Should Sixers Avoid Lillard Sweepstakes After Latest Message?

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At last, Damian Lillard no longer wants to play for the Portland Trail Blazers. With a decision that probably came two years too late, Lillard has told Portland’s management that he’s finally ready to move on. To no surprise, the Philadelphia 76ers were immediately linked to the star guard.
When the Sixers navigated through the trade market, dangling the three-time All-Star Ben Simmons, the league-wide assumption was that the Sixers were holding out hope for a Lillard trade request so they could swap disgruntled stars.
Behind the scenes, Lillard remained quiet on the trade front. Publicly, he told media members in Philadelphia to spread the message that he was ten toes down in Portland. The dreams of trading for Damian Lillard were gone, and the Sixers moved on to another target.
Months later, the Sixers landed James Harden in a blockbuster trade headlined by Ben Simmons. A season and a half later, the Sixers are facing the same situation. Their primary point guard wants out, and Damian Lillard is right there for the taken.
So, James Harden doesn’t want to play for the 76ers? The logical move would be to put a competitive package together and ship him out to land Lillard some way. However, there is another reality that the Sixers and many other teams have to face; Dame Lillard doesn’t want to play for them either.
Within moments of Lillard’s trade request becoming public news, the Miami Heat were the immediate favorites to land his services. Sure, he’s shown potential interest in joining the Brooklyn Nets recently, and the Sixers have a playoff-ready roster with an MVP in the mix, but Lillard’s desired destination has become Miami or bust.
ESPN NBA Insider Adrian Wojnarowski painted the picture of Lillard’s current thinking on Thursday.
“As Cronin explores the broader landscape, Lillard's agent, Aaron Goodwin, has been calling prospective trade partners and warning against trading for his client, team executives told ESPN. Goodwin is telling organizations outside of Miami that trading for Lillard is trading for an unhappy player. As interference goes, this is a time-honored agent maneuver to depress offers and clear a path to a predetermined destination.”
Considering this isn’t messaging from an anonymous source, teams can’t take this with a grain of salt. Lillard wants to go to South Beach and seems to be extremely stubborn about the situation as a whole.
According to Wojnarowski, unnamed GMs mentioned that pressure from Lillard’s camp “won’t impact” their pursuit and believe if they land Lillard, he would “remain playing hard and well.”
Considering the latest narrative surrounding the suddenly disgruntled NBA All-Star, should the Sixers withdraw from the Lillard sweepstakes?
The Sixers have a small window they have to maximize. On the surface, pairing Damian Lillard, a seven-time All-Star, with Embiid could be a dangerous duo for years to come since both players have multiple seasons attached to their contracts.
But one of the biggest questions, aside from Lillard’s supposed lack of motivation to play for a non-Heat squad, would surround the star guard’s health.
Turning 33 on July 15, Lillard hasn’t played in more than 67 games in a single season since the Blazers’ 2018-2019 run. Last year, he appeared in just 58 games after appearing in 29 games one year prior. Once a consistently healthy player, Lillard has seen his fair share of health struggles lately, similar to Philly’s current veteran guard, James Harden.
Considering a package to trade for Lillard would more than likely start with the Sixers’ young guard Tyrese Maxey, the Sixers would have to think long and hard about the player they would be giving up in a hypothetical deal.
While the Sixers are rumored to be keeping Maxey off the table in all and any trade discussions this offseason, there could be a moment when the Sixers’ front office thinks Lillard might give them their final shot to take advantage of the current window if the Harden situation can’t be salvaged.
But the risk-reward of making that trade-off might not be worth the gamble. Without a championship appearance on his resume, Lillard’s presence doesn’t guarantee the Sixers book a ticket to the 2024 NBA Finals.
As much as Daryl Morey and the Sixers want to go all in, Maxey’s rapid development over his first three NBA seasons could leave the Sixers confident they could win now with Maxey improving more once again while having him become a cornerstone player they build around for years to come.
Somebody out West has to budge in this situation. Typically, NBA superstars get their way and land in their preferred destination, but the Blazers are standing firm on taking the best package available, which doesn’t seem to be coming from Miami.
The Sixers might have the tools to help Portland get their way, but taking on the risk of having a third-straight potentially disgruntled ball-handler with recent injury concerns while giving up valuable assets could lead the Sixers down a dark path. Anything can happen as the situation plays out without a conclusion, but the Sixers should be extremely cautious if they remain in the Lillard sweepstakes.
Justin Grasso was a credentialed writer and publisher covering the Philadelphia 76ers for Sports Illustrated’s Philadelphia 76ers On SI Network. Grasso got his start in sports media in 2016 with FantasyPros, working the news desk, providing game-by-game player analysis and updates on the Portland Trail Blazers and the Golden State Warriors. By 2017, he joined FanSided’s Philadelphia Eagles site as a staff writer. After spending one season covering the Eagles as a staff writer, Grasso was promoted to become the site’s Co-Editor. For the next two NFL seasons, he covered the Eagles closely before broadening his NFL coverage. For a brief stint, Grasso covered the NFL on a national basis after joining Heavy.com as an NFL news desk writer. In 2019, Grasso joined the 76ers' beat on a part-time basis, stepping into a role with South Jersey’s 97.3 ESPN. Ahead of the 2019-2020 NBA season, he concluded a three-year stint covering the Eagles and joined the Sixers beat full-time. Grasso has covered the 76ers exclusively since then for Sports Illustrated. He is a member of the Pro Basketball Writers Association. Twitter: @JGrasso_ Instagram: @JGrassoMedia Threads: @JGrassoMedia
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