Damian Lillard is in his 10th season with the Trail Blazers, placing him in rarefied air as one of the few active former lottery picks to have spent 10 or more years with the franchise that selected them.
Lillard, who came in at third on SN's point guard rankings ahead of the 2021-22 season, has been one of the league's best talents over the last several years. However, the Trail Blazers have bowed out in the opening round of the playoffs in four of the last five seasons.
MORE: Ranking the NBA's best players entering the season
Now 31 years old, many believe that Lillard's loyalty to the franchise could be running thin because of a lack of overall team success during his time in Portland. While Lillard is under contract with the Trail Blazers through at least the 2023-24 season, a lackluster 2021 offseason has led many to believe that he might not be with the franchise for the duration of his deal.
How did things get to this point? The last few months of various reports, moves by the franchise and statements from Lillard can provide an idea.
How did Damian Lillard react to the Trail Blazers' elimination from the playoffs?
Despite Lillard averaging 34.3 points, 10.2 assists and 4.3 rebounds, the Trail Blazers were eliminated in six games by the Nuggets in the opening round of the 2021 NBA playoffs.
Following the loss, Lillard spoke on the Trail Blazers' roster configuration, saying that, "I don't know what a shakeup looks like or what changes will be made or could be made, but obviously as it is, it wasn't good enough. ... Where we are isn't good enough to win a championship if it's not good enough to get out of a first-round series with two of their best three or four players not on the floor."
Damian Lillard on if the Blazers need changes this offseason: "Obviously where we are isn't good enough to win a championship if it's not good enough to get out of a first round series with two of their best three or four players not on the floor." pic.twitter.com/gbXkqDko0s
— Royce Young (@royceyoung) June 4, 2021
On June 4, Lillard shared a post on Instagram with the caption, "How long should I stay dedicated? How long til opportunity meet preparation?" While many interpreted it as cryptic, taking the caption at face value would be acknowledging it is a lyric from Nipsey Hussle's "Dedication."
That same day, the Trail Blazers and head coach Terry Stotts, who was hired the same season that Lillard was drafted, mutually agreed to part ways. Chauncey Billups was hired as Stotts' replacement on June 27.
MORE: Where does Billups rank among new head coaches?
How did Damian Lillard respond to trade rumors?
On the morning of July 16, Henry Abbott of TrueHoop reported that Lillard would soon request a trade, saying, "If this is a surprise, you haven't been paying attention."
Hours later, Lillard addressed the report following Team USA practice, saying that the report was not true.
"I haven't made any firm decisions on what my future will be," Lillard said.
Damian Lillard says he woke up to reports of him on the verge of requesting a trade “is not true.” And says secondly, “I haven’t made any firm decisions on what my future will be.”
— Chris Haynes (@ChrisBHaynes) July 16, 2021
In a one-on-one with Yahoo Sports' Chris Haynes, Lillard expounded upon his position:
"I think that's the stage we're at as a team where we all, not just me, not just my teammates, not just our new coaching staff, the front office, everybody in this organization must look in the mirror because we've constantly come up short. We have to look in the mirror and say I have to be better because whatever it is we're doing is not working and it's not giving us the shot to compete on the level that we want to compete on."
MORE: Lillard one of 11 active players selected to NBA 75 team
What did Damian Lillard say ahead of the 2021-22 NBA season?
After winning gold with Team USA in Tokyo, Lillard returned to the U.S. and took to Instagram to reaffirm his commitment to the franchise, posting a photo on Sept. 8 with the caption, "Back for more… #RipCity is my city."
At the Trail Blazers' media day, Lillard had this to say about the team's status leading into the season:
"Obviously, at the end of last season, I wanted to see our roster improve. I wanted us to have a better chance to win. And we had our conversations throughout the summer about what that looked like, and how we could take steps in that direction. I come into this season with faith that that's going to happen."
In addition to firing Stotts and hiring Billups, Portland's offseason included the acquisitions of Ben McLemore, Larry Nance Jr., Tony Snell and Cody Zeller.
Damian Lillard's contract
In June of 2019, Lillard signed a four-year supermax extension worth $196 million. The deal keeps Lillard with the Trail Blazers through at least the 2023-24 season and has a player option for the 2024-25 season worth $48.8 million.
| Year | Age | Salary |
| 2021-22 | 31 | $39,344,900 |
| 2022-23 | 32 | $42,492,492 |
| 2023-24 | 33 | $45,640,084 |
| 2024-25 | 34 | $48,787,676 |
(All salary figures via Spotrac)
