Tyler Herro may be coming off the best year of his career, and he may feel he’s worth a huge contract extension, but that line of thinking is making his upcoming contract decision an absolute nightmare for the Miami Heat. That’s because even though Herro may strongly believe in himself, he’s not currently worth $40 million per season in today’s NBA economy.

Much less a full max extension, which would give him a three-year, $50 million payday. And that’s going to make the next couple of months absolutely impossible for the Heat to navigate.

Officially, Herro becomes contract extension eligible on October 1. That extension window runs through the end of October. If the Heat and Herro don’t agree to an extension during that window, the Heat would then have to wait until next summer to hammer out a new deal.

At the same rate, Herro would then have the opportunity to test unrestricted free agency if he so decided.

What type of raise will Tyler Herro demand?

In theory, the expectation would be that Herro is going to demand a huge raise. He has every opportunity – and reason – to do so. But whether that will actually be the case or not remains to be seen.

It’s only natural for Heat fans to be skeptical at this point. After all, in the middle of his prime years, there’s no real reason for Herro to take less than what he believes he’s worth. Being named to the All-Star team this past season, it’s hard to think that Herro won’t ask for at least some sort of raise.

Perhaps we’re all wrong. Maybe he does elect to do the team a favor and sign a team-friendly extension, one that maybe only gives him a slight raise. Maybe something in the $35-$38 million per year range.

But if Herro holds strong at his demand, which will likely be asking for an extension worth between $40 and $50 million per season, the Heat may have no choice but to kick the tire down the road on a decision. Or, perhaps more drastically, the Heat may have to make the bold decision to trade him.

That would suddenly become more of a possibility if Miami does get the impression that Herro isn’t going to back down from his huge contract demands.

Of course, there’s no way to know with certainty what exactly will happen over the next two months. It’d be foolish to say that anyone knows how this summer will end between the Heat and Herro.

One thing is for sure, though, and it’s the fact that the Heat are in a pretty undesirable situation. And what they end up deciding to do with Hero will, without question, greatly impact the next few years of their future.

The unfortunate part about all this is that there are no easy answers. And no matter what they end up doing, I’m sure there will be critics on both sides of the aisle.