Damian Lillard trade: Blazers waited too long to face reality, and now they have a $160M Jerami Grant contract

Welp, it happened. Less than 24 hours after the opening of free agency, Damian Lillard requested a trade on Saturday, per The Athletic’s Shams Charania, who also reports that the Miami Heat, as was widely reported before this official request came down, is Lillard’s preferred destination. 

There will be plenty of talk about whatever team ends up getting Lillard, but for the moment I’d like to look at the team he’s leaving, which is now saddled with a five-year, $160 million Jerami Grant contract, which the Blazers handed out shortly after the opening of the free agency window on Friday. 

On Friday night, I wrote how risky that contract was for Portland with the seemingly inevitable Lillard trade request hanging over the franchise. I didn’t expect that request to come an hour after I woke up Saturday, but I expected it to come at some point. And when it did, that Grant contract was going to look really bad. 

And here we are. 

To me, the only reason to give Grant, a third-option non-All-Star, not only an average annual salary almost identical to that of Jayson Tatum’s current contract, but to commit to that number for five years (I assume the fifth year will be a team option) was to ensure, for one hundred percent absolute certain, that he would be back in Portland, to overwhelm him with a well-above-market offer he couldn’t refuse, because if Grant did leave Portland, Lillard was sure to be right behind him. 

Otherwise, who was Portland bidding against for Grant at that kind of number? He’s a good player, but he’s not that good. And at 30 years old in March, he doesn’t make nearly as much sense on a team that is about to pivot into a youth movement behind Scoot Henderson and Shaedon Sharpe. 

Technically, the Blazers could rescind the offer to Grant. It’s not official yet. Financially, it would be justified. But there’s no way they’re going to do that. After all these other teams have given out their money? Agents would never trust the Blazers again. Portland is stuck with this deal, and not for a short time. 

Indeed, it’s not just the raw money that is going to Grant. It’s the years. I’m no fan of the Mavericks giving Kyrie Irving $126M, and again, I wonder who they were bidding against besides themselves. But at least that’s only a three-year commitment. 

Even if Grant’s fifth year is a team option, four years is a loooooong time to be tied to this kind of money for a fringe All-Star who will be well into his thirties by the end of this deal. Under this new CBA, flexibility will be king, and this deal is decidedly inflexible. It’s not quite Tobias Harris, but it’s not far off. It will be extremely difficult, if not damn-near impossible, to trade him. 

Under normal circumstances, Grant probably deserves somewhere closer to $120 million. Even the $130 million that Houston gave Fred VanVleet (which was also a slight overpay, but Houston has the cap space and, again, it’s only a three-year deal) would’ve been understandable, even for a team without Lillard that wants to remain competitive with Scoot, Sharpe, Anfernee Simons (or whoever they trade Simons for) and whatever comes back for Lillard. 

But five years and $160 million? 

There’s a belief that the deal with Grant has been done for months with Portland, that the announcement was a formality, but I can’t make myself believe that Portland committed to that kind of money, against no competition, months ago. If they did, shame on them. 

I think that high of a number had Lillard’s prints all over it. It was a risky, if not rather outrageous, reach by a front office that either was either willfully naive to the reality that running back virtually the same roster was not going to be enough to keep Dame or has no idea how to negotiate under any kind of pressure. 

Again, show me the team that was going to give Grant that kind of money or that many years, or certainly the combination of the two. If reporting comes out on that, we can talk. I wouldn’t hold your breath under this new CBA. 

I can understand not wanting to lose Grant for nothing. Perhaps that’s why they should’ve looked to trade him last season. That goes for Lillard, too. Cutting ties with a superstar, let alone a franchise icon, is never easy, but the lesson in this is teams don’t have to wait to react to star requests. They can, and should, act in their best interest. 

It was in the best interest of the Blazers to trade Lillard before being forced into a corner. Before they gave Grant $160M. Before they drafted Scoot and all but told the entire league they had no intention of trading him, which in turn all but told the league they were eventually going to have to trade Lillard. Not exactly a prime negotiating position. 

Who’s going to throw a Godfather offer at the Blazers now? What, they’re going to get a couple draft picks and maybe Tyler Herro and Kyle Lowry’s expiring contract from Miami? If they were smart they would take what stands to be a stronger Brooklyn offer (a ton of draft picks, namely, along with maybe Royce O’Neale, Spencer Dinwiddie, Cam Thomas and Patty Mills), but you know how these things go. Once a star says he wants to go to a certain team, he pretty much always goes to that team. 

So now the Blazers are at Lillard’s mercy again. The one thing they’ve done right is draft Henderson. The second the Hornets passed on him, all attention in Portland should’ve shifted to trading Lillard rather than trying to spin this idea that they were going to keep it all together. That was not going to happen. 

In fact, ESPN’s Kendrick Perkins has suggested that Lillard made his trade request known to the Blazers when they all met on Monday. If the Blazers knew this was happening and still handed Grant that money, well, I don’t really know what to say. 

This stuff is hard. Neil Olshey, insufferable as he could come off, got blasted for never making the “big move” but big moves aren’t just sitting out there to be made and the Blazers had some restrictive salary situations to navigate. 

Now they have another one in Grant. On a team that is likely going to lose Lillard for less than he’s worth. Had this request come out of nowhere, fine. But it didn’t. The wind has been blowing this way for a while, regardless of when Lillard actually said the words. 

Same goes for the Wizards and Bradley Beal. That trade was inevitable for years. There was a time when Washington could’ve gotten a huge haul for Beal. But it waited. Didn’t get a single first-round pick in the deal, unless you count the highly protected 2030 pick they got from the Warriors in the subsequent Chris Paul trade with the Warriors. 

The Blazers had far more reason to keep Lillard than the Wizards did Beal, but still, they should have paid attention to what has been right in front of them for the last year. They should’ve gotten ahead of this. Now they could end up starting the Scoot Henderson era by playing from behind.