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Trail Blazers president of basketball operations joined the November 29 edition of CBS Sports' 'The Flagrant Two' podcast with Bill Reiter and Reid Forgrave. Among other topics, Olshey discusses his career evolution to becoming a general manager in the NBA, the impact former Trail Blazers' coach Mike Dunleavy had on his life, the challenges and opportunities that come with managing a roster in Portland, the mentalities of Damian Lillard and CJ McCollum and scouting for future prospects.

Listen to the full hour-long episode below. 

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AUDIO: Olshey Joins 'The Flagrant Two' Podcast

PORTLAND, Ore. (August 29, 2017) –The Portland Trail Blazers have announced a contract extension for President of Basketball Operations Neil Olshey, taking him through the 2020-21 season.  In keeping with team policy, financial terms were not disclosed.

“Neil has done an excellent job improving our team and getting us into the playoffs. With our young and improving roster, I expect our franchise to keep improving,” said Trail Blazers owner Paul Allen. “Continuity in the front office is important as we continue to grow, and this extension shows the confidence we have in Neil’s leadership.”

“I appreciate the confidence Paul Allen has in myself and the entire Basketball Operations staff,” said Olshey.  “I look forward to building on the foundation we have developed and the continued partnership with Bert Kolde, Chris McGowan, Terry Stotts and the entire Trail Blazers organization.  On a personal note, I’m very happy for my family as we’ve really embraced Oregon and the incredible spirit of Rip City.”

Promoted to President of Basketball Operations in 2015, Olshey was named the 10th General Manager in franchise history on June 4, 2012, and finished his fifth season at the helm in 2016-17. In his role, Olshey leads the organization’s Basketball Operations, overseeing talent evaluation, player personnel decisions, contract negotiations and salary cap management.

Less than a month after joining the Trail Blazers, Olshey drafted Damian Lillard (sixth overall), the fourth unanimous NBA Rookie of the Year in league history, and Meyers Leonard (11th overall). He then named veteran coach Terry Stotts head coach of the Trail Blazers on August 7, 2012.  Olshey also drafted and developed guard CJ McCollum (10th overall in 2013), winner of the 2015-16 NBA Most Improved Player award.

Last season, Olshey made a trade-deadline move to acquire center Jusuf Nurkic and a 2017 first-round draft pick from Denver in exchange for Mason Plumlee and cash considerations on February 13. That move ignited the Trail Blazers’ climb into the NBA Playoffs for the fourth consecutive season – even with the youngest roster in the NBA.

“Knowing Neil will continue to lead Basketball Operations well into the foreseeable future is a great thing for our franchise,” said Trail Blazers President and CEO Chris McGowan. “I am excited to continue our partnership in running this organization on and off the court with the goal of delivering a world-class experience for our fans.”

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Trail Blazers Sign President of Basketball Operations Neil Olshey to New Multi-Year Contract Extension

Casey Holdahl

ESPN's Zach Lowe, one of the best journalists covering the NBA, if not the best, posted a story today laying out almost the entirety of the Trail Blazers' offseason moves. Lowe seems somewhat optimistic about the deals Portland made this summer (though he notes they also have the potential to be "disastrous"), while stating the cold fact that a franchise which has shown no ability to draw big name free agents doesn't have a whole lot of options when trying to build a winner. It's easily the best retelling of the plan Neil Olshey executed this summer that you're going to find, so I recommend reading it from start to finish.

But let's pull look at some of the more interesting tidbits, of which there are many. First, the true target...

They chose the latter. Lowe points out that in order to keep any real cap space for next season, the Blazers would have had to part ways with many of the players from last year's team and delayed CJ McCollum's extension. And even then, it wouldn't be enough space to sign a max player, assuming one could be lured to Portland anyway, which has never been the case.

On the much-discussed topic of who plays what position, Lowe reports that Al-Farouq Aminu will start at power forward, a move that both Olshey and Terry Stotts have signaled this offseason, though he takes it one step further...

It's one thing to use Aminu at power forward for spurts, something the Trail Blazers did often last year, particularly late in the season, but another for him to play there "almost exclusively." According SportVU player tracking, as provided by Nylon Calculus, Aminu played 56 percent of his minutes at small forward last season while playing power forward 44 percent of the time. Granted, these numbers are imperfect, and positions in the NBA have never been more fluid, but going from roughly splitting time between small and power forward to playing almost entirely at the four is a fairly drastic change.

Then there's the topic of Dwight Howard, who the Trail Blazers were rumored to be pursuing during the July moratorium. According to Lowe, those rumors might have been a bit overblown...

This is just a guess, but this might be what Olshey was referring to when he mentioned "unfounded" speculation and that "a lot of names on lists that were never viable that we never had any interest in" during the press conference to introduce Festus Ezeli. Of course, there's no lack of speculation during free agency, so it could very well be in reference to someone else.

There's a whole lot more in there, particularly if you're interested in how Stotts might utilize Evan Turner, which is very much worth your time.

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Lowe: Blazers Wanted Whiteside, Aminu Will Start At Power Forward

Restricted free agency can be a bit tricky for both the players and teams involved. For the player, you sit through pitches laying out your value to another organization before entering into negotiations knowing full well that the whole exercise could end up being largely an act of futility. And for the team with the restricted free agent, they have to watch as one of their players is wooed by another organization whose contract offer they'll have to abide by if they want to retain the player. Things usually turn out fine in the end, but it can get a bit uncomfortable, especially if a player says he's excited to go to another team only to end up returning to his former team should they decide to match contract terms (as they almost always do).

But there's no rule stating restricted free agency has to play out that way. Teams don't typically mind restricted free agents getting offers from other teams, as it keeps them from being in the position of negotiating against themselves. But if there's a mutual desire to get a come to terms on a new contract without going through the dance of having a player get an offer sheet from another team first, teams are free to sign their own restricted free agents. Such was the case with the Trail Blazers and fourth-year power forward Meyers Leonard, who signed with Portland without ever getting an offer sheet.

"Obviously when it comes to free agency, you talk to other teams, you try to gain interest," said Leonard during a press conference at the Trail Blazers' practice facility in Tualatin. "But my main focus was to be back here in Portland. I spent all four years here, Neil (Olshey) has been the guy that’s backed me since the beginning. I truly believe watching him from the outside just as a player, he can understand talent, he can understand the future. I appreciate that he believes in me, I believe the coaching staff has a firm belief that I can really do a lot of good things, that I can continue to develop and become a much better player, which I know I will as well."

It's possible Leonard could have received a larger offer from another team had he expressed a sincere desire to leave Portland, just as it's possible the Trail Blazers could have tried to sign Leonard to a smaller contract with other teams neglecting to force their hand by not offering the 7-1 power forward an offer sheet. But even though the NBA, as the oft-repeated saying goes, is a business, it doesn't mean that decisions are always made with business solely in mind. There are relationships to consider, and if both parties wanted the partnership to continue, there's no reason for either side to engage in hardball tactics just to either save a few million (if you're the team) or make a couple million more (if you're the player). If the Trail Blazers are serious about signing players who want to be in Portland -- and all indications point to that -- they have to reciprocate that desire, which they did by signing Leonard to a four-year deal.

"Player retention is huge for us, it’s a big part of the organization having consistency and stability," said Trail Blazers President of Basketball Operations Neil Olshey. "Having Meyers, who was our first draft pick sign on long term is a great situation for us. We know he’s got a great future ahead, he’s going to continue to develop, he’s already contributed a lot to the organization. He’s a joy to have around here and for myself, Paul (Allen), Chris (McGowan), we’re all happy he’s going to be a part of the organization for the foreseeable future."

But while the team has shown they are invested in Leonard's future by signing him to a four-year deal, that doesn't mean he has been promised anything. Between the addition of free agent center Festus Ezeli, the likelihood that small forward Al-Farouq Aminu plays considerable minutes this season at the four and the continued development of 20 year-old power forward Noah Vonleh, the competition for playing time among Portland's bigs will be as fierce this season as it has been in years.

"It’s good to have a deep roster and I feel I bring something way different than the average player, the average big brings, obviously the main one being shooting, spacing the floor," said Leonard. "But I continue to develop on the defensive end with my rebounding, being more aggressive, understanding the game much better and just allowing the game to slow down. As you gain in game experience and you continue to develop chemistry within this group. This young group, obviously, we surprised a lot of people. You go from 26.5 games to getting to the playoffs, getting to the second round and as I sat there during the playoffs, it was hard for me. One, because when we were losing, I knew I could be helping. And when we won, I wanted to be a part of it. So there’s a hunger inside of me and I’m excited for what I can bring to this team."

That hunger will have to be satiated off the court for the next few months, as Leonard continues to rehab from a shoulder injury that cut his 2015-16 season short. But in the long term, he'll Leonard has the opportunity to prove the belief Olshey and Terry Stotts have shown in him during his career in Portland has been well placed, just as the team will have the chance to have a player with a unique skillset signed long term to to what could end up being an incredible bargain of a four-year deal.

"I have enjoyed all four years here so far," said Leonard. "It’s been a progression for sure. I come in as a 20 year-old, wide-eyed, not really know what’s going and now, all the sudden, I know that I’ve been a factor and I know I can play and now it’s really time to take that next step. I feel like I’m really getting there, not just with the shoulder — that was a bit of a setback — but throughout parts of last year, I could really feel myself starting to come into my own and really being more consistent... I’ve been here with Dame all four years, Allen (Crabbe), CJ (McCollum), all the young guys. Now that we add more and more pieces, I’m excited and I know I can really be a big piece to this puzzle, because again, this is going to be an exciting time for the Trail Blazers."

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Leonard, Trail Blazers Both Get What They Want With Four-Year Deal

Evan Turner, who the Trail Blazer signed as a free agent almost immediately after the expiration of the NBA's July moratorium, hasn't been in Oregon for long, but he already shares at least one concern familiar to many residing in the area.

"I know the real estate market is booming," said Turner during his introductory press conference at the team's practice facility in Tualatin. "I can afford it for sure but I don’t want to get duped, you know what I’m saying? If they don’t negotiate right, I just can’t move in."

If the luck he's had recently with negotiations holds up, Turner is going to be just fine when it comes to buying a house in his new home. But unlike Portland's housing market, which could only be described as heavily favoring sellers, it sounds like the hammering out of a new four-year deal reportedly worth $70 million between Turner, his agent Kevin Bradbury and Trail Blazers President of Basketball Operations Neil Olshey was much more collaborative. In the Trail Blazers, Turner found a young team on the rise where his skills and personality seem to be almost ideal fits.

"I think my skill set, I can play with the ball in my hands and off the ball, a lot of attention can be towards (Lillard and McCollum), as it should be, in regards to the defense and everything," said Turner who has averaged 10.7 points, 5.2 rebounds and 3.8 assists since being drafted with the second overall pick of the 2010 Draft. "I seen Chief (Aminu), he got freed up a lot. I like the bigs, how you have alley-oop options to them. I just thought the way they played is tough. They play with a lot of energy, a lot of toughness. They’re a top team and not only are they talented but they have a blue collar type identity."

And as for the Trail Blazers, they get a versatile, multi-positional player who can shore up their perimeter defense while unlocking the smaller lineups that Terry Stotts found success with during Portland's 44-win season, which culminated with a trip to the second round of the Western Conference playoffs.

"Watching video — it’s different during the process when you’re singling in on a guy and watching him versus preparing for the Celtics — he’s a really good facilitator, he’s a very good passer, a willing passer, I think his size helps him see things," said Trail Blazers head coach Terry Stotts. "One of the things that we wanted to do this year was to add another playmaker on the court. CJ and Dame had a lot of responsibility as far as being our playmakers, so we’re really counting on Evan to be a facilitator and playmaker for us, putting him in ball screens. He’s a very good, alert defender both on the ball and off the ball. He’s been a good teammate wherever he’s been, I think he fits into our culture and how we want to play, both on the ball and off the ball. He’s a very good rebounder for his position. Everything that we were looking for in that position, Evan fills it."

What's more, Turner fits the description of a player who wanted to come to Portland rather than simply settling for Portland, something that has been an important factor for Olshey in terms of player acquisition, which made for an easy negotiation.

"It’s been very important to us — in the last couple of years, we’ve talked about this — to have players that want to be here," said Olshey. "They believe in what we’re doing, they believe in this organization, they’re going to embrace the city of Portland, the fans and they’re willing to play the style of basketball we play. You can see just by sitting here what a high character guy Evan is. He’s an unselfish player, he’s versatile, he’s about making his teammates better and I think that’s going to be huge for us. I won’t go through where different guys were in the free agent process in terms of ranking, but the fact that we had a deal with Evan at 10 in the morning on July 1st probably tells you how highly coveted he was by us. We were aggressive in going after him, I didn’t want to get off the phone with his agent until we had a deal, it happened very quickly because we knew we had mutual interest."

While Turner fits well in terms of skills and age, one area of his game which is a bit incongruent with Portland's style of play is three-point shooting. Turner is just a 31 percent career three-point shooter and has failed to shoot better than 28 percent from deep in his last two season with the Boston Celtics, but he's hoping, as was the case with Trail Blazers forward Al-Farouq Aminu, that playing in Portland will help improve his accuracy through both practice and osmosis.

"The coach told me everybody shoot the three better when he get here, so I’m going to have to trust him on that," said a half-joking Turner. "And once again, just keep working each day on it. Most importantly, taking good shots and making the right plays and making the right read. That’s what I’m going to try my best to do and attempt to do."

As is the case with any free agent negotiation, money and years obviously played an important role in luring Turner to Portland, but the opportunity to have a more prominent role than he's had on any of his previous teams on a roster coming off consecutive playoff appearances and one of the most surprising seasons in recent history was, as the kids say these days, a major key.

"The money is great obviously, but the situation, I’m really excited about the situation," said Turner. "I’ve found a great fit to play with great players and a good coach and a great organization that has a great culture."

Now he just needs to find a great place to live at a reasonable price.

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Trail Blazers Find The Right Fit In Evan Turner, And Vice Versa

Everybody in the media wants a piece of the Trail Blazers. After starting out the season as an afterthought at best and a laughingstock at worst, the Trail Blazers, under the tutelage of Terry Stotts and the play of Damian Lillard and CJ McCollum, are one of the hottest teams and among the best stories in the NBA, the result of which has been a plethora of articles laying out how Portland went from replacing four of their five starters from last season to finding themselves in the middle of the Western Conference playoff race. It's well-deserved attention for the players and coaches who always believed they were far better than given credit for at the start of the season.

So here's a roundup of some of the recent Trail Blazers headlines. Most are from the last few days -- that's what happens when you're on a road trip that takes you through both Chicago and New York City -- and a few are a bit older, but all are still applicable.

• "Portland Speeds Up Rebuilding Plan," Zach Lowe, ESPN.com...

• "Untested Blazers Make Up For Youth With Plenty of Mettle," Steve Aschburner, NBA.com...

• "Damian Lillard Reshapes Surging Blazers In His Own Image," Jeremy Woo, SI.com...

• "All-Star snub fuels Damian Lillard, red-hot Portland Trail Blazers," Tim Bontemps, The Washington Post...

• "Young Blazers Following Damian Lillard's Lead to Surprising Heights," Kevin Arnovitz, ESPN.com...

• "Guard combo turns rebuild into playoff run in Portland," Ian Thomsen, NBA.com...

• "How Have The Blazers Been So Successful," SportsCenter...

• "Blaze On! Portland Isn't Going Away," Alex Wong, Sports On Earth...

• "We Have Never Seen Anything Like This Year's Portland Trail Blazers," Kevin Pelton, ESPN.com...

• "How the Trail Blazers Overcame The Loss Of LaMarcus Aldridge," Ken Berger, CBSSports.com...

• "Warning: Dangerous Rip Tip," Joel Gunderson, The Cauldron...

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Link Roundup: Blazers Dominate The Headlines As Hot Streak Continues

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Media Day 2015 Press Conference: Neil Olshey

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Trail Blazers President of Basketball Operations Neil Olshey was a guest on SiriusXM NBA Radio's NBA Today on Thursday. Hosts Brian Geltzeiler and Mike Dunleavy asked Olshey a variety of questions, mostly pertaining to the Trail Blazers' busy offseason. 

Check out a couple snippets from the show below. 

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Neil Olshey: "There's Nothing in Our Future but an Ascent"

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