The morning of July 1st was when it all changed. I was eating my breakfast in peace when Cole, a co-founder of Rip City Rundown and my brother, dropped the news that none of us wanted to hear: Damian Lillard had requested a trade. I immediately spit out my bagel and my mind started racing with so many thoughts. What does this mean for the Blazers? Is Jody going to sell the team now? Why would Dame do that? But at the same time, why wouldn’t he do that? After all, our organization is incapable of putting talent around Lillard. As much as Joe Cronin won’t admit it, Lillard’s trade request was two years in the making. Ever since Neil Olshey was fired in 2021, Joe Cronin and Blazer management have been sneakily tanking in order to accumulate young assets.
The next few hours following the trade request were full of all kinds of emotions. We coped and reflected. It seemed like we went through every emotion possible. We watched old Lillard highlights and reminisced about the golden years of the Lillard era. We took turns bashing Cronin and Jody Allen for their perceived incompetency. Cole and I made a video that was full of sharp comments directed toward Cronin and Jody Allen, which were warranted I might add. We were joined by Cody for our full-length podcast the next day, and he brought up an incredible point that put Jody Allen’s decisions into perspective. He said that if Jody Allen had $2,000 of total money, she would need to spend $5 to dip into the luxury tax and pay up to surround Lillard with talent. Jody can spend the Allen’s money the way she wants to at the end of the day, but Cody’s analogy portrayed the cheapness of Jody Allen recently. Following the podcast, Cole, Cody, and I really contemplated the future of this channel. After all, we started it in 2021 during the playoff series against the Nuggets. As you all know, the Blazers have been horrible ever since then: two seasons of injuries, stars sitting, and missed playoffs. Since the inception of the channel, Portland has been terrible, and we have been craving some success for the Blazers to go along with our channel. We wanted to talk about a contending team for once. With Lillard asking out, it seemed like a long, long time before Portland would be good again. But it doesn’t matter at the end of the day because we realized we would be Blazer fans no matter who wears that jersey. It is team over player at the end of the day. As much as we love Dame, we are ecstatic to see this team forge their own path and go through the gauntlet that is the journey to an NBA title.
On a recent podcast, we argued if Portland has a better chance to win a ring with Dame at the helm or by rebuilding. There’s a fascinating case for both sides. Lillard is the best player Portland has arguably ever rostered and bringing a second star in would give the Blazers a real, real chance. But would they be better than Denver? Milwaukee? Phoenix? The number of contenders would make it really difficult for Portland to truly make a run. On the other hand, rebuilding would give Portland fresh hope and young stars and assets to hopefully turn into something one day. But the issue with rebuilding is youth and flawless execution by the front office. In a rebuild, nothing is guaranteed. Players could get injured, bust, or be signed to horrible contracts. If you want a brutally honest answer, Portland probably won’t win a title in either scenario. As a small market team, it is near impossible to build a championship team. It requires excellent drafting, smart signings, the perfect timing on a big swing in a trade, and most importantly, commitment to a plan. Think of it like building a house brick by brick except the Blazers are using sticks. The big market teams get to use bricks: they have the city, the pedigree, and the history to fall back on if they fail once or twice. Small market teams have to use sticks to build their house; it requires precise planning and incredible detail. One bad move or bad signing to wreck the whole building process. Each stick must be placed at the perfect time in the perfect order with the correct plan in mind. And that was Portland’s issue. Portland was never committed to a plan; they vowed to thread the needle of two timelines with Dame. Well newsflash: that’s basically impossible. So what happened? Cronin didn’t swing in a trade and didn’t mortgage the future of the franchise for Dame. It sucks.
The silver lining that will come out of this summer is Portland has finally 100% committed to something at least, which can only help the health of the franchise. Do I wish we chose Dame over a rebuild? Absolutely. But I also acknowledge that Portland is probably better served starting fresh and jumpstarting the rebuild with the return from a Lillard trade. But that’s the kicker - this Dame trade that Cronin pilots must be executed to perfection. And can we really trust in Joe Cronin to pull off one of the biggest trades in franchise history? Does Cronin have it in him? For better or for worse, Cronin’s stint in Portland will be defined by this trade. If he hits a home run, then Portland will have checked a major box off. If he doesn’t pull it off, the house of sticks could come crashing down at any moment. Cronin must give this young group a chance in 3-5 years – getting a star return in the Lillard trade is a huge step in that.
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After the dust had settled and Summer League began, Rip City Rundown is in a good place. We are pumped to make content for you, and we are eager to grow this channel and brand alongside this team. We love Damian Lillard, but we also know how much potential this young group has, and we are excited to watch these baby Blazers grow up. As soon as Scoot stepped on the floor against the Rockets, we knew everything would be alright. Players will come and go, but that jersey will always be there. It is always team over player, even if that player is one of the most special players to ever step foot on the Moda Center floor. And who knows? Maybe one day Dame will make his return to Portland and do what Lebron did:
“Portlanddddd, this is for you!”
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