Damian Lillard's trade request doesn't make him a villain, and now it's time for Trail Blazers to find amicable end

The Miami Heat’s package appears to start with Tyler Herro and Duncan Robinson to make the money work

It would’ve been nice for Damian Lillard and the Portland Trail Blazers to have this storybook happy ending, for a player’s loyalty to be rewarded in the form of a championship, a Finals MVP and a shot to the critics.

But he’ll have to settle for a retired jersey, the sun of South Beach and a few snickers from critics who warned him on speaking so strongly about running from the grind. It’s at least looking that way so far, with the Heat in pole position for Lillard’s services and a massive contract extension scheduled to kick in two years from now.

According to sources, Lillard wants to get to Miami. Philadelphia, even with MVP Joel Embiid, isn’t on his list.

So Miami it will likely be.

As has been displayed with the Golden State Warriors, a two-timelines system doesn’t work in the NBA. Either you’re in or you’re out.

And the Trail Blazers, in keeping their draft picks over the last couple of years, positioned themselves to build for the future while trying to keep Lillard close to satisfied. They have the talent who could be good one day but are nowhere near Dame’s Time.

Their prerogative.

Perhaps they overestimated Lillard’s patience and took his public statements as gospel he could never be pushed out while still in his prime. Perhaps they underestimated how Lillard could be so connected to the Northwest region, the Blazers franchise and still make a decision that’s best for himself.

Either way, this is where we are — an inevitable place on the second day of free agency after it appeared clear to Lillard the Trail Blazers franchise has overpromised and underdelivered for the last few years.

Damian Lillard is coming off a resurgent season with the Portland Trail Blazers. (Rich Schultz/Getty Images)
Damian Lillard is coming off a resurgent season with the Portland Trail Blazers. (Rich Schultz/Getty Images)

And with Lillard coming off a resurgent season, an All-NBA one following missing a big stretch of 2021-22 with an abdominal strain, perhaps he sees his basketball mortality flashing in front of his eyes. He’ll be 33 in a couple weeks — older than Charles Barkley when Barkley requested his second trade to a contender, to the Houston Rockets in 1996, older than Kevin Garnett when Garnett finally realized the Minnesota Timberwolves were no good for him, but still young enough to put together great years and be a reasonable facsimile of himself for a real contender.

Barkley was already breaking down after giving Philadelphia nine years and then Phoenix four. Garnett, for the championship he led Boston to in his first year, was actually closer to catastrophic injury than anyone realized.

Luckily, he got that title in 2008 because in 2009, a serious knee injury derailed the Celtics’ chance at a repeat and in 2010, the once-boundless Garnett seemed to run out of gas in Game 7 of a classic slugfest with the Los Angeles Lakers — fatigue and all the Minnesota miles caught up with him when nobody expected it.

For Lillard, one can only hope he doesn’t experience the same fate, although a ring would seem to make everything else on the back end worth it.

It doesn’t make Lillard a villain to want out, he’s been a model citizen and hasn’t acted a plum fool to get his way like some of his peers. Has it been slightly annoying? At moments, but there’s nothing wrong with answering a few hypotheticals to keep the pressure on the incumbent organization.

It was pressure, though, the Blazers didn’t feel. They knew Lillard appreciated how important he was to the Portland community, how he gave the Blazers credibility among the sponsors and corporate folks we don’t think of in these cases.

But it wasn’t going to be enough to keep him forever and now they’re faced with sending him where he wants to go — an emotional no-trade clause in a sense, similar to Garnett in 2007. It would be bad form to send Lillard anywhere he doesn’t want to go just because it’s the “best deal” — preserving a long-term relationship with arguably the franchise’s best player (apologies to Clyde Drexler and Bill Walton) should trump haggling over a particular draft pick or two.

After all, they’ve got a jump-start on this rebuild, selected Lillard’s replacement in Scoot Henderson a week ago in the draft and have Shaedon Sharpe and Anfernee Simons to build around in the interim.

The Miami Heat’s package appears to start with Tyler Herro and Duncan Robinson to make the money work. And Jimmy Butler has made it known he wants Lillard as a running mate — feeling like a match made in hard-ass heaven.

Butler loves taking big shots, but Lillard relishes it. Butler wants to make the right play, while Lillard wants to deliver the dagger — with that said, we would be playing in Game 18 of the NBA Finals if Lillard was on the Heat with Butler and Bam Adebayo.

But then again, one can picture Lillard playing with just about anyone who’s focused on winning, which would make a bunch of teams place calls to general manager Joe Cronin and the Blazers just to see if a deal can be consummated.

Lillard coming East would certainly eliminate all the talk about Miami having a lucky run to the Finals, and having a bankable star in the Eastern time zone would make the league enormously happy — along with making a compelling East a lot more compelling next April, along with Boston and Milwaukee.

Lillard’s conduct with Portland means this won’t turn out like James Harden’s first trade request (out of Houston) or Kevin Durant’s summer trade request out of Brooklyn — the one that was rescinded and then reinstated after Brooklyn’s season imploded before the trade deadline.

Harden acted up on his way out of Houston, then acted up on his way out of Brooklyn, apparently to get to Philadelphia where he now, stop if you’ve heard this before, wants out. Lillard has too much basketball character to act out, which means Portland would truly have to convince its departing star to go somewhere besides his desired destination. They could claim signing him to consecutive deals and paying him is where the organizational obligation starts and ends, and in theory could be correct.

But forcing a trade for whatever reason or claiming Miami isn’t offering anything reasonable would be a bad look for an organization that can’t afford to screw this up.

The Blazers made their long-term choices in the best interest of the franchise and now Lillard has made his. It’s time, perhaps a little past time, to end this amicably. Send him to Miami — and buy courtside seats for the Finals down there next June.