The New York Knicks have ended one of the longest Finals droughts in the league at 27 years (and are just one win away from securing their first title since 1973). The eyes of the sports world are on their series with San Antonio, and here in Portland, it means the three decades (going on four) drought the team has been dealing with will last at least another calendar year.
But what if Portland were playing in the Finals this year?
What if they made moves the Knicks or Spurs have made, or some combination of them? Would they be in the Finals this week, playing for the second title in franchise history? Or just another team missing the final piece to be a championship contender?
It took the Knicks quite a few trades and some luck in the draft, and the Spurs had to endure a few terrible seasons and the draft lottery going their way to land here.
Could Portland have pulled off a similar jump to the big dance if they pulled the “right” triggers in an alternate timeline?
We asked Bryant Knox (BK) and Casey Mabbott (CM) to share their thoughts on the moves Portland could have made and to ultimately decide whether they believe their choices would have resulted in a championship-worthy roster.
- In February of 2023, Portland traded Josh Hart to the Knicks for Cam Reddish, Matisse Thybulle, Ryan Arcidiacono and a first-round pick, which was used to select Kris Murray. Thybulle and Murray are still on the team. Would you be willing to reverse the deal and keep Hart here?
(BK) To me, this is an easy “yes.”
Although Hart’s scoring can waver, as we’ve seen most recently in these 2026 NBA Finals, he’s a trustworthy 35 percent 3-point shooter for his career (41.3 percent this season), and he’s the definition of a stat-sheet stuffer who doesn’t actually chase stats to the detriment of his team.
Hart’s ~$20 million annual salary is far better bang for your buck than anyone the Trail Blazers received in return, especially considering the main piece was Cam Reddish, who played 20 games with Portland and has gone downhill since.
Again…to me, this is easy. Give me Hart back, no questions asked.
(CM) The return for Hart looked promising at the time, but now that we know he could be a key cog on a championship contender, I would rather have kept him here. Hart was brought here as a potential running mate for Damian Lillard and was traded away just one year later, before he could truly showcase what he could do here. Now, three years later, he is a critical piece of a team that is insanely similar in build to the way many people thought Portland should build around Dame. Thybulle is an elite defender, and I would like to keep him, but I think Portland probably could have brought him here in another deal. Reddish isn’t here anymore, and Arcidiacono never played a game here, so you essentially traded Hart for Thybulle and Murray, which is still a good deal, but it didn’t put Portland in contention. So, I would rather keep Hart and hope his heroics in the playoffs in NY would happen here as well. For some reason, Portland really loves trading away talented shooting guards just before they hit their peak, or, in the case of CJ McCollum, failing to trade them until well after their peak has already happened.
- It has been rumored that Damian Lillard wanted Portland to keep Hart here and trade for Mikal Bridges, but given what we know it took to land Bridges (five 1st-round picks!) and Brooklyn was not willing to send Bridges for the #3 pick, how much would you be willing to give up to bring Bridges to Portland?
(CM) I like what Bridges does as one of the game’s best two-way players. Still, I also have to wonder how crucial he would be to a championship run, especially if you can get Thybulle to play a similar role and give up four fewer first-round picks, or ideally not have to give up any first-round picks. If Portland kept Hart and traded the #3 pick for a veteran forward or center, we wouldn’t even need Bridges, most likely. They could trade another player or a pick to get a good defender, we know they got Jrue Holiday in another deal by giving up Anfernee Simons, let’s assume they could again pull that off and perhaps have two great defenders here to support Dame on the perimeter. Bridges is a really good player; I don’t know if multiple first-round picks are worth it to bring him here.
(BK) I like where Casey’s head is at, in that Thybulle, at his best, can give you a lot of what Bridges offers without sacrificing your draft capital and committing major money to a maybe-star, maybe non-star.
But here’s the thing: Availability is, as the cliché goes, the best ability.
Since 2023-24, Thybulle’s first season in Portland, he has played in 110 out of a possible 246 regular-season games—a roughly 45 percent attendance rate.
Bridges? He’s played in total 246 out of 246 games in that stretch.
And the year before? Bridges played in 83 out of 82 regular-season contests. (You read that right.)
As far as the trade goes, five picks is tough, so I’d try to add an appealing player piece into the deal to save a pick or two. But the trade market was different then than it is now.
The Bridges trade package will always be put under a microscope, but he’s also the player who had back-to-back game-sealing steals in last year’s postseason, and he’s the guy who scored 20 points on 8-of-13 shooting (4-of-6 from deep) just days ago in a critical Game 2 of the NBA Finals.
Whatever the price tag, Portland, aka Bridgetown, USA, would have loved him.
- OG Anunoby was traded from Toronto to New York in December 2023, and the assets required were not earth-shattering. If a trade for Bridges would not be realistic, what would you deal for OG?
(BK) On June 10, 2026—Game 4 of the NBA Finals—OG Anunoby became a New York Knicks legend.
Three years prior, the Knicks acquired the swingman in December for RJ Barrett, Immanuel Quickley, and a 2024 second-round pick. New York also sent out a few other ancillary players, but there’s a lesson learned here:
The Blazers could have gotten a potential Finals hero at a much better price than Bridges.
Realistically, the Blazers would have dealt for OG in the summer, when Portland was shopping the No. 3 pick in an attempt to convince Damian Lillard to stay. Considering where Scoot Henderson is today, dealing that No. 3 pick feels like a no-brainer, and doing so would have potentially replaced the young prospect Toronto otherwise wanted in return.
The risk, of course, is not knowing if OG alone keeps Damian Lillard in town.
To me? It’s worth the risk, knowing everything we know now. If Dame stays, amazing. If not, you have another defensive maniac to pair alongside a rookie Toumani Camara (acquired in the Dame trade) with a higher offensive ceiling.
That’s a risk worth taking. And it’s one I’m comfortable taking in this situation.
(CM) OG is a guy I think would do really well here, and Portland would have the assets to pull off a similar deal. In my opinion, OG is more important to a title run than Bridges, even if, until recently, Bridges was the more popular name. Toronto didn’t want a superstar in return, and it’s possible Portland could have just traded a first-round pick and Shaedon Sharpe and made a similar deal happen. In an ideal timeline, Portland keeps Sharpe, sends Jerami Grant to Toronto, and maybe has to sweeten the deal with a pick or another player, but that would be worth it. OG is one of the most versatile combo forwards in the game and could really give other teams fits in the biggest games.
- Portland drafted Cedric Coward at #11 in the 2025 NBA Draft and then traded him to Memphis for a future 1st-round pick and the #16 pick, which they used on Yang Hansen. But what if Portland instead stayed at #11 and took Carter Bryant?
(CM) Portland would probably be past the point of drafting rookies to help Dame at this point, and it’s more likely they wouldn’t have a high enough pick to get Bryant. But suppose they did, they would probably use it to help with rim protection and rebounding by taking a chance on center Derik Queen. Portland could also use this pick from the prior year in a trade with Minnesota to bring Karl-Anthony Towns to Portland. When the Knicks traded for KAT, Portland didn’t have the necessary assets or talent to draw KAT’s interest in approving a trade here. But with Lillard still here and a good roster around him, it would make sense that KAT is the missing piece. Portland would probably have traded their 2025 pick in the deal, along with a package of players, protecting Lillard, Hart, and OG, among others, but would have been willing to deal other players they felt were expendable. If Portland is drafting high enough in the first round of the 2025 draft, they either got lucky with a pick from another deal or had a bad season, making this timeline no less successful than the current one was. If they do have the #11 pick and need help on defense, Bryant would be a great addition to a championship team.
(BK) Ahead of the 2025 NBA Draft, I had my eyes on Carter Bryant for Portland. We knew he wasn’t a first, second or third option as a scorer, and his ceiling as a potential starter was in question. But that defense never was, and the thought of pairing him alongside Toumani Camara and Donovan Clingan in lineups was the stuff defense-minded coaches would dream of.
Of course, he alone would not make the Blazers any closer to contention. However, assuming some of the deals we’ve already talked about—either an OG or Bridges deal to play alongside Hart and Dame—have gone through, you’d be looking at a well-rounded rotation that balances offense and defense but prioritizes gritty, tough defenders to make life tough on opposing stars every single night.
- If you could alter only one timeline, would you rather have the #1 pick in the 2023 NBA Draft or the 1984 NBA Draft? The pick would be used on Hakeem Olajuwon in 1984 or Victor Wembanyama in 2023. You must pick one and only one.
(BK) As I mentioned above, the tough part in trading the No. 3 pick in 2023 for OG Anunoby is that you don’t know if it’s enough to sway Dame toward staying instead of demanding a trade. However, if you jump from No. 3 to No. 1—as the Blazers almost did, if not for one single ping-pong ball—you would have no fear that Lillard would stay to play with Wemby.
That’s how impactful everyone knew the rookie would be. And it’s beyond fun to think about how the last three years would have gone with Wembanyama in Rip City.
Of course, doing this means we pass on pairing Hakeem Olajuwon with Clyde Drexler in the mid-80s—not the mid-90s. Can you even imagine? It’s a lot of fun to think about.
Still, fully acknowledging recency bias, the chance to give Dame a real shot at winning a title in his prime is impossible to turn down.
Especially if you have Hart and OG Anunoby already on board.
A lineup of Lillard, Anunoby, Hart, Jerami Grant, Victor Wembanyama is crazzzyyyy. It might not be a title contender in Year 1, but three years down the road? I’d bet they’re fighting the OKC Thunder for Western Conference supremacy, just like the Spurs are today.
That’s worth the risk. And it’s worth gambling on Wemby over…dare I say it…Hakeem.
(CM) I think it would be amazing to see Wemby here, but I think Dame can win a title here without him, and we know Clyde Drexler was unable to win one without Hakeem, so let’s bring the Dream here both figuratively and literally. Hakeem and Clyde played together in college, narrowly missing out on a title. They spent a decade in the NBA playing against each other, then teamed up in 1995 to win a title, Hakeem’s second after winning the year prior. Drexler led the Blazers to two trips to the Finals with Kevin Duckworth as his center, and as much as I love Duck, Hakeem being here likely means the Blazers win one or both of those times. They might even have won in 1991, when they were the best team in the NBA, but lost in the conference finals to the Lakers. For all we know, Portland could win one, two, or maybe even three titles with Hakeem here. The Rockets were in the Finals in 1986; imagine what the Blazers could have done if they had Hakeem here during Clyde’s prime. Getting the Dream probably means no Buck Williams, as Sam Bowie is not here to trade away, but it’s possible the Blazers could still have brought Buck here and teamed him with Hakeem and Clyde. Kersey is likely still picked in 84, and I can still see the Blazers drafting Porter in 85, so you still get the majority of the original lineup plus Hakeem. Good luck against that team!
- If Wemby is in Portland in 2023, even if Lillard stays and gets hurt, you still have an insanely dangerous scorer and one of the best players on the planet. Suppose Lillard gets hurt and Wemby is not on the roster, who is the go-to player on this team and who would play center (assuming they don’t keep Jusuf Nurkic or D’Andre Ayton or have a pick high enough to draft Donovan Clingan).
(CM) KAT would be the center, and Portland should either sign or trade for Jonas Valanciunas or Robert Williams III to be his backup. This would provide Portland with two veteran centers who can play well at both ends and tend to be healthy when it matters most. Valanciunas had a decent career as a starter but still has some upside as a reserve. Williams III, we know, would work in Portland and was one of the best big men off the bench in 2026; imagine what he could do on an elite team. The go-to player would be OG; we know he can score in bunches when called upon and has the talent to be the primary option if there is not a guy like Lillard here. Nurkic is likely sent away in the KAT trade, and that means Ayton doesn’t land here at all, and Clingan would go to a team with a higher pick in the 2024 draft.
(BK) It’s tough for me to picture this scenario playing out with Nurkic sticking around. I don’t think the Blazers love him as a starting 5 at this point… but if you don’t trade Dame, the Ayton trade likely won’t go through, and I don’t know who else is interested in Nurk after his history of leg injuries.
So… I’ll cheat the rules and say Nurk is still my center. But I can live with that, considering I’ve kept Hart—a rebounding machine—and added either Bridges or, more likely, Anunoby, a defensive monster on the wing.
As a backup…I don’t know how I’d make it happen, but I’d get Steven Adams. The big man was traded in 2024 for Victor Oladipo—a former star at the end of his career—and three 2nd-round picks. Portland could beat that offer with a heavily protected 1st-rounder or a decent role player without an injury history.
This would be ideal. And it’d make Portland’s center position dangerous despite lacking star power.
- In 2022, Josh Hart was traded to Portland from New Orleans, along with Nickeil Alexander-Walker and a protected first-round pick (later used in the Jerami Grant trade), in exchange for CJ McCollum. Alexander-Walker was later dealt to the Jazz for two guys who didn’t pan out here. Would you rather keep CJ here and dump Hart (again), or keep Hart here and keep Alexander-Walker (who eventually had a breakout season playing alongside CJ in Atlanta)? Or keep the deals as is?
(BK) I’m keeping Hart here. With all respect in the world for CJ, he should’ve been traded even before this, and sending him out here means the Blazers get a stat-stuffing player in Josh Hart, who, I think, also fills the roster better.
Replacing CJ with NAW isn’t ideal. But also…what we now know about NAW tells us it’s WAY better for the Blazers today than we thought it was yesterday.
Hart and NAW on the same team in Portland? Count me in.
(CM) I would like to see Alexander Walker kept here and developed, but he would likely be dealt the following season as part of other deals or to get a future draft pick. We know he had a stellar season in Atlanta and can be a really good second option. Still, we can’t say for sure if he would have taken the big step here or just been sent for another project or to dump cash. If Grant can be brought here and then dealt to Toronto to get OG, then it all works for me. Portland got virtually nothing out of these deals, so they were not good in retrospect and didn’t look great at the time either. The pick in the Grant trade was on a player Portland wouldn’t have used or needed, so keeping the pick wouldn’t have made sense either. I vote to keep the deal as is and then trade Grant for OG.
Do the moves you made make you see the Blazers as a championship contender? If not, what additional moves do you need to see before they are ready to win it all (again)?
(CM) I really like this team built around Dame, Hart, OG, KAT, and Williams III, along with Holiday or Thybulle. They would need to round out the roster, but that wouldn’t be a problem as guys would want to come here and win a title with Dame seeing the team around him. They could use Queen or Bryant to help on the second unit and to keep teams honest when their best players are off the floor, but neither player is crucial to making this work. Portland missed out on a lot of good trades or free agents that likely would have been on the table if Dame had been here and had a really good team around him. It’s hard to get guys to come here for one superstar, but when you start to see other players taking a serious look at Portland, it starts a domino effect that could land a championship roster here. If they keep Dame and Hart and make good moves to get OG and KAT here, I love their chances in the playoffs.
(BK) I’m buying what my team is selling. In fact, here it is: Lillard, OG, Hart, Grant and Wemby (or Nurk/Adams, if we can’t get that No. 3 pick).
Even if we don’t get Wemby, that means Scoot is still on our bench blooming, and I can live with a two-timeline system in this scenario.
One piece we can’t bring along in this hypothetical is Jrue Holiday. And that is a bummer. His defense, playmaking, shooting, and veteran leadership would be hugely valuable on this roster.
But his absence is the price we pay for what I think is the best starting 5 in the NBA, as we’ve built it.
Do we win a championship? We can’t guarantee that. But do we compete in a way better than the Blazers currently built are today? You’d better believe it.
And that’s a lot of fun to think about.
Re-living the Blazers’ past is fun. And sometimes terrifying. But mostly, it’s a lot of fun to ask “What if?” even for your favorite team.
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