It finally happened. After 11 seasons, seven All-Star Games, seven All-NBA selections, a franchise scoring record, a pair of series-ending shots, a 71-point game, a summer of trade rumors, and over a decade's worth of memories... Damian Lillard is no longer a Portland Trail Blazer.
On September 27th, the Blazers finalized a three-team deal with the Milwaukee Bucks and Phoenix Suns that resulted in Lillard heading to Milwaukee. Portland got Jrue Holiday, Deandre Ayton, Toumani Carara, a 2029 Bucks’ first-round pick, and pick swaps in 2028 and 2030. The Suns received Jusuf Nurkic, Nassir Little, Keon Johnson, and Grayson Allen. Holiday was later repackaged to the Boston Celtics for Robert Williams, Malcolm Brogdon, and two first-round picks.
Lillard has been overlooked his entire life. He was overlooked coming out of Oakland High School, ranked outside the top 200 players in the 2008 recruiting class. He was overlooked in the NBA draft, falling to the Trail Blazers at pick number six. And he was overlooked when he wasn’t selected as a Western Conference All-Star in 2016 and 2017. But every time he’s been overlooked, he has always proved his doubters wrong. When he was doubted as a recruit, he became a two-time Big Sky Player of the Year for Weber State. When he was doubted in the draft, he won the Rookie of the Year award. When he was doubted as an All-Star in back-to-back seasons, he made the All-NBA First Team the next year.
During his time in Portland, Lillard went from an undersized guard from a small school to a franchise icon and unquestioned future Hall of Famer. He constantly carried undermanned Blazers teams to heights they shouldn’t have been able to reach. When he walked off the Houston Rockets with a series-winning buzzer-beater in the first round of the 2014 playoffs, he showed the potential for greatness, but when he did it again to the Oklahoma City Thunder in 2019, he cemented himself with Bill Walton and Clyde Drexler as one of the greatest players in the history of Rip City basketball.
In 11 years with the franchise, Lillard only ever played with one other player who was selected to an All-Star team, LaMarcus Aldridge, who was an All-Star in Lillard’s first three seasons in the league. After Neil Olshey selected Lillard and C.J. McCollum in his first two years as General Manager, the only other impactful draft pick he made was Anfernee Simons, another small guard whose best days as a Blazer will come without Lillard on the team.
When he was drafted, Lillard came to a team built around a core of Aldridge, Wesley Matthews, and Nicolas Batum. With the additions of Lillard and center, Robin Lopez, who was acquired in a trade ahead of the 2013 season, the Blazers were able to build a starting lineup that took them to back-to-back playoff appearances and, with the help of Lillard’s heroics, advanced them past the first round for the first time in 14 years. But after the 2015 season, Aldridge, Matthews, and Lopez left in free agency, and Batum was traded for Gerald Henderson and Noah Vonleh, leaving Lillard with a brand new starting lineup.
Despite a depleted roster, Lillard stepped up again to lead Portland to the playoffs, raising his scoring average from 21 to over 25 points per game while being named to the All-NBA Second Team. The only help he received was from McCollum, who in his third season in the league, and his first as a starter, broke out to win the Most Improved Player Award while scoring over 20 points per game. Together, the backcourt duo was able to lead the Blazers past the Los Angeles Clippers in the first round but were ultimately well outmatched by a Golden State Warriors team that was coming off of a record-setting 73-9 season.
Over the next five years, Lillard took his game to another level, making four All-Star and All-NBA teams, including a first-team selection in 2018, while averaging over 27 ppg. Along with McCollum, the Robin to his Batman, who averaged over 22 points of his own, Lillard led the Blazers to five straight playoff appearances. But despite the regular season success that generated those playoff appearances, it wasn’t able to translate into wins once they reached the postseason. With the exception of a run to the 2019 Western Conference Finals, on the back of Lillard’s series-ender against Oklahoma City in the first round and McCollum’s 37-point game seven to beat the Denver Nuggets in the second round, Portland never made it past the first round.
The Lillard-McCollum-led teams were constantly limited by the fact that they were starting two guards under 6’3”, which significantly limited them defensively. This, paired with centers like Mason Plumlee, Jusuf Nurkic, Enes Kanter, and Hassan Whiteside, all of whom struggled to guard in space against the pick and roll left them with a defensive rating below league average in all but one year. Even in 2019, the year they made their deepest playoff run since 2000, they were swept in a relatively uncompetitive series by a Warriors team that was missing Kevin Durant.
During the entire Dame and C.J. era in Portland, they were never given a fair chance to win by their front office. When constructing a team built around two undersized, offensive-minded guards, a front office should try to surround them with a mobile center who can protect the rim while guarding the pick-and-roll, and big wings who can guard ball-handlers at the point of attack. Instead, the Blazers chose players like Nurkic, Al-Farouq Aminu, and a 35-year old Carmelo Anthony, leaving them well behind other Western Conference contenders. The final move Portland made to try to save the Lillard-McCollum combo was to trade Gary Trent Jr., a 22-year-old wing averaging a career-high 15 ppg while shooting over 39% from three-point range, for Norman Powell, another 6’3” guard that the Blazers tried to play on the wing, which obviously didn’t work defensively with the roster they had already constructed.
After another first-round exit, despite a historic performance from Lillard, the Blazers decided to part ways with Head Coach, Terry Stotts, the second-most winning coach in franchise history, after 9 years with the team. In his place, they brought in former NBA champion, Chauncey Billups, who had served as an assistant coach for the Los Angeles Clippers the year prior.
With him, Billups brought a new defensive scheme that emphasized blitzing the ball-handler when guarding the pick and roll instead of playing the traditional drop coverage that Stotts had typically played. The idea behind this was to prevent ball handlers from getting into easy pull-up mid-range jumpers against a dropping Nurkic. But what Billups didn’t account for was the fact that, since Nurkic had snapped his leg in half near the end of the 2019 season, he had been one of the least mobile centers in the league. Putting him up near the level of the screen meant that there was no one to protect the rim as he was far too slow to get back into the play, constantly putting Portland in two-on-one situations they would lose every time. In Stotts’ dropping scheme, Nurkic had always averaged over a block per game. Even though he wasn’t extremely mobile, he was big enough to offer some sort of deterrence at the rim. But with Billups’ blitz, he dropped down to just 0.7 bpg, as his lack of mobility, and with it, the Blazers' lack of rim protection were both exposed.
The 2022 season saw both Lillard go down with the first major injury of his career, as well as the end of the Dame and C.J. era in Portland. Lillard had been dealing with an abdomen injury all season. He played his last game of the year on December 31st, undergoing surgery in January that ended his season after only 29 games. With the Blazers out of contention with a 21-33 record, they decided to flip McCollum along with Larry Nance Jr. and Tony Snell to the New Orleans Pelicans ahead of the trade deadline for a package that included Josh Hart, Nickeil Alexander-Walker, Tomáš Satoranský, Didi Louzada, a protected first-round pick in that year's draft, and a future second-round pick swap.
From that trade, only Hart would make a meaningful impact on the team, as Alexander-Walker and Satoranský would be traded again the next day to acquire the second-round pick that eventually turned into Jabari Walker, and Louzada appeared in a total of seven games before being cut in the off-season. Not even the first-round pick would end up conveying, as its protections meant it would only head to Portland if it landed between picks 5-14, but it ultimately ended up being the 15th pick in the draft after the Pelicans made the playoffs and sent the pick to Charlotte, where it would eventually become Mark Williams.
The only positive thing to come out of the 2022 season was the development of Anfernee Simons. The 24th overall pick in the 2019 NBA Draft, Simons had been waiting for his opportunity to show his potential, and with Lillard out for the season, he stepped into the point guard role and immediately proved himself. Upon moving into the starting lineup, he took his game to another level, averaging over 23 points with nearly six assists per game on 45.6/42.3/86.6% shooting splits over his next 27 games. Eventually, Simons too would be shut down for the season with a lingering knee issue as the Blazers ended the season by going 2-21 after the All-Star break in an attempt to secure better lottery odds.
Despite having the sixth-best odds at the first pick, Portland fell back to the seventh slot where they were able to draft Kentucky wing, Shaedon Sharpe. After initially being ranked as the top player in the 2022 high school class, Sharpe decided to graduate early and enroll at Kentucky in the fall. Despite being enrolled, he never ended up playing for the team, which resulted in him becoming the biggest mystery in the 2022 NBA Draft and ultimately falling to the Blazers at seven.
The big off-season move the Blazers made to try to build around Lillard was trading a future first-round pick for Jerami Grant, a former role player for winning teams who had developed into a pseudo-star with the Pistons. He had turned down a chance to contend for titles in a supporting role with the Nuggets, rather opting to sign a three-year, $60 million contract to be the best player on a Detroit team that was coming off a 20-win season. He went on to average over 20 points per game across his two seasons with the Pistons, but his team won a total of 43 games during those two years, never even sniffing the playoffs. The talent was obvious with Grant, but there was no evidence to suggest that his teams could succeed with him playing in a starring role.
The season started well for the Blazers, winning 10 of their first 15 games as Lillard averaged over 27 ppg. On November 19, Lillard suffered a calf strain that would sideline both him and Portland’s winning ways for the next two weeks. During his absence, the Blazers won only two of their eight games, falling back to a record barely above .500, at 12-11. Even when he returned, Portland continued their mediocre play. By the All-Star break, their record sat at two games under .500, placing them outside the playoff picture. That stretch was highlighted by Lillard scoring his 18,041st point in a Trail Blazers uniform on December 19, passing Clyde Drexler for the most in franchise history.
After using his free time during the All-Star break to capture the Three-Point Contest title, Dame kept that momentum going into his first game back. On Sunday, February 26, Damian Lillard decided to obliterate the Houston Rockets, dropping 71 points to set a Trail Blazers franchise record. En route to his 71 points, he drained 13 three-pointers, also the most in Blazers history, and shot 22/38 from the field overall. His 80.4% true shooting percentage was the highest of the eight players who had scored over 70 points in a game, which went along with the 89.8% clip he hit earlier that year against the Utah Jazz, the highest of any player in a 60+ point game. Additionally, Lillard became the oldest player to score over 70 points in a game, and the only player to do so while playing under 40 minutes and hitting more than 10 threes.
Despite Lillard’s incredible play, averaging over 35 ppg after the All-Star break, the Blazers were not able to keep pace with the rest of the Western Conference, falling well out of the playoff picture. Sitting with a 32-40 record, the Blazers decided to shut down Dame for the rest of the season, winning only one of their final 10 games as they once again tanked for a chance at better lottery odds.
Portland went into the off-season at a crossroads. Did they want to continue to build with their young core of Simons and Sharpe, or did they want to take one last swing at contending with their superstar? When they landed the third pick in the 2023 draft lottery, it only magnified the stakes of that decision. That pick represented the future of the franchise in two ways, as a piece they could move to get Dame help, but also as the potential star to replace him.
After months of rumors surrounding the Blazers' decision, they ultimately decided to keep the pick, drafting Scoot Henderson, another point guard. After no trades, and the only significant free agent move being to re-sign Jerami Grant to a 5-year, $160 million contract, Lillard officially requested a trade on July 1.
Atop the list of teams Lillard wanted to play for was the Miami Heat, but the Blazers weren’t buying what they were selling. Miami’s potential trade packages all centered around Tyler Herro, but with Portland already having Simons, Sharpe, and Henderson on the roster, three young guards who all needed minutes to grow, they didn’t want to take on yet another one in Herro.
As Lillard had just signed an extension the previous off-season, keeping him under contract through the 2027 season, Portland had no reason to take immediate action, as a better offer would eventually come. With neither team willing to budge on the trade package they wanted, Lillard was left hanging in limbo, and the Blazers were left waiting for a better package to come along.
After a three-month standoff full of rumors and theories, that offer eventually did come along, and Dame was sent to Milwaukee to team up with Giannis Antetokounmpo.
Playing with a two-time MVP who led the Bucks to their first championship since 1971 will give Lillard the best chance he’s ever had to truly contend for a title. Milwaukee’s coming off a 58-win season that saw them finish as the top team in the Eastern Conference before being upset in the first round of the playoffs by the Heat. During that series, a back injury forced Antetokounmpo to miss two games and limited him in the others, exposing the Bucks’ lack of shot creation without him. In addition to swapping out Holiday for Lillard at point guard, they also replaced Head Coach, Mike Budenholzer, with former Toronto Raptors assistant, Adrian Griffin.
The Lillard trade immediately turned the Bucks into favorites to win this season's NBA title. The combination of Dame and Giannis will be one of the greatest offensive duos in NBA history. Neither of them has ever played with a player as good as the other, and their skill sets should complement each other perfectly. Lillard’s gravity as a three-point threat will open up driving lanes for Giannis, whose drives will draw in the defense to give wide-open threes to shooters like Dame and Kris Middleton. Additionally, the Dame-Giannis pick and roll will be terrifying for opponents and will make them one of the league’s most efficient closing offensive units.
While making the switch from Holiday to Lillard will be a significant upgrade offensively, it will be as much of a loss on the defensive side of the ball. Holiday is a five-time All-Defensive Team selection, and is widely considered to be the best guard defender in the league, so going from him to Lillard, who has been a negative defender throughout his career, will be a big loss for the Bucks. Milwaukee’s hope is that by placing Lillard in front of Antetokounmpo, a five-time All-Defensive Team member and the 2020 Defensive Player of the Year, and Brook Lopez, a two-time selection who finished as the runner-up for last year’s award, will make up for the loss of Holiday by giving Dame the best defensive teammates he’s ever played with.
Portland, meanwhile, will look to build around a new young core as Joe Cronin will finally get a chance at the rebuild he’s been wanting after failing to build a contender around Lillard since taking over as GM in 2021. Simons is still only 24 years old, and Henderson and Sharpe are only 19 and 20, respectively, making them one of the league’s most exciting young cores. Ayton is a former first-overall pick who’s still only 25 and will get a chance at a fresh start in Portland, and Robert Williams is only 26 and a perennial Defensive Player of the Year candidate when he’s healthy. While Grant is 29 and still owed $160 million over the next five years, his trade value has never been higher, and Brogdon is coming off a Sixth Man of the Year Award and should bring significant return from a contender looking to bolster their depth at the trade deadline. Needless to say, the future looks brighter in Rip City than it has in years, and as the Blazers move into the post-Dame era, they have a blueprint for success, it will just come down to following it in the coming years.
poetic