The Miami Heat must figure out their future with Tyler Herro quickly, avoiding the same mistakes they made with Jimmy Butler. That means the Heat either must extend Herro to a contract now or move to trade him before things get ugly, or he has an opportunity to leave in free agency.

Should the Heat make the same mistake with Herro that they did with Jimmy, it would paint a pretty unflattering picture of the state of this team’s front office.

If the Heat has anything going for them, it’s the fact that Herro is unlikely to make the stink that Jimmy did if he doesn’t get his way. If Miami decides they want to see Herro play out this season, rather than pay him the $40-50 million per year extension that he’s going to be seeking, I find it hard to believe he’s going to throw a temper tantrum to force his way out of town.

Still, that doesn’t make this situation any less risky.

If the Heat pay Herro now

On October 1, Herro becomes eligible to sign a three-year, $150 million max extension. That’s what he’ll ask for, and I’d have to believe the Heat will say no. But, there is a chance the Heat will offer an extension at a discounted price.

What that discounted price may be remains to be seen. Whether Herro would accept it is also a question in itself. But, either way, extending Herro now all but eliminates any flexibility the Heat has over the next 10 months, especially if it’s at a higher price point.

Unless Herro is willing to take a $35 million per year extension, there’s really no real value in the Heat extending him now.

If the Heat wait until after this season

On the flip side, if the Heat decide to wait until after this season, there are even bigger hurdles. If the Heat doesn’t extend him in his October window, they’ll have to wait until after the season to negotiate. At that point, it’ll be in Herro’s best interest to just wait until free agency opens to see what other offers there may be on the open market.

Going down that path would open the door to the Heat possibly losing Herro for nothing on the open market. I can’t imagine that’s something they’d want to risk. But as they hope to maintain ultimate financial flexibility, it may be a route they have to be willing to take.

That being said, I’d have to imagine that this is probably the most likely scenario playing out over the next NBA calendar year.

If the Heat shops him on the trade market

But even if the Heat did get to a point where they’re open to trading Herro, it’s not that simple. In the final year of his contract, with the uncertainty of an upcoming extension, it’s likely that the Heat would have to accept pennies on the dollar on a trade now. Plus, I’d be shocked if the rest of the league values Herro as much as the Heat does.

But this is kind of the bed the Heat has made for themselves. The important thing for now is that they choose a path forward and stick to it. That’s the big mistake that they made with Jimmy. And it cost them dearly.

Did the Heat learn anything from the entire Jimmy experience? We’re about to find out pretty quickly with how this Herro situation plays out.