From the moment Neil Olshey got fired from the Portland Trail Blazers front office, NBA fans worldwide have been firing up their trade machines.
The general hope is that superstar point guard Damian Lillard may finally be ready to move on from the franchise, and that has fanbases around the league salivating at a potential earth-shattering trade. Especially fans of the Boston Celtics were very excited by a recent ESPN article postulating a possible trade idea that saw the star guard head to the East Coast.
Lillard is one of the best guards in the NBA and has been incredibly loyal to the Blazers over the years, so this isn’t a scenario where he will end up at some random team, but rather, should he move, he will have a say in his next destination.
In the modern NBA, a significant factor that goes into a player’s decision-making process when choosing their next team is who their teammates will be. And according to Bleacher Reports’ Jake Fischer, Lillard has an idea of which players he would like to team up with, should any trade materialize.
“(Ben) Simmons was one of several defensively-minded wing players who Lillard has expressed interest in playing with since the 2020 offseason, along with Jaylen Brown and Aaron Gordon,” Fisher wrote.
Of course, the Philadelphia 76ers have the strongest trade package, but trading Simmons for Lillard wouldn’t make sense considering the superstar wants to play with the want-away guard.
Lillard’s Contract Will Be a Stumbling Block
According to Spotrac, Lillard is set to earn $176 million throughout his current contract, meaning the six-time All-Star is poised to pocket $47.7 million at the age of 34. Most self-respecting NBA teams will approach that type of deal with cautiousness, given that one injury could hamstring their franchise for the next three to four years.
Herein lies the issue for the Celtics. In recent history, the team has been burnt by again guards, with Kemba Walker previously joining the team on a max deal, only to rapidly decline during his second year. Adding Lillard on an even bigger contract while still running similar risks would be a significant roll of the dice.
Furthermore, the Celtics have previously tried pairing Jayson Tatum and Brown with a third scorer, and figuring out the hierarchy has been a significant issue for the roster. Now, with Tatum clearly ascending towards All-NBA talent and Brown only a step or two behind him, it isn’t clear where Lillard would fit into that ecosystem.
Lillard Wants More Money
According to a recent article from ESPN’s Adrian Wojnarowski, Lillard is looking to tack on another two years to his current deal, which would see him under contract until he’s closing in on age 37.
The proposed extension would be two years at $107 million in the region. “The prospects of Portland extending Lillard, 31, beyond his $48.8 million in 2024-25 to pay him $51 million at 35 years old and $55 million at 36 threatens to turn an asset of a contract into an albatross,” Wojnarowski wrote, as he detailed the issues tied to paying Lillard deep into his thirties.
The concern for any teams interested in trading for Lillard is that he may want guarantees of a similar extension in the future, as he aims to become the league’s highest-paid elder statesmen.
Perhaps a team is willing to cough up that kind of money down the line to have a shot at winning a championship within the next two years. It’s certainly possible a front office would feel good about making that deal, but would they regret it when Lillard is a role player earning max player money?
Celtics President of Basketball Operations is a brilliant basketball mind, and it’s unlikely that he pulls the trigger on any deal where a player is holding the front office to ransom on a potential extension. But still, a possible big three of Lillard, Brown, and Tatum has championship written all over it. The only question is, is it worth the cost?