After spending all 11 years of his professional career with the Portland Trail Blazers, Damian Lillard finally requested a trade last June.
Lillard’s demand no longer came as a shock as Portland’s recent struggles turned the prospect of a trade from an “If” to a “When”.
Since the Trail Blazers made a surprise run to the Western Conference Finals in 2019, they dropped out of the postseason in the first round during the next two seasons before failing to qualify at all for the playoffs over the past two campaigns.
The 33-year-old’s chances of winning an NBA championship are slowly slipping away and it seems like even he, a superstar who has pushed to make his name synonymous with loyalty over the past decade, has his limits when it comes to losing.
What’s peculiar about the circumstances surrounding Lillard’s request though is that three months have already passed since his initial demand. Typically, cases like this are swiftly resolved as teams try to avoid the drama that accompanies these trade requests.
For example, it took the San Antonio Spurs around one month to trade away Kawhi Leonard to the Toronto Raptors after he made it known during the 2018 offseason that he wanted out. Similarly, James Harden has already made two successful trade demands over the past four years as it took the Houston Rockets and the Brooklyn Nets just a few weeks to find a new home for the 2018 NBA Most Valuable Player.
However, one recent situation that parallels that of Lillard is the messy break-up between Anthony Davis and the New Orleans Pelicans. Davis unwisely made it clear that he wanted the Pelicans to trade him only to the Los Angeles Lakers before the 2019 NBA Trade Deadline. This gave the Pelicans leverage over the Lakers which allowed them to drive up their asking price for their franchise cornerstone.
Once the trade deadline elapsed with no deal in place, Davis decided to sit out the rest of New Orleans’ games before the NBA stepped in and threatened the team with fines if he did not suit up. Close to four months after the trade deadline, the Pelicans finally shipped Davis to Los Angeles for a package that looked like a massive overpay at the time.
Lillard’s episode is quite comparable with that of Davis, given that he has made it clear that the Miami Heat are his preferred destination. He actually had a chance to have more flexibility on what team he plays for, yet he decided to sign a maximum extension with Portland last year that has him under contract until 2027.
The biggest hurdle preventing Lillard from joining the Heat is actually the Heat themselves.
Miami’s front office, led by their mythical team president Pat Riley, is notoriously shrewd. This is a disciplined group that is, more often than not, on the winning end of deals. They are also coming off their second NBA Finals appearance over the past four years–the most among any team in the league–which is where the similarities with regards to the Davis conundrum end.
Back in 2019, the Lakers were in desperate need of an NBA All-Star to pair with LeBron James as they failed to make the playoffs in the prior season. This made the king’s ransom that they paid for Davis justifiable and it paid off as they won the 2020 NBA Title.
For the Heat, it would not be out of character if they decided to simply move on to the next target if they feel like the Trail Blazers are asking for too much in return for Lillard.
As a matter of fact, that next target seems to have already come up.
Giannis Antetokounmpo, another player who is known for his loyalty, recently made comments that he is open to moving on from the Milwaukee Bucks if they no longer present him with the best chance to win it all.
The two-time NBA MVP Antetokounmpo is obviously a much bigger prize than Lillard given that he is five years younger, almost one foot taller, and much more athletically gifted. The side-by-side comparison of their resumes is all that one needs to see to settle whatever debate there was on who the better player between the two is.
More importantly, Antetokounmpo has proven that he is a viable cornerstone for a winning team as he led the Milwaukee Bucks to the 2021 NBA championship.
It would make sense if teams such as Miami saved their assets for a potential Antetokounmpo trade which Zach Lowe, one of the top NBA pundits today, recently cited.
What this means for Lillard is that he may have to swallow his pride and either continue suiting up for Portland or accept a trade to another team besides the Heat. Lillard is bound to take a backseat to Antetokounmpo and the Trail Blazers seem destined to accept a lesser package for their longtime franchise icon.
Portland has a bright future ahead of themselves with this year’s third overall pick Scoot Henderson all set to take Lillard’s place as their team’s point guard. Incoming sophomore Shaedon Sharpe, who has drawn comparisons to the legendary Kobe Bryant, is another up-and-coming player to look out for on their roster as well.
It will be interesting to see how this situation plays out in the coming weeks and though Lillard may not ultimately end up with his desired trade to Miami, all is not lost in his quest for an NBA championship. If the Trail Blazers decide to tone down their demands, it would be a major boost for whatever team lands the seven-time NBA All-Star as it lands them his services without sacrificing their depth.
Furthermore, two of the recent trade demand instances cited above–that of Leonard and Davis–led to championships in their first season with their new team. Lillard may not be able to win a championship as the top player on a team, but he is sure to have a title-winning impact if he winds up in a situation where he can be a co-star rather than a solo act like he has been in Portland since LaMarcus Aldridge’s departure in 2015.
All signs point to “Dame Time” finally running out for the Trail Blazers and it seems like it has too for the trade market with the thought of acquiring Antetokounmpo looming large over most teams. While this situation is far from ugly when compared with other trade demands, Lillard’s career may, as unfortunate as it sounds, wind up becoming the latest cautionary tale that loyalty is never rewarded when it comes to the NBA.