are notoriously secretive, so that's not exactly shocking. But with Tony Parker already agreeing to an extension, it seems logical to assume Kawhi is next in line. That's why the lack of news seems less like a pregnant pause and more like the silent treatment. What's the hold up?

Unfortunately for the franchise's rising star, the fate of the fading pillars might mean he'll have to wait a little longer for his due. But I'm getting ahead of myself. To truly understand the situation, let's look at the team's cap numbers with an estimated Leonard extension and compare that to what it'd look like if The Hand enters free agency.

If Leonard receives a max extension

Here are the Spurs' salary commitments for the 2015/16 season, assuming Kawhi is extended for the max and Ginobili and Duncan retire:

Tony Parker $13,400,000

Tiago Splitter $8,500,000

Boris Diaw $7,000,000

Patty Mills $3,578,947

Kawhi Leonard $16,625,000

Kyle Anderson $1,142,879

Total                     $50,255,826

The salary cap is expected to be set at $66.5 million. So the Spurs would have, at the most, $16 million and change in cap space. Now, the maximum contract for players that have been in the league for more than six years is 30% of the cap, which would amount to $19.95 million. So say goodbye to fantasies that include LaMarcus Aldridge/Marc Gasol if you're harboring any.

But the bad news doesn't stop there. To actually get to use the cap space, the Spurs would have to make some serious sacrifices: the team would have to renounce all of their free agents in order to wipe away their cap holds. Here's what a cap hold is, courtesy of Larry Coon:

Cap holds are "placeholders" for players the team is expected to sign in the future. For example, a team is expected to sign its unsigned first round draft pick, so an amount is reserved for this signing in the form of a cap hold. A team $10 million below the cap with $4 million in cap holds really has $6 million in room.

Cap holds for Danny Green, Marco Belinelli and Jeff Ayres along with Cory Joseph's qualifying offer would leave the Spurs with around $6 million in cap space. So if Leonard gets an extension, the Spurs would not have max room even if Duncan and Ginobili retire and they would have to renounce all of their free agents (including Danny Green) to have substantial room, which would leave them with a hole at shooting guard and no depth whatsoever.

Simply put, an extension guarantees the Spurs five years of Leonard but takes them out of the run for the top free agents they would need if they hope to replace the production of Duncan and Ginobili.

If Leonard doesn't receive an extension

If the Spurs decide not to extend Leonard and let him enter restricted free agency instead, next off-season he will be on the books for just $4,045,894, which is the sum of his qualifying offer. They could have enough cap space for a max contract while still retaining the ability to match any offer sheet Leonard signs as well as Danny Green's Bird rights.

The problem there is that it requires Kawhi to be on board for another year without financial security, or things could get messy. I covered this at length already but the gist is that if he does break out and becomes a star and the Spurs let him reach restricted free agency, nothing is stopping Kawhi from waiting to see who the Spurs manage to sign and potentially pushing for a shorter contract, likely with a early termination option after the third year.

Whatever money he loses in the short term, he could gain by entering free agency earlier for his third contract, after the league's new TV deal results in a higher cap and higher contracts. And the Spurs would have to either let him go or acquiesce and potentially face a situation similar to the Wolves' with Kevin Love in a couple of seasons.

If Tim Duncan and Manu Ginobili retire, the Spurs would be foolish not to go this route because they will need the type of significant infusion of talent only ample cap room can provide them. But if they strike out, what's keeping Leonard from exploring his options in two years?

So which is the best way to go? Well, it's not that simple, because...

It all depends on what Tim and Manu decide to do

You've probably noticed that I assumed Ginobili and Duncan were retiring in both scenarios. But what really, really complicates things is that there's no way of knowing if that will happen. And their decision is so important that it looms over every other move, including Leonard's extension.

If the Spurs go into next season knowing that this is, unmistakably, the last season Ginobili and Duncan will play, that simplifies things exponentially. They would then swing for the fences, letting Leonard enter restricted free agency, going for a difference-maker at the power forward or center position with their cap space and bringing back only Kawhi and Danny Green.

If they know for sure Duncan and Ginobili are not retiring, they would lock Leonard down with an extension and bring back Green and the other guys on short contracts for one more run. Then in 2016/17, with Duncan and Ginobili retired, the front office would have good players on expiring contracts to trade for another star, with a core already in place.

The problem is not even Manu and Tim know for sure what they are going to do. Duncan said he would try to hold on for as long as he could but he has thought about retirement. Manu said his decision will depend on how he feels this upcoming season. So there is no risk-free course of action here. The front office will have to speculate about Ginobili's and Duncan's future and make tough decisions without certainties. And those decision will directly affect how they deal with the contract situation of the guy Pop has tabbed as the future face of the franchise.

I want to make this clear: the Spurs won't lose Leonard, at least not in the short term. The rules regulating restricted free agency pretty much assure them of his services for at least two years after his rookie contract is up. But it's still curious how Leonard's contract situation mirrors his on court status and it will be interesting to see how he reacts to it.

Leonard won Finals MVP last season and seems primed to make the leap into bona-fide stardom. He bowed out of Team USA to focus on his game, he's healthy, confident and ready to assert himself more. But for as long as the Big Three is alive and well, the Spurs will never truly be Leonard's team. He's aware of it. There's nothing he can do about it and, by all accounts, he's fine with waiting for his turn. He knows his time will come.

Will Leonard be as patient when it comes to his financial future? Is he fine waiting for the franchise to see what Ginobili and Duncan will do before securing that first big payday? No one would blame him if he wasn't. In fact, it's bordering on unfair to expect him to. But it seems like the burden of bridging the ages will not only be an on-court thing for Leonard. Hopefully, he will show the same trust for the front office he has for Pop and will give up a bit of financial security to allow R.C. Buford to have as much room to maneuver as possible.