Has Damian Lillard complicated Celtics-Jaylen Brown negotiations?

Is Damian Lillard quietly complicating the contract negotiations between the Boston Celtics and Jaylen Brown? 

When Damian Lillard requested a trade from the Portland Trail Blazers, the league was completely flipped upside down. And, effectively, as you would expect, it has, to a certain extent, brought NBA Free Agency to a standstill. That said, what has complicated everything this offseason is the fact that Lillard seems deadset on being traded to the Miami Heat.

For now.

That could change especially if the Blazers continue to hold out from striking a deal with Miami. If the Blazers do convince Lillard and his camp to explore other potential landing spots, there are two that make the most sense – the Philadelphia 76ers and Boston Celtics.

The one intriguing option is the Celtics.

On paper, even if the Celtics gutted their roster, which they likely won’t have to if they made Brown and picks available to Portland, they’d have a trio of Jayson Tatum, Lillard, and Kristaps Porzingis. That’s probably the second-best trio in the league, just behind the Phoenix Suns.

Objectively, it’s not that outlandish for the Celtics to be able to sell Lillard on that.

The Boston Celtics are a legit threat to steal Damian Lillard from the Miami Heat

Clearly, if there’s one team that the Heat should be wary of, it’s the Celtics. They have the market, the competitive talent, and the necessary assets that would appease the Blazers in a potential Lillard trade.

If the stars were to align for Boston to pursue Lillard in good faith (from all sides), the one premier asset that would likely be used is Jaylen Brown. Interestingly enough, he’s currently eligible for the supermax contract extension that his camp and the team are reportedly negotiating.

The window opened for him to sign an extension on July 1, but it still hasn’t been signed yet and you can’t help but wonder why.

The NBA conspiracy theorist inside me makes me question whether the Lillard trade request has had any impact on the contract negotiations between the Celtics and Brown.

Maybe these two aren’t related at all but I can’t help but think that perhaps the Celtics are trying to linger in negotiations before committing the supermax to Brown. Once Brown signs the supermax, he is ineligible to be traded for one year. That means if Lillard were to come around to the idea of being traded to the Celtics (after Brown signs the extension), Boston wouldn’t be able to use arguably their best realistic trade asset in a deal.

Again, maybe it’s nothing. Maybe this is just the complexity of negotiating a supermax contract extension. Or, maybe, the Celtics are trying to play both sides here. Either way, you’d have to imagine that there will be some kind of resolution sooner or later. Unless something drastically changes soon, the expectation should be that Brown will sign his huge extension with the Celtics.