Over the last few weeks, Damian Lillard’s name has been floated around the rumor mill amid reports that he may once again be headed out of Portland. There have been links to the Heat, Knicks, Nets, and even the Pelicans for Lillard’s services despite his stance on being loyal to the Trail Blazers for the entirety of his career up to this point. Over the last 11 seasons, we have watched as Lillard has become one of the greatest three-point shooters in NBA history and one of the 75 greatest players to ever play the game.

Today, just as we have done with other stars such as Stephen Curry and Kevin Durant, we thought we would take a look at the entirety of Damian Lillard’s career season by season while also looking at the amount of money he earned for that season. We will also take a look at his future contracts in order to dive into how they could affect any team that trades for Lillard as well as his career earnings. By doing this, it allows us to determine, based on the market at the time, if Lillard has been undervalued or overvalued at any given point in his career.

This is Damian Lillard’s contract breakdown over the past 11 years and into the future.

2012-13 NBA Season – $3,065,040 Salary

Stats: 19.0 PPG, 3.1 RPG, 6.5 APG, 0.9 SPG, 0.2 BPG

Damian Lillard’s first season in the NBA would be one that set him on his all-time great trajectory. Lillard would immediately start all 82 games for Portland and averaged 19.0 PPG and 6.5 APG on 42.9% shooting overall and 36.8% from three. Lillard was second on the team in scoring to only LaMarcus Aldridge while also leading the Trail Blazers in assists.

Lillard was awarded the NBA’s Rookie of the Year award by beating out number-one overall pick Anthony Davis by over 300 voting points and leading all rookies with his 19.0 PPG. Unfortunately for Portland, the duo of Lillard and Aldridge was not at peak form just yet, and the Trail Blazers would win just 33 games while losing 49. The playoff drought would not last long as Lillard and Aldridge led Portland into the future and became one of the NBA’s most potent pairs.

2013-14 Season – $3,202,920 Salary

Stats: 20.7 PPG, 3.5 RPG, 5.6 APG, 0.8 SPG, 0.3 BPG

Damian Lillard would follow up his stellar rookie season with an even more impressive sophomore season in 2013-14. Lillard would increase his scoring average to over 20.0 PPG while increasing his three-point volume and efficiency to 39.4% shooting on 6.8 attempts from three. Lillard would earn the first All-Star nod of his career as well as an All-NBA Third Team selection to cap it off. This time, Portland would win 54 games and head toward the NBA playoffs for the first time in the Lillard era.

In the first round, Portland drew a tough matchup with James Harden, Dwight Howard, and the Houston Rockets. The Trail Blazers would end the series in six games behind the duo of LaMarcus Aldridge and Lillard. Aldridge averaged over 29.0 PPG, while Lillard added 25.5 PPG, 6.3 RPG, and 6.7 APG. The next round was even tougher for Portland as they faced off with defending Western Conference champions, the San Antonio Spurs. Portland would manage to get just one win in the series and San Antonio would go on to win the NBA championship. Lillard would average just 19.8 PPG on 41.1% shooting overall and an abysmal 17.4% shooting from three in those five games.

2014-15 Season – $3,340,920 Salary

Stats: 21.0 PPG, 4.6 RPG, 6.2 APG, 1.2 SPG, 0.3 BPG

The 2014-15 season would be yet another successful one for Damian Lillard and the Portland Trail Blazers. Lillard’s scoring and playmaking improved, but he was still just one season away from the All-World talent we know him as today. LaMarcus Aldridge was still the number-one option for Portland, but Lillard was the perfect complement to his game. For the second season in a row, Lillard was named an All-Star but missed out on All-NBA honors after making it the previous season.

The good news was that Lillard and Portland were heading back to the NBA playoffs after winning 51 games during the regular season. In the first round of the playoffs, the Trail Blazers drew a really tough and gritty opponent in the Memphis Grizzlies. After falling down in the series 3-0, Portland would manage to get themselves one win before being gentleman swept in five games. Lillard averaged 21.6 PPG but once again completely fell flat from three, shooting 5-31 in the series from beyond the arc or 16.1%.

2015-16 Season – $4,236,286 Salary

Stats: 25.1 PPG, 4.0 RPG, 6.8 APG, 0.9 SPG, 0.4 BPG

The 2015-16 season would be one that looked different than the last few seasons. LaMarcus Aldridge was off to the Spurs while a new era began in their own city. This was the first season that we would get a good look at the Damian Lillard/CJ McCollum duo that would lead Portland into the future. Lillard would have his first season with over 25.0 PPG and earn All-NBA Second Team honors but would miss out on an All-Star Team selection for the first time since his rookie season.

Portland would win 44 games with their new look and qualify as the fifth seed for the Western Conference playoffs. In the first round, fans would be treated to an outstanding matchup between Lillard and Chris Paul at point guard for the Los Angeles Clippers. Portland would win the series in six games behind Lillard’s 22.0 PPG on 34.7% shooting from three. It was the first time in Lillard’s career that he shot over 20.0% from three in a playoff series. Unfortunately for Portland, they would run into one of the greatest teams in NBA history in the second round, the 73-9 Golden State Warriors, who defeated them in five games.

2016-17 Season – $24,328,425 Salary

Stats: 27.0 PPG, 4.9 RPG, 5.9 APG, 0.9 SPG, 0.3 BPG

As a team, the Portland Trail Blazers would take a step back, finishing at the .500 mark with a 41-41 overall record. Once again, Lillard would have a tremendous individual season with 27.0 PPG on 44.4% shooting overall and 37.0% shooting from three on over 7.0 attempts. Lillard would miss out on both an All-Star and All-NBA Team selection despite his great numbers, which can most likely be attributed to the team’s poor overall play.

The Trail Blazers would still be able to qualify for the playoffs as the eighth seed in the Western Conference playoffs. With the elation of making the playoffs quickly came the disappointment of having to go up against the greatest superteam of the decade, the Golden State Warriors. After adding Kevin Durant and already having Stephen Curry and Klay Thompson, the Warriors were far too much for Portland, and they swept them in four games. Lillard was able to muster 27.8 PPG but once again fell apart from beyond the arc with a 9-32 effort from three or 28.1%.

2017-18 Season – $26,153,057 Salary

Stats: 26.9 PPG, 4.5 RPG, 6.6 APG, 1.1 SPG, 0.4 BPG

Something would click for the Portland Trail Blazers and Damian Lillard during the 2017-18 season and they would be back to their winning ways once again. Damian Lillard was back in the All-Star Game, averaging nearly 27.0 PPG while shooting 43.9% shooting from the field. Lillard would also be named to the All-NBA First Team for the first time in his career while leading Portland to 49 wins and a third-place finish in the Western Conference.

For Lillard and the Trail Blazers, their season would end in the first round in upset fashion. Two things went awry for them during the series against the Pelicans that led to their early demise. First, they had no answer for Anthony Davis, who averaged over 33.0 PPG and 11.0 RPG in the series. The second thing that went wrong was Lillard. During the four-game sweep, Lillard averaged just 18.5 PPG and shot 9-32 from three, once again falling short in the NBA playoffs for his team.

2018-19 Season – $27,977,689 Salary

Stats: 25.8 PPG, 4.6 RPG, 6.9 APG, 1.1 SPG, 0.4 BPG

The 2018-19 season would be a season of revenge and vindication for Damian Lillard and the Portland Trail Blazers. Lillard would be an All-Star once again and add another All-NBA Team selection to his credentials, this time with the Second Team. For the fourth straight season, Lillard went for over 25.0 PPG, and Portland would win over 50 games with a 53-29 record, good for another third seed in the NBA playoffs.

In the first round of the playoffs, Lillard and Portland would defeat the Oklahoma City Thunder in overwhelming fashion. The series ended with one of the most iconic buzzer-beaters in NBA playoff history as Lillard rose up from over 40 feet to put the dagger in the series and waved goodbye. He averaged 33.0 PPG on 48.1% shooting from three in those five games. In round two, Lillard and McCollum would combine for 51.5 PPG in the series against the Nuggets, which ended with a Portland win in seven games. In the Western Conference Finals, Portland would meet a familiar end when they were swept by the Golden State Warriors for the third time in the decade.

2019-20 Season – $29,802,321 Salary

Stats: 30.0 PPG, 4.3 RPG, 8.0 APG, 1.1 SPG, 0.3 BPG

The 2019-20 season would be an odd one for the entire world as it came to an end abruptly due to the COVID-19 pandemic. Lillard was an All-Star once more, an annual occurrence at this point, as the team added help in the form of Carmelo Anthony and Hassan Whiteside. The Trail Blazers would struggle before the shutdown, going 35-39 heading into uncertainty. When the season restarted in Disney World, Lillard was prepared to do whatever it took to get his team to the playoffs.

Lillard would not only accomplish that mission, but he would also be named the Bubble’s Most Valuable Player and earn All-Seeding Games honors. It would be the first year that he averaged 30.0 PPG in his career and set a career-high in assists with 8.0 APG. As great as Lillard was, it would not be enough to slow down the Lakers once the season started. The Lakers would eliminate Portland in five games and go on to win the NBA championship later that summer.

2020-21 Season – $31,626,953 Salary

Stats: 28.8 PPG, 4.2 RPG, 7.5 APG, 0.9 SPG, 0.3 BPG

The 2020-21 season is the last time that we saw a Portland Trail Blazers team in playoff or play-in contention. Now in a 72-game schedule, Portland would finish 42-30 on the season, which was good enough for a sixth seed in the NBA playoffs. Lillard was amongst the league’s best scorers averaging 28.8 PPG on 39.1% shooting from three and 45.1% shooting overall.

In the NBA playoffs, Lillard would become a man-possessed and have an incredible first-round series against the Denver Nuggets. In a pivotal Game 5 with the series tied 2-2, Lillard would have an all-time great game with 55 points, one of the highest-scoring games in NBA playoff history, but they lost to Denver 147,140 in overtime. The Nuggets would finish off the series in six games despite over 34.0 PPG and over 10.0 APG from Lillard.

2021-22 Season – $39,344,900

Stats: 24.0 PPG, 4.1 RPG, 7.3 APG, 0.6 SPG, 0.4 BPG

Damian Lillard entered the 2021-22 season as the 10th-highest-paid player in the NBA at the time. Earning just shy of $40 million, Lillard was vindicated by his selection to the NBA’s 75th Anniversary Team during the All-Star celebration that season. Lillard and Portland were suffering away from that spotlight, though, as Lillard was shut down after just 29 games due to an abdomen injury.

In those 29 games, Lillard was not himself as he tried to push through the pain of the injury he had sustained over the summer in The Olympics. Lillard was not healthy enough to keep trying to push through the pain, and Portland made the decision to protect their franchise star. The team would also trade CJ McCollum to the Pelicans at the trade deadline that season as Anfernee Simons began to emerge as a potential star for them as well. Portland would win just 27 games and miss the playoffs entirely.

2022-23 Season – $42,492,492

Stats: 32.2 PPG, 4.8 RPG, 7.3 APG, 0.9 SPG, 0.3 BPG

In the 2022 offseason, Damian Lillard would exercise his 2024-25 player option by signing a two-year, $120 million extension with Portland. Now that he was truly set off the court, he was ready to get back to work on the court. Lillard would have one of the best seasons of his career as an individual in 2022-23, averaging a career-high 32.2 PPG shooting 37.1% from three on over 11.0 attempts.

The season included some memorable performances, including a 71-point game that was tied with the Cavaliers’ Donovan Mitchell for a season-high. Lillard’s tremendous season was overshadowed by poor play on a team level, as Portland would win just 33 games and finish with one of the worst records in the NBA. They were awarded the third overall pick in the 2023 NBA Draft, a pick they will use to try and convince Lillard to stay this summer by possibly using it in a trade for another star.

Future Contracts

2023-24 Season – $45,640,084

2024-25 Season – $48,787,676

2025-26 Season – $58,545,211

2026-27 Season (Player Option) – $63,228,828

After opting into his 2024-25 player option by signing the massive extension in 2022, Damian Lillard is now under contract with Portland for the next three seasons, plus a player option for 2026-27 that is worth over $60 million on the year. By 2025-26, Lillard will be one of the two highest-paid players in the NBA, along with Stephen Curry and just ahead of Kevin Durant. The next three seasons will earn him $152,972,971, and if he opts into his 2026-27 option, that will turn into $216,201,799.

Career Earnings – $451,772,803

As it stands right now, Damian Lillard is already one of the highest-paid players in NBA history. As of September 2022, he was fourth in NBA history trailing only LeBron James, Stephen Curry, and Kevin Durant. He has earned more than such stars as Bradley Beal, James Harden, and Nikola Jokic, who are on pace for historically large contracts during their careers as well. Overall, Lillard has been well worth every penny during his NBA career, although at times he could be considered overpaid, especially when his shooting failed him all of those years in the playoffs.

As the market continues to increase and Lillard tries to find a new home, there has to be a team willing to take on a $50 million and $60 million cap hit that Lillard will be in just two years’ time. For the caliber of talent they are getting, the market may shape up to where that is actually a good price for Lillard, considering how astronomical contracts are getting these days. Whatever the case, Lillard has made just shy of a half-billion dollars in his NBA career. Even without a championship ring, there is no way that can be considered a failure.