Damian Lillard has officially requested a trade. The Portland Trail Blazers, the organization which drafted him 6th overall, out of Weber State, in 2012, are now at a defining moment in their franchise history. His demand comes on the heels of Blazers GM Joe Cronin opting to draft G-League Ignite Guard Scoot Henderson, with the 3rd overall pick in the 2023 NBA Draft, instead of moving the pick for a veteran player, which Dame had asked the front office to do leading up to the draft. Prior to his estrangement, Damian Lillard had been extremely public about his desire to stay loyal to the Blazers, even going as far as saying he had “too much pride for that or be too much of a competitor where I couldn’t bring myself to do it, but it also makes it more fun. You get to take a monster down and that’s always fun,” when asked about the idea of him joining up with another star or two to form a “superteam” to defeat the Golden State Warriors. A lack of playoff prosperity, over several seasons, caused a now 33-year-old Dame to reconsider his options as he heads into the twilight his career.

Over Damian Lillard’s 11-year tenure as a Blazer, they made the playoffs 8 out of 11 seasons. Digging deeper there are plenty of regular season victories, but not many playoff series’ wins. 5 of the 8 playoff trips ended after round 1, with only 1 Western Conference Finals appearance, a 4-0 sweep by the Golden State Warriors in 2018/2019. A player like Dame wants, at minimum, an NBA Finals appearance, if not a ring to truly cement his legacy as a top-75 guy. That goal was going to go unrealized in Portland. Unfortunately, the front-office wasn’t able to figure out the right head coach / mixture of players to maximize the slick-dribbling, high-scoring, time-telling, 7x All-NBA Guard.

It’s time for the Portland Trail Blazers to move on from their best or 2nd best, depending on who you talk to, player in franchise history. Normally, a player of Damian Lillard’s stature would fetch a return similar to what Utah received for Rudy Gobert, the compensation Oklahoma City recouped for Paul George, or the haul Brooklyn accepted for Kevin Durant. Basically, the maximum amount of unprotected 1st round picks (3-5), a prospect or two, and a couple of players to make the salaries match. But Dame specifically seeking a trade to the Miami Heat throws a gigantic wrench into the trade equation.

Joe Cronin has the unenviable task of trading their franchise superstar in a depressed market. Typically, the whole league would be calling and offering their best package for Dame, but since the Heat have been publicly named, and reports indicate he wouldn’t show up to training camp if sent to another team, it’s going to be very tough for Portland to extract full value for the player. Another issue is Lillard’s extraordinary expensive contract.

Per Spotrac, Damian Lillard will earn $45,640,084 in 2023/2024, $48,787,676 in 24/25, $58,545,211 in 25/26 and $63,228,828 in 26/27 for a guaranteed total of $216,201,799 dollars across the next 4 seasons. Not many teams in the NBA can create or have the available cap space to absorb a contract that pricy while continuing to field a championship-level roster. Dame recently turned 33-years-old. He keeps himself in phenomenal shape, has a relatively injury-free history, and shooting is a skill that ages well, so concerns about his longevity or underperformance aren’t too worrisome.

The Miami Heat start the Damian Lillard negotiations miles ahead of the other franchises. If they offer enough Dame will be a new South Beach resident. Although, Miami should be apprehensive in giving up so many future assets, picks & prospects, to lock themselves into a trio of Dame, Jimmy Butler, and Bam Adebayo for the foreseeable future, which in 2023/24 alone costs around $122 million dollars. Spending that kind of money on 3 All-NBA players can work, but it really hampers Miami Heat GM Andy Elisburg’s ability to build out the rest of the roster as teams now have to spend between $136 million dollars (salary cap) and $165 million dollars (Luxury Tax Level) for the upcoming season. A team can spend more than the $165 million dollars (up to $185.2 million dollars), but at a steep cost including tighter trade restrictions, inability to sign expensive buy-out players, and a chance to lose out on a high draft pick due to the clause: A team’s first-round pick is moved to the end of the first round if they remain in the second apron for three out of five seasons. Yes, the Heat are notorious for attracting veteran players on the cheap and uncovering/developing undrafted players, but they must win now for any Dame trade to be deemed a success.

Enough backstory, let’s get to some trades!

Tyler Herro as the centerpiece of any Damian Lillard trade isn’t ideal for Portland due to their depth at the position (Shaedon Sharpe, Anfernee Simons), but he is a coveted shooter and 20 PPG scorer who could be flipped individually or as part of an expanded 3 or 4-team trade. The issue being he’s owed $120 million dollars over the next 4 season, so Portland would be taking on quite a bit of money when they’re, potentially, looking to go young and cheap over the next couple of seasons. Duncan Robinson is a solid 3-pt shooter (.399% career average) with some size, but his contract is a headache. He’s collecting $18,154,000, $19,406,000 and holds a player option for $19,888,000 over the next 3 seasons. That’s entirely too much to pay for a career 11.1 PPG player. Nikola Jovic is a 6-ft, 10-in 20-year old Serbian with 204 minutes of NBA experience. A highly raw, but intriguing prospect who needs a couple of seasons of steady development and gametime to mature. As far as draft compensation goes 4 unprotected 1st round picks seems fair.

A lot of the same misgivings over the previous deal are also involved here; Tyler Herro’s redundant skillset along with his and Duncan Robinson’s contracts. One major difference is Portland gets out of Jusuf Nurkic’s money. His age doesn’t align with the timeline of Portland’s nucleus. He can’t stay healthy, isn’t very mobile, and won’t open up driving lanes for Scoot Henderson or Shaedon Sharpe. Plainly said, its hard to find a place for him in the modern NBA. It would be wise of Joe Cronin to move him in any Dame deal. Nassir Little gets thrown in as salary filler. He’s a solid role player who’ll add some shooting, rebounding, and defense to a team fighting for a championship. Kyle Lowry’s $29.6 million dollar expiring contract is appealing, and he could, theoretically, mentor Scoot, but his minutes played would be pretty low.

If Damian Lillard wants the sun, fun & beach of Florida yet Portland can’t reach an agreement with the Heat, and the market opens up, Orlando should call Joe Cronin with an offer. Former NBA player Anthony Parker recently stepped in the role of Magic GM and making a move for Damian Lillard would be one way to make a splash. He can’t offer much more than expiring contracts and a host of draft picks, so maybe the Trail Blazers wouldn’t value their offer as highly as one with a prospect or two. The idea of Dame stabilizing a young, on-the-cusp-of-the-playoffs Magic team led by reigning Rookie of the Year Paolo Banchero and versatile point forward Franz Wagner is very enticing. This franchise has been searching for a true PG for many seasons with no luck, trading for Dame would rectify that oversight immediately. On the other hand, the Blazers getting Markelle Fultz’s and Gary Harris’s expiring contracts, around $30 million dollars in space, Jon Isaac’s tantalizing yet oft injured potential, and five 1st round picks doesn’t exactly move the needle.

The Philadelphia 76ers President of Basketball Operations Daryl Morey and GM Elton Brand have a James Harden-sized problem on their hands after he picked up his 2023/24 player option for $35,640,000 and then immediately asked for a trade, with his preferred destination being the Los Angeles Clippers. Joel Embiid said he wants to win a championship in Philly, or wherever. This statement alone should put Morey on high-alert, as the reigning MVP might be the next megastar to agitate for a trade. What better way to appease him then adding a Point Guard who’ll get him the ball where/how he likes it, while keeping the floor evenly spaced and double-teams off the big guys’ back. Portland recoups by acquiring Tyrese Maxey, though he’s a little redundant with Scoot Henderson and Anfernee Simons on the roster, Tobias Harris’s $40 million dollar expiring contract, and three 1st round picks. Flipping Maxey is complicated because of him being on a rookie scale contract, and in any trade a team may only take back between 175%-200% of the outgoing money. Meaning if the Blazers wanted to trade Maxey they’d only be allowed to take back a player who made up to $8.5 million dollars, unless they signed him to a lucrative contract extension, which would tie up their cap space.

Victor Wembanyama is the most hyped NBA prospect since LeBron James. He’s a 7-ft, 6-in 18-year-old Frenchman, who moves like a guard and has a dribble package to go with, can shoot over anyone and from anywhere on the court, is an unselfish passer, and has the length and intelligence to anchor a defense. He’s one of those create-a-players, with the stats turned up, come to life. The perfect prospect. Smart money says San Antonio will take the slow approach and take their time building around him.

Let’s pretend they want to accelerate their timeline, why wouldn’t 74-year-old Gregg Popovich and San Antonio want to add a top-tier PG, who’ll take a massive amount of pressure off the rookie sensation and ease his transition into the NBA? Wembanyama’s been pictured with Tim Duncan, David Robinson, and Manu Ginóbili since being drafted, so a veteran support system is already forming around him. An active player, with the resume and influence of Dame, would further solidify the veteran presence around him. How unstoppable would a Dame-Wemby pick-and-roll be? Devin Vassell is a highly underrated SF/SG who’s improved every season in the NBA (5.5 PPG –> 12.3 PPG –> 18.5 PPG) and his shooting fits next to Scoot and Shaedon. He’ll need an extension, though. Doug McDermott can be a decent rotation guy for Portland. He’s shooting will help space the court. Devonte’ Graham is a tougher sell due to his remaining contract and positional overlap. He’d be a buy-out candidate for sure. Four 1st rounders sweetens the deal for Portland. The Spurs don’t know how best to use/build around Wembanyama, so it would be unwise of them to get over their skis and mortgage their future.

**With the introduction of a 3rd team, the trades are about to jump up a level in complexity and creativity.

This one is next to impossible, as there’s a 0.0000001% chance the San Antonio Spurs trade Victor Wembanyama before he ever steps foot onto the court for them, but let’s have a little fun. Joel Embiid’s the reigning MVP and desperate to win a championship. It also seems like his days in Philadelphia are numbered. Him joining forces with another star like Damian Lillard, under the tutelage of Gregg Popovich, is a fascinating prospect. San Antonio would have to pay a steep price, both dollar and player-wise, to acquire the disgruntled duo. Daryl Morey would be over the moon receiving Wemby, Keldon Johnson and Sidy Cissoko for Embiid. An unbelievable return for the testy big man and a very quick roster overhaul. Maybe James Harden could even be enticed back into the fold by the appeal of playing with the young French prospect…sike! Portland picks up valuable draft capital across multiple years (CHA ’24 pick could end up no. 1 overall), as well as a couple of solid young players with potential in Devin Vassell and Jeremy Sochan.

Last season, Tyrese Haliburton made his first All-Star team after averaging 20.7 PPG & 10.4 APG and was rewarded with a 5-year, $205 million dollar max extension by the Indiana Pacers. Now’s the time to find him a long-term back-court partner of similar age who compliments his style. Buddy Hield can’t be that player since he’s going to be 31 in December. On the other hand, Tyler Herro is literally a month older than Haliburton and locked into a 4-year contract giving head coach Rick Carlisle plenty of time to develop the chemistry and optimize their talents. Add in 1st team All-Rookie Bennedict Mathurin, a player who’ll keep improving, Myles Turner, a stretch-5 who protects the rim, and the alluringly athletic Power Forward duo of Obi Toppin and Jarace Walker to the mix, and they’ll have a very good chance at making the playoffs. Portland is able to flip Herro for Buddy Hield’s expiring and Andrew Nembhard, asking for a pick from Indiana isn’t out of the question either. Kyle Lowry’s expiring contract helps the Blazers free up some money while being a veteran presence for Scoot to learn from would be worth trading for, plus it’s only for a season and Joe Cronin could opt to buy him out if things don’t work out.

This would be ironic after Dame hit the walk-off shot over Paul George in the playoffs to send the Oklahoma City Thunder home. Similar to San Antonio trading for Damian Lillard, the Thunder don’t want to get ahead of themselves before seeing how the homegrown talent meshes together. Plus, OKC isn’t exactly a destination for megastars with mega-personalities, but its a fun exercise nonetheless.

Sam Presti and the Thunder have a treasure trove of draft picks and high-level prospects to dangle in any trade talks, affording them the ability to enter any discussions for any dissatisfied star at any time. In this instance, surprisingly, OKC don’t need to send out of any their own draft picks, only picks they’ve acquired along the way. A lot of auspicious young talent will be leaving, but for a tandem of Dame and Joel it’s potentially worth it. Having those two players vault any team into NBA title contention immediately. The problem might be getting those two megastars to buy into an extraordinarily small market in Oklahoma City. Philadelphia ending up with Shai Gilgeous-Alexander and Lu Dort might not be optimal as long as James Harden and Tyrese Maxey are still on the roster. If the latter two are traded for wing or center help, then the deal makes more sense. Portland comes away with some incredible pieces to put next to Scoot and Shaedon. Chet Holmgren has remarkable length, significant shooting upside and has potential to develop into something wholly unique and unseen in the right conditions. The downside being his thin frame (7-ft, 195lbs) and recent injury history. He missed his rookie season due to a Lisfranc injury sustained at Jamal Crawford’s ProAm in Seattle, WA. Josh Giddey has good size, can attack downhill and initiate the offense. Outside of Walker Kessler, Jalen Williams might’ve been the revelation of the 2022 draft. He’s an outstanding athlete, who can finish in traffic over and around most players, has quick hands that led to 103 steals his rookie season and his shooting splits are promising (.521% / .356% / 812%). Ousmane Dieng is similar to Nikola Jovic, a highly raw but intriguing prospect with size and ability, who needs a couple of seasons of steady development and gametime to mature. A lineup of Scoot-Shaedon-Chet-Jalen-Giddey would pass, cut and outrun most teams. Those players have the ability to form a varied and exciting young core.

Ben Simmons desperately needs to get out of the spotlight. What better place than Portland? In a place where there aren’t any expectations maybe he can respark his love and commitment to the game. Otherwise, his deal expires after the 2024/2025 season, which isn’t too far into the future, maybe by then Scoot Henderson will have matured into an All-Star and other players will want to sign via free agency with the Trail Blazers. Nic Claxton is a useful big who defends and rebounds, a team can’t have too many of those guys, and plenty of draft picks too. Keeping Anthony Edwards, Karl-Anthony Towns and Rudy Gobert together for another season seems like a disaster. In an ideal world, Gobert is the one moving on, even with the optics looking as bad as they would. Instead, KAT moves East linking up with Mikael Bridges. Town’s contract extension, which starts in 24/25, is absolutely massive, 4-years for $222 million dollars. It’s a ton of money for the Nets to be taking on. But since they don’t own their own picks in ’24 and ’26, traded to Houston in the James Harden deal, tanking isn’t really an option unless they think Phoenix will massively underperform, implode and those picks end up in the lottery. Fielding a playoff-worthy team is the best way forward for Brooklyn. Minnesota solves their big man problem while acquiring Tyler Herro to become the back-court partner of Anthony Edwards. They too owe their short/medium term draft capital to another team, so no point to bottoming out.

The Houston Rockets appear to want to win now. Over the off-season, they hired Ime Udoka, who led the Boston Celtics to the 2022 NBA Finals in his rookie season before being suspended, and eventually, dismissed for an improper relationship with a staff member. The Rockets also spent $264,886,460 million dollars on Fred VanVleet, Dillion Brooks, Jock Landale, Jeff Green and Aaron Holiday in free agency. Jalen Green and Kevin Porter Jr. aren’t bad or unimportant players, it’s just being involved in a losing culture like Houston have amplified their bad habits. Shot selection and defensive concentration are a couple that spring to mind. Resetting the team standards start with Ime Udoka, but he also needs the players to buy-in. Getting a guy like Tyler Herro, who’s only ever been around a strong, winning organization like Miami, is another way to help turnaround the Rockets locker-room. Losing Tari Eason hurts, although Jabari Smith Jr. is a bigger, better, more talented version. Charlotte are in the midst of an ownership change, and haven’t made the playoffs since 2015/2016, so breaking this unwanted streak should be new ownerships’ top priority. Taking on money may not be what the new group is interested in, so throwing in a couple of picks is a necessary sweetener. Kevin Porter Jr. brings his offense first game to a Charlotte team crying out for a scorer. They finished 27th in the league in scoring last season after averaging 111 PPG. Portland gets some draft capital, Gordon Hayward’s expiring contract and a couple of good, young prospects, especially Jalen Green. The paring of him and Scoot Henderson might break the rim with all the driving and dunking. The problem being this is a smaller guard combination, which makes it a similar issue to when Portland employed a Dame/CJ back-court.

Damian Lillard deserves to be traded to a place where he can legitimately compete for an NBA championship. It’s the least the Blazers and Joe Cronin can do for Dame after his many years of service to the franchise. Miami is the preferred destination but the assets they have available don’t quite match with what Portland wants, which is young players in the front-court (Center or Forward) to build around Scoot Henderson & Shaedon Sharpe and draft capital to use or enter the trade market for an unhappy superstar. The market still has a chance to open up to other teams, either as a primary trade partner or as a 3rd or 4th party. Joe Cronin will have options and doesn’t need to rush the trade process. Although, he shouldn’t start the new season with a disgruntled player like Lillard on the roster. What isn’t so clear is the roadmap Portland should follow to build around and maximize Scoot & Sharpe. It’s tough because Henderson hasn’t played in an NBA game yet, while Shaedon was finally given free reign to experiment as the primary ball handler very late into his rookie season and neither have played a single minute together. Their potential union is wholly unknown. GM Joe Cronin and head coach Chauncey Billups have no idea what their ceiling is or what types of players most complimentary Scoot and Shaedon.