Will Damian Lillard Win an NBA Championship with the Trail Blazers?

Since 2012, and perhaps since the dawn of the franchise, no player has defined the Portland Trail Blazers more than Damian Lillard. His three-point shooting, 50-point performances, and charismatic leadership have stamped him as one of the best in this NBA generation, if not an all-time great. One thing remains to fill out his impressive résumé: an NBA championship.

But this is where the narrative comes to a grinding halt. As objectively great as Lillard has been, his teams have never gotten close to gold. Their lone trip to the Western Conference Finals in 2019 resulted in a four-game sweep, as the Golden State Warriors squished them like an offending, but hardly frightening, spider scuttling across the kitchen floor. Two trips to the second round and four first-round exits round out Lillard’s tenure.

Will that story change after Lillard embarks on his ninth NBA season this winter? Dia Miller and Dave Deckard tackle that question today.

Dave: So, I’m going to ask a question that’s sensitive for many Blazers fans...for many people surrounding the Blazers in general, I think. Damian Lillard is clearly one of the top three players the Blazers franchise has ever seen. In some people’s eyes, he’s THE best. He just turned 30 years old and just finished his 8th season, meaning that realistically we’re probably closer to the end of his career than the beginning. That’s certainly true of his prime.

By this time in their careers Bill Walton had won an NBA championship. Clyde Drexler had been to the NBA Finals, was on his way to a second appearance, and had just come off of a 63-win season. Lillard’s Blazers haven’t been anywhere near those accomplishments.

Let’s assume, because we’re sane, that Lillard is everything advertised. He is, indeed, one of the all-time greats. This post will not be a referendum on him at all. With that as a given, do you think the Blazers can, or will, win a championship with him before it’s all over? Or will he at least make the Finals in Portland?

Dia: This is definitely a sensitive topic for Blazer fans. I’m not entirely sure why that is, other than the simple fact that we would all love to see It happen and the clock is ticking. I feel like at this point there’s almost a sense of desperation. Dame’s prime is here, and we don’t want to waste it, but does that mean taking drastic measures? Are we willing to take those drastic measures? You and I have discussed those things before. The short answer to your question, is yes, I think the Blazers can make it to the finals before Damian Lillard’s time in Portland is done. More than that, I think they can win a championship. If ever in the history of the NBA there was a player who could will a championship to their city, it’s Damian Lillard.

Dave: Gotta love the confidence! My feelings are a bit more measured, but I want to hear your point of view first. What is it about Dame that makes you think he’s the championship standard bearer on his own? Or are you forecasting the significant help that we’ve talked about prior?

Dia: No one can win on their own, obviously. But as we have talked about before, Dame is the kind of leader that makes the people around him so much better. I think we are just so close. I don’t think we need to completely blow up the team in order to be contenders, but I do think some moves need to be made. With a few calculated moves and Dame’s leadership ability and skill, I think we are in. Look at Lebron. He’s just one player, and he and Dame aren’t the same, but he’s been in the finals 9 of the last 10 seasons. With different teams, and different teammates. I think that’s a solid argument that one player can make all the difference. But don’t confuse that with one player being enough on his own. Because Damian Lillard, though incredible, can’t do It by himself.

Dave: I was going to bring up LeBron James as the only player who’s proven to be in the category you’re talking about. I can’t think of anybody else in our era who’s close. Michael Jordan in the 90’s, obviously. Bill Russell back in prehistoric times? We’re not even talking once per generation. We’re maybe talking 3-4 times in a century someone comes along like that.

I love Dame. Who wouldn’t? But there are so many things that go into making LeBron, LeBron. Talent, skill, and supreme dedication are at the forefront, but also sheer size. LeBron is a physical masterpiece. He’s been unique enough to adapt to a couple different playing styles over his career and he’s handled them like a champ. He’s been able to play big minutes at multiple positions in the lineup and on the floor. Lillard has talent, skill, and dedication, but he’s not a 6’9, 250-lb, agility-packed wonder of the world. I don’t think it’s controversial to say he’s not LeBron.

Short of LeBron, nobody makes the Finals every year. Every non-LeBron championship team in recent memory had a really good point guard, but they also had BIG-time help. Steph Curry had Klay Thompson, Draymond Green, and Kevin Durant. Tony Parker had Tim Duncan and Manu Ginobili. Kyle Lowry had Kawhi Leonard. Jason Kidd had Jason Terry, Caron Butler, and Dirk Nowitzki.

I love Jusuf Nurkic and CJ McCollum. I’m just not sure that they’re enough to get the Blazers to the Promised Land. I’m fairly sure the whole rest of the roster isn’t. I see Lillard like a choir director. He may have the most amazing voice ever, but ultimately the ensemble will only be as good as its components, no matter how much he tries to coax out of them.

For me, the conversation turns away from Lillard’s own ability and straight towards Portland’s capacity to surround him with players. For the most part, they haven’t done that. Drexler had far more support than Dame has. Walton helped make his supporting cast better, but Maurice Lucas and Lionel Hollins were both All-Stars, at least. Short of a Big Deal™, I don’t see a ton of ways for the Blazers to get players that would push them over the top.

I want to be convinced. Help me?

Dia: I absolutely agree that Dame and LeBron are different, and I’m not necessarily implying that Dame will do the same thing LeBron has. I agree with your sentiment about a lot of this depending on Portland’s ability to surround him with the right support players. I think this leads us to a familiar conversation about if the Trail Blazers can and will make big moves, and if that will make the difference. We just keep coming so close and falling so short. We made It to the Western Conference Finals just last season. We were so close. That gives me hope that we aren’t far. We need some changes. We need to fill some holes, but we are close. What are the chances that we pull in a star? Or a semi-star. Someone to be the Scottie Pippen to Dame’s Jordan? I think I’m a reasonable, realistic person overall, but I am self-aware enough to know that I tend to be a dreamer and overly optimistic when It comes to the Trail Blazers. My dreaming, overly optimistic self thinks that we could pull in a big-ish name. There has to be a draw for a player like that to get to play with some of this squad, even though it’s a smaller market. I can’t help but think it’s possible. Right?

Dave: That is, and has always been, a two-stage question for the Blazers.

First, does the front office see the need for a change? Lillard and CJ McCollum are a seductive pair. They’re scoring guards playing in an era that favors such. The Blazers don’t just build their basketball schemes around them, their entire brand rests on the shoulders of the starting guards. They’re Neil Olshey draft picks. He can take full credit for their excellent contributions. There’s plenty of incentive to keep them together.

If somebody promised you a job for $20 million per year, then said you could keep it or trade it in for a 1 in 6 chance at getting $800 million, you might just figure that, even if the jackpot number is higher, $20 million per year for the next 20 years is plenty...way more than most people get. Fielding Lillard and McCollum, the Blazers will always have that steady salary.

I believe the Blazers would be willing make a deal if they felt it had a good chance to lead them to a championship. I don’t think they’re willing to mess around with trades that would make them marginally better, even if that would technically put them closer to a title. The good team they can sell to their fans right now is more attractive than a somewhat-better team they might build towards.

Is a clear championship move that would overcome the franchise inertia out there? Maybe, but that bar is pretty high. The Blazers probably need a 3-and-D wing to make that leap, literally the most coveted position and skill set in the league right now. That makes it even harder.

If the opportunity opens up—which is not guaranteed—they’re going to need to ask whether they can fill that position any other way or whether it would be easier to replace the players they’d trade to get that guy. I presume they’d do the deal and worry about the rest later.

If that opportunity doesn’t open up, they have to ask whether they can make another move that at least leaves a different problem to be solved after. Maybe they leave a hole elsewhere that a modest free agent could help fill. But again, are they willing to take the baby step to make the big leap shorter in the end without that big leap being guaranteed?

Time is the hidden enemy here. We’ve known this moment was coming for years. McCollum and Lillard are rounding the 30 pole. It’d be nice to get them three really good shots at making the NBA Finals. If the Blazers are going to take a risk, they need to do it soon. If time or injury eats into Lillard’s productivity, this becomes a whole different discussion. At that point, we’re not talking about leaping a gap but finding a whole new route.

So I guess, in the end, the question comes down to whether a championship is worth risking what they already have, or is good play and great public relations enough. Want to tackle that next week?

Dia: That is definitely a whole other discussion. Probably one worth having. It almost feels right now as though we are stuck between a rock and a hard place. The current team is loved, and while I think most fans would be okay making big moves if It leads us to a championship, that’s a big if. I still hear people talk about all the guys we let go of after our Western Conference Finals appearance last year. The fact is, if we make big moves and don’t win a championship, that’s going to be a hard pill to swallow. But what if we do? Good discussion as always, Dave. You’ve definitely got me thinking.

What do you think, Dear Readers? Are you willing to forecast a title in Damian Lillard’s future? If so, will it be with the Blazers or elsewhere? Add your voice to the conversation in the comments section.