The Heartbreaking Futility of the Portland Trail-Blazers and Damian Lillard

Loyalty deserves to be rewarded. In an era where the star players have more power than ever before, loyalty is less of an expectation and more of a commodity. Sure, they’ll say all the right things, the city is special, they love the fanbase, they can’t picture themselves anywhere else… then after one setback they immediately start planning their escape. I call this the “Kyrie Irving Principle“. See also: the James Harden Fallacy or the Jae Crowder Conundrum (one of these players is not like the others).

Before you get worried about how loyalty in basketball is dead, don’t worry. Steph Curry, Damian Lillard, Giannis Antetokounmpo, Udonis Haslem, all of these players understand how much they mean to their franchise and their fanbase (again, we should note that one of these guys is slightly worse then the other two). These dudes, like the legends that came before them, have stayed loyal through thick and thin. This loyalty has been rewarded with championship rings and a year-in, year-out commitment to being a great basketball team.

Well, all of them except for one.

Dame’s legend has been carved through his indomitable work ethic. It began in San Lorenzo, California, as a 5′ 5″ freshman starting on the varsity team. After transferring high schools twice before ultimately putting together back-to-back First Team All League campaigns at Oakland High. Only regarded as a two star recruit out of high school, Lillard went to Weber State. He turned himself from two star afterthought into the top Point Guard of the 2012 NBA draft, where he was selected by Portland with the 6th overall pick. At that point, the franchise was still reeling from the devastating Brandon Roy injury and the colossal draft miss that was Greg Oden. Lillard proved not only to be a stabilizing presence, but a transcendent talent. Year after year, Dame has willed the Trail Blazers to success with his inhuman shotmaking. He’s constantly gone punch for punch with the best in the game, even making a Western Conference Finals in 2019.

Want to see the starting line up for the team Damian Lillard was given to go against the Kevin Durant Warriors? I promise you’ll laugh.

Granted: Jusuf Nurkić and Gary Trent Jr. were out with injuries. The Warriors actually had an injured player too. His name was Kevin Durant.

Going to war against the best dynasty in recent years with Mo Harkless and a Twitter politician who couldn’t guard a parked car is… less than ideal.

Now you can see where the problems began to arise. The Blazers front office has continually failed to surround Lillard with the pieces he needs to succeed. Dame is a loyal guy, his PR team has made sure you know that, so much so that “not running from the grind” has become a meme.

But even the guy whose whole brand is built around being loyal has his limits. It’s been the same cycle; team makes new additions, team has great things to say in training camp, team under performs until Dame starts playing superhuman, then his teammates let him down after he drags them to a 5-8 seed. As Jonathan Tjarks puts it, “Dame Time is the most thrilling one-man show in the NBA. The problem is that the clock always runs out”. All of these draft misses and free agency busts keep adding up, and frustration is beginning to take hold.

It’s like when a dude wants to get out of his relationship, but doesn’t want to be the person to break it off. He won’t say the magic words (in this case, “Trade me”), but he’ll try his best to force the other’s hand. Liking pictures of other girls on Instagram, not picking up calls, publicly ranking which teams he’d like to be traded too, subtle stuff like that. Portland needed a gift from the basketball gods to fix this mess.

Guess what? They got it.

Through some divine miracle (or more accurately, blind luck), they find themselves with the 3rd overall pick in the draft. This is exactly the kind of break the franchise has so desperately needed to escape out of the basketball purgatory they’ve been stuck in for years.

But there’s a catch, it’s not as easy as simply getting the pick. What the Blazers choose to do with it will have massive ramifications on not only this season, but for the next decade of basketball in Oregon. On paper the opportunites this presents are fantastic. In practice, the situation becomes much more dire. Why? Well let’s take a closer look.

Joe Cronin and the rest of the front office have three choices:

  1. Stand pat; take one of the three top prospects in what’s been forecasted as a historically good draft, and build out a roster through suplamental moves and free agent signings
  2. Trade the pick for win now pieces; sacrifice your future to try and do right by the best player in franchise history, rewarding his loyalty through years of ups and downs
  3. Trade Dame: throw all the history and sentimental crap out the window, restart with what’s sure to be a massive haul of young prospects and picks, and finally rebuild, while giving Dame the chance to go win a ring

Let’s start with Option 1: standing pat. The number one draft pick will obviously be French phenom/alien Victor Wembanyama. In case you’ve somehow missed it, this is the shit that he can do:

I think we know where San Antonio is going with their pick

That means should Portland stay at 3, they’ll be drafting one of the other top prospects: either Alabama’s Brandon Miller or Scoot Henderson of the G-League Ignite. If not for Wembanyama being the most hyped prospect since Lebron James, Scoot Henderson would be the no-brainer Number 1 pick. His rare combination of speed, power, and control of the game makes him a generational guard prospect. He also has the exact attitude you want in a franchise guy. He’s an obvious pick. Charlotte seems to be infatuated with the far less exciting but still high level prospect Brandon Miller. The Hornets are their own shitshow, but their incompetency might let the Trail-Blazers luck into the best guard prospect in recent memory. Question is, does he fit into an already uber talented but defensive deficient Blazers backcourt in Dame and Anfernee Simons?

Say Charlotte wises up and takes Scoot. That leaves the Blazer with Miller, which, all things considered, is a pretty damn good second option. There’s a reason for the hype, Miller is the type of prospect every team needs in modern NBA. A 6′ 9″ 3 and D wing with good playmaking vision and the potential to become a go-to-scorer. I’m lower on Miller then the consensus, (his stiff handle and lack of burst off the dribble makes me question his success against NBA-level athletes), but he’s still a hell of a prospect, and could be the talented wing the Blazers so desperately need.

That being said, is one talented rookie even enough to overcome an atrocious Portland roster? Jerami Grant, who was the Blazers second best player last year, will be out the door or re-signed for too much cash. He’s good, but not $40 million a year good. Starting center Jusuf Nurkic (who also makes too much money) nosedived this year, and Drew Eubanks offered nothing in his place. Anfernee Simons is a great upcoming talent! Hooray! Thing is, he has the same Achilles Heel that crippled Cj McCollum’s partnership with Dame: he’s short and can’t play defense. Starting one shorter guard who can’t really play defense can be schemed around, starting two is a death sentence in the playoffs. If you can’t stop opposing guards from getting to the middle from the POA (point of attack) guards, your entire defense collapses. Simple as that.

The rest of the roster isn’t much better, outside of Nassir Little, who played admirably last season, has some exciting upside, and may be the only Blazer with a tradeable contract. Shadeon Sharpe looks promising too, but he’s barely 20. Matisse Thybulle’s is a complete zero on offense, Cam Reddish is a hypothetical player, and the rest of the roster would be out of the rotation on any other team. There’s no free agents that really upgrade the Blazers significantly. Draymond ain’t coming, a Grant re-signing tanks cap space, and do you want to give Kyle Kuzma 30 mil a year? and a big star trade is just preposterous without including Dame in the deal. So anyway you slice it, sticking around at 3 might never even move the needle enough for playoff team, let alone a championship one.

So this leads to option number 2: trade the pick. Again, this is a loaded draft. And especially if Charlotte is deadset on drafting Miller, getting Scoot at three makes the pick even more valuable. Henderson is a franchise-changing guy, and the Blazers should get ample compensation. Rumors of the Pelicans as major suitors, could Portland capitalize on injury spectulation (and off-the-court drama) to steal Zion? Maybe Paul George should the Clippers choose to reset? Pascal Siakam, Mikal Bridges, DeAndre Ayton, potentially even a Jaylen Brown deal?

Adding any of these players would be incredible, yet the same question remains; do any of these one guys really put you over the edge? I hate to harp on it, but watching Trendon Watford and Skylar Mays play starter minutes when the Blazers were tanking against the Kings scarred me. Shaquille Harrison played 24 minutes that game! Even swinging for a less star-oriented more balanced trade is still a challenging proposal. Dame needs another co-star to take the defensive heat off him in the playoffs, and I’m not sure the Blazers can get a guy like that and solid bench pieces without giving up too much of their own.

For winning now, this the best shot. But it’s really not a great one, and it’s the kind of hubris that leaves teams watching the guys they traded become stars while they themselves remain scuttling through the middle. Dame turns 33 next year, time is absolutely not in. He’s already shown to have injury trouble nearly every season, how much longer can we count on him for more than 50 games? Once again, no matter you look at it, the Blazers are left with limited moves that produce risky-at-best, catastrophic-at-worst results. The championship window seems to be slammed tightly shut in Portland.

So this leaves us with option number three: trade Dame. Trade the franchise leader in points, the most iconic player in franchise history, a dude who’s given everything to his city and deserves a statue in front of the arena. Trade him away and rebuild. Finally, mercifully, break out of the middle. Break out of hoping for 44 win seasons and some lucky internal player development. Get out of one guy giving everything just to barely get by. Embrace the tank and reset, and allow Dame the chance to ring chase. It’s hard to do, but may ultimately be the right thing. Maybe it’s for the best if the franchise and their player go their separate ways. Forever grateful for each other, but knowing it’s the best for both of them if they move now. It’s bittersweet, but beautiful.

Beautiful. Touching. The stuff Oscar winners are made of. Here’s the catch; we live in the real world, and GMs aren’t stupid. They know the franchise wants to do right by their guy, and naturally they’re going to exploit that. Say Dame wants to force his way to Miami, or Milwaukee, or even Brooklyn, what assets will these guys being willing to give up, and how much are they even able to give? Any contending team will want to add Dame while maintaining the core, and they naturally don’t have the youngest guys.

Brooklyn can do the best (and is my favorite Dame landing spot) by offering Cam Johnson (a restricted free agent) and… Nic Claxton? Cam Thomas? Whatever picks aren’t tied up in all the other star trades they’ve made? Good players certainly, but still not the home run swing the Blazers would like. Milwaukee has like one person under the age of 30 and all their picks tied up from the Jrue Holiday trade. Miami can give you Max Strus, Duncan Robinson, and Tyler Herro? Congrats, you got the Splash Crackers as your young core. Point is, any contender that wants to stay a contender can’t give up enough assets to validate a Damian Lillard trade for Portland.

That leaves the option of screwing Dame over and sending him to any team that will pay the right price. Sacrificing years of love, trust, and respect, ruining a beautiful relationship. We’ve seen front offices ruin relationships with franchise legends, and it sucks for everybody. We don’t want another Kevin Garnett-Timberwolves situation, and I don’t think the Blazers want that to happen either. So they’ll try to send Dame to the team of his choosing. And as much as I respect them for doing so, trading Dame to whichever team he wants will end up screwing the Blazers over. GMs will take advantage of this kindness and rip Portland off. It ain’t a fair world. You can’t do right by somebody without falling on your sword. Cold world.

For those keeping track at home, you might be thinking, “man, these are three pretty shitty options. The future looks bleak.” Well, you’d be right. Years of stupid mistakes and costly missteps have backed the Blazers into an inescapable hell of their own making

So what can they do? Well, there’s always option number 4:

When the anarchy and the void appear to be the best way out, you should really take a look in the mirror ask yourself how much more you can take. It’s a mythological tragedy, the sins of the past catch up and end up damning you.

No matter what direction Portland goes Thursday night, it seems that the Damian Lillard era will end with one deep playoff run and years of constant disappointment. For Blazers fans, this undoubtedly brings up a mix of conflicting emotions. You had the joy of witnessing one of the greatest players of our era suit up for you every night, but the heartbreak of watching his talent get wasted year after year. I hate to say this, but there is no light at the end of the tunnel. LaMarcus Aldridge ain’t walking through that door. There is no quick, easy fix. Whether sooner or later, the Trail-Blazers will have to start over.

So, as a man who’s been a Kings for the past 17 years, I can tell you this: suck it up. You had your shot and missed it. Oh well! No matter what, you’ll always the great memories, the euphoria of the wins, the excitement, and the hope. These are all things that ebb and flow in NBA history, and when you have it you have to hold on tight and enjoy it for as long as it lasts. When it inevitably ends, sad as it may be, we can find peace in the fact that we got to experience it at all. It may not seem like it now, but one day you’ll be right back there, with a hope in your eyes and a dream in your head.

Hopefully it doesn’t take you 16 years like it did for me but hey you’ll get there one day!

At least you’ll always have this:

“You cannot now believe that you will ever feel better. But this is not true. You are sure to be happy again. Knowing this, truly believing it, will make you less miserable now.” — Abraham Lincoln

One response to “The Heartbreaking Futility of the Portland Trail-Blazers and Damian Lillard”

  1. Dominic Marchetti Avatar
    Dominic Marchetti

    I think Damian Lillard should be traded to the Lakers for Dangleo Russell

    Like

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