Five Questions On Portland Trail Blazers Free Agency – Neil Olshey Shoots The Moon, Stuns NBA With Overnight Roster Overhaul

Following their most successful season in 19 years and fresh off a trip to the Western Conference Finals, Portland found themselves at a crossroads this offseason. With four key players needing new contracts, and the team holding limited funds in one of the deepest free agent pools in some time, the Trail Blazers held only a mid-level exception to re-sign one of their own players, or to sign a free agent. Most expected Portland to lose a couple of players, sign one or two, and head in to next season hoping for the best, while waiting for injured star center Jusuf Nurkic to return sometime in the second half of the season.

While addressing the media last Thursday, Blazers GM Neil Olshey discussed his free agent strategy, warning fans “don’t expect fireworks July 1st”. That statement (when taken out of context) led many to believe the team would be quiet this summer, as they did not have the available funds or trade assets to go after the biggest names.  What Olshey actually said was actually foreshadowing to what would take place in the coming days, as he found creative ways to swap expiring deals on players many fans felt needed a fresh start, and Olshey brought in fresh faces hoping to take the team to new heights, perhaps even their first NBA Finals appearance since in 28 years. And this was all accomplished without mortgaging their future or dealing core players.

With the draft and free agency mostly in the rearview mirror, Bryant Knox (BK) and Casey Mabbott (CM) discuss the Trail Blazers’ moves, Damian Lillard’s super max extension, how the new players will fit in, and how it will feel to see former Blazers in new uniforms next season. 

1.       Portland has been one of the most active teams in the offseason, what do you think of the team taking a more aggressive approach this summer?

(BK) Neil Olshey has made it clear that complacency is not an option—not after making the Western Conference Finals, and not with the Golden State Warriors running out a vastly different and diminished rotation going forward. In truth, nothing about Portland’s individual additions make the Blazers obvious title favorites. Hassan Whiteside isn’t Anthony Davis; Kent Bazemore won’t be Kevin Durant; Mario Hezonja obviously is not…actually, Super Mario might be Kawhi Leonard at this point. Seriously. But when stepping back and viewing everything through the prism of context, Portland’s GM has done two things that can’t be ignored: He’s re-carbonated a team that fell flat against the Dubs, and he’s improved areas of need that will make life easier on Damian Lillard and CJ McCollum. Olshey has pumped new life into a squad that already had momentum from the season, and that’s a trend Blazers fans have wanted to see for quite some time. 

(CM) I love it. I have not been shy about shouting negative reviews in regard to some of the moves Olshey has made in the past (the true mark of any established GM), but if you only grade his moves in the calendar year of 2019, it would be hard to give the guy anything but an “A”. He brought in Enes Kanter and Rodney Hood on “prove it” deals, and then re-signed Hood using the MLE. He traded the expiring deal of Evan Turner for the expiring contract of Kent Bazemore, then dealt the expiring contracts of Moe Harkless and Meyers Leonard for the expiring contract of Hassan Whiteside. He let Kanter, Seth Curry, and Al-Farouq Aminu depart in free ageny, and signed unproven wing Mario Hezonja. It remains to be seen what this new roster will be capable of, but it would be tough to say Olshey hasn’t given Portland every piece it needs given their limited assets, and if any of those players don’t work out, most are on one or two year deals anyway. 

2.       Damian Lillard agreed to a 4-year super max extension, with the deal making him the first player in NBA history to average $50M per season. How happy are you to see Lillard staying in Portland?

(BK) It takes a special kind of player to not only qualify for but truly earn a supermax. Damian Lillard is every bit the player and person you hope secures the big bag, and you know the league is thrilled that the deal likely aided in keeping a superstar on the small-market team that drafted him. Naysayers who point to Lillard’s age at the end of the deal aren’t entirely wrong, but it seems important to consider that the near-29-year-old’s game should age far more gracefully than many of his fellow point guards. He’s not the kind of 110 MPH player who relies on fierce athleticism and things like talking stuff both on and off the court instead of practicing his jumper rebounding. Of course, giving any player that kind of money is substantial and shouldn’t be taken lightly. But at the same time, if Olshey had gotten cheap or failed to convince a star player from a conference finals team to take nearly $200M, I think the city of Portland would’ve had a whole new kind of protest on its hands. 

(CM) Could not be happier. Lillard is an amazing player, and the best all-around player and off the court role model the team has had in quite some time. He’s up there with Clyde Drexler and Brandon Roy as the player current fans most identify with as their favorite Blazer ever. Will he win a title here? Maybe, maybe not. Not every all-time great wins a title. But he’s certainly won over our hearts with his play, his passion, and his shared love of this city with the fans. He’s worth every penny and more. 

3.       Al-Farouq Aminu, Evan Turner, Meyers Leonard, Moe Harkless, Seth Curry, and Enes Kanter will be in a different uniform next season. Does it sting to see so many familiar faces leaving the team?

(BK) At the risk of sounding cold, I haven’t felt connected to a player in a long time whose stage-left move invoked any sort of emotional response. Don’t quote me on that, of course, because the day Dame leaves you’ll find me sobbing in a corner checking my watch every .9 seconds waiting for Lillard Time. I will say, though, I wish Meyers Leonard had gotten a better rap in town over the past seven years. He didn’t do himself many favors with his inconsistent-at-best play, and his Twitter-blocking habits never helped public perception. But at the risk of diving too deep into the personal life of a guy I’ve never met and may never come across, those same characteristics can, and should, be viewed as someone cutting negativity out of his life and working through adversity to better himself, his mind and his production. That’s it. Forget the lottery selection and forget what you wanted him to be. Leonard’s work behind the scenes never surfaced to the level it maybe could have, but it did culminate in the performance of a lifetime in front of his home crowd during his ultimate if not unexpected swan song. That final act doesn’t erase a somewhat complex and messy story, but it was one I hope he and Blazers fans can hold onto as they go their separate ways or until they meet again. 

(CM) It always hurts to see former Blazers in new places, but you always wish them the best and look back fondly on their time in the Rose City. Aminu and Turner most likely wanted bigger deals than Portland was willing to give them given their limited impact, but I genuinely appreciate how much passion and effort they brought every single night. Curry and Kanter were amazing role players that deserved the shot to be starters somewhere else, and Harkless and Leonard were two guys I thought would have a larger share of the rotation this season, but were probably not going to start or be re-signed next summer as this team clearly saw them as role players, so it makes sense to see them go somewhere they have a shot to fight for a starting role. I’ll take the same stance I always do with departed players – I may not always root for them, but I won’t root against them. 

4.       The re-loaded rotation will feature new Trail Blazers Hassan Whiteside, Kent Bazemore, Nassir Little, and Mario Hezonja. What are your expectations for these players?

(BK) Entering the offseason, depth looked like a real concern with the realization that most if not all of Al-Farouq Aminu, Enes Kanter, Rodney Hood and Seth Curry could be gone, all on top of Nurkic’s absence. It wouldn’t be fair to say that the fear-and-loathing toward Olshey of years past re-surfaced, but there was an almost deflated energy around the fan base projecting that Portland’s GM didn’t have the resources to re-tool in a meaningful way on the fly. Needless to say, he’s proved everyone wrong in that sense. But what people should also keep in mind is that at times, this group is going to look energized, cohesive and downright dangerous, while other stretches will be sloppy, inconsistent and, at its worst, completely confusing. The good news is that I think the former proves the rule and the latter the exception. Lillard and McCollum need that to be the case, at least, if they’re going to have any fuel in the tank for another deep playoff run.  

(CM) Hoping for the best but bracing for the worst. I will give Olshey credit for taking low-risks and bringing in players on cheap or expiring deals, but that is a lot of new faces to break in all at once. The upside is that all of those guys need to treat this year as a “prove it” season, but they know they can just cut bait in the offseason and sign elsewhere if they don’t come to love the city of Portland. The flip side of that is also true, if Olshey and head coach Terry Stotts decide any of these guys are not good investments, they can just move on without having to find a trade partner or cutting someone and creating dead cap. You basically make this year’s roster a one to two year rental, and we’ll see where the dust settles. I’m hoping for big things from Whiteside and Bazemore, but will wait and see what we actually get from Little and Hezonja since they are simply unproven whereas Whiteside and Bazemore are proven vets that just need to gel with their new teammates. 

5.       What grade would you give Portland for offseason so far, and do you feel these moves can help Portland get to the NBA Finals?

(BK) New is always better. Or at least it can feel that way in the moment, which is why I’m incorporating an element of caution into my optimism and dropping the A that Neil Olshey probably deserves down to a B+. Despite the splashy feel to the move, Whiteside is more triple-to-right than home run, and it’s always possible the hype around Baze’s shooting ends up looking more like an indictment against his predecessor than a testament to his own touch. But in the interest of giving props where props are due, Olshey has done what needed to be done, and he’s accomplished it after years of largely deserved criticism coming from those who felt he must be more aggressive. Fewer than two days into July, he’s set the team up for continued immediate success. He’s retained his upcoming flexibility, if not improved it, by adding real-life expiring contracts that also double as desirable trade assets at the deadline. In the process, Neil found the best stop-gap 5 on the market to replace Nurk (and Kanter), and he did it without giving up a piece of his core. As GM—and this may truly go down as his greatest accomplishment when we look back on this whole era 10, 15, 50 years from now—Olshey has literally kept Lillard out of the KD/Kyrie/Kawhi category of city-spurners and set the path for The Letter O to end his career right where it began. Part of that is Rip City, part of it is Dame’s personal values, but a monumental, criminally underrated part is Olshey and how he’s handled his relationship with Lillard and his construction of the roster. Ya know, the more I think about it, as unlikely as it seemed after the 4-0 WCF sweep, the Blazers are bringing a better team into 2018-19 than the one that left the playoffs, and the future, while fluid as today’s rumor cycle itself, presents an intriguing, albeit foggy fork in the road instead of a dead end. With the Warriors a sudden enigma, it really is anyone’s time to strike. I don’t know if I’d go as bold as to name Portland the 2020 champs, but that B+ is officially back to A. It’s a great summer to be a Blazer. 

(CM) Olshey did an outstanding job, I’m giving him a solid “A”. I really thought the Blazers were going in to next season with a starting five of Lillard, CJ McCollum, Harkless, Aminu, and Collins, with very little depth and no money to round out the rotation. I fully expected them to make some insane deal at the trade deadline to get back on track, and we would look back on the 2018-19 season as when Lillard’s career peaked given the supporting cast around him. Now we get to go in to next season with actual optimism, and with the West blowing up and so many teams breaking in new lineups, I fully expect Portland to be a contender for the 2020 NBA title. 

About Casey Mabbott 214 Articles
Casey Mabbott is a writer and podcast host born and raised in West Philadelphia where he spent most of his days on the basketball court perfecting his million dollar jumpshot. Wait, no, that’s all wrong. Casey has spent his entire life here in the Pacific NorthWest other than his one year stint as mayor of Hill Valley in an alternate reality 1985. He’s never been to Philadelphia, and his closest friends will tell you that his jumpshot is the farthest thing from being worth a million bucks. Casey enjoys all sports and covering them with written words or spoken rants. He has made an art of movie references, and is a devout follower of 80's movies and music. I don't know why you would to, but you can probably find him on the street corner waiting for the trolley to take him to the stadium or his favorite pub, where he will be telling people the answers to questions they don’t remember asking. And it only goes downhill from there if he drinks. He’s a real treat.