NBA Offseason Weekly: Lillard Locked-In to South Beach?
The major players in NBA free agency were scooped up rather quickly on June 30. Most of the best players who were available re-signed with their teams, including Kyrie Irving, Khris Middleton, Draymond Green, Jerami Grant, Brook Lopez and Cam Johnson. The Los Angeles Lakers re-signed forward Rui Hachimura and guards Austin Reaves and D’Angelo Russell.
The offseason has not been without drama, though. We saw a couple of minor trades, including guard Max Strus to the Cleveland Cavaliers and forward Grant Williams to the Dallas Mavericks. The big fish are still available – guards James Harden and Damian Lillard. Both players could cause a power shift in the association, making a big impact on NBA betting.

Last week in NBA offseason weekly, we looked at where Harden could be traded. Lillard officially requested a trade last weekend. Let’s look at Lillard’s timeline and his potential landing spots. Lillard’s destination will likely have a bigger impact on sports bets than Harden’s relocation.
Timeline to Trade Request
Trade rumors have swirled around Lillard for a couple of years. Since the Blazers’ last postseason appearance in 2021, many have suggested Lillard could want out. He is one of the best guards of this generation but has yet to win an NBA championship. At 32, Lillard is still scoring at a high clip. In fact, he comes off a career average of 32.2 points and joined the 70-point club with 71 points on Feb. 26. If Lillard wanted out of Portland, teams would come calling.
Last year, the seven-time All-Star was in consistent trade rumors. Lillard remained loyal to the Trail Blazers, who drafted the 6-foot-2 guard out of Weber State in the 2012 NBA Draft.
“I have no plans of not being a Portland Trail Blazer,” Lillard said. “I want to be here, and I think they want me here.”
Lillard’s dedication to Portland has felt similar to LeBron James’ goal of winning the Cleveland Cavaliers a championship. Who knows, maybe Dame will follow the LeBron route, rejoining the Blazers after winning a title elsewhere. So what was the final straw for Lillard?
Portland has been in a weird spot over the last couple of years. The franchise has not been close to making the playoffs, or even the Play-In Tournament, finishing the previous two seasons well under .500. Portland seemed to go against Lillard’s wishes in the offseason as well.
Brian Windhorst of ESPN reported prior to the draft that Lillard did not want a “youth movement.”
.@WindhorstESPN says Damian Lillard could ask out of Portland if they don’t trade No. 3 pick:
“Dame does not want a youth movement [and] wants to play with veterans.” pic.twitter.com/41iQzvip1g
— Get Up (@GetUpESPN) June 20, 2023
Sam Amick of The Athletic reported Lillard’s “dream offseason” included the Blazers re-signing Grant and acquiring veteran forward Draymond Green in free agency. Portland checked one box after inking Grant to a five-year, $160 million deal, but Green re-signed with the Golden State Warriors.
In the 2023 NBA Draft, the Trail Blazers elected to not trade the No. 3 pick and selected guard Scoot Henderson. Portland spent its last two lottery picks on Henderson and guard Shaedon Sharpe in the 2022 NBA Draft. Plus, the Blazers signed guard Anfernee Simmons to a four-year extension in the 2022 offseason.
Simmons averaged 21.1 points last season, Sharpe averaged 23.7 points in the final 10 games of the 2022-23 season, and Henderson is the sportsbook’s second-favorite to win Rookie of the Year (+325). Portland has formed one of the most promising young backcourts in the NBA, signaling the franchise could be ready to move on from Lillard.
Apparently, this was enough for the veteran guard. On Saturday, July 1, Lillard officially requested a trade.
Sources: Trail Blazers star Damian Lillard requests trade – via @ESPN App https://t.co/tdFdlIbLia
— Adrian Wojnarowski (@wojespn) July 1, 2023
Lillard Makes Intentions Clear as Day
About one week later and Lillard’s future is still unclear. Which franchise will acquire the elite scoring guard? What is the latest on Lillard?
The Miami Heat have been the overwhelming favorite for the entire process. NBA odds are not even offering lines for the Heat. Instead, online gambling is offering odds for Lillard’s next team if not the Blazers or Heat. The Brooklyn Nets have the shortest odds for this bet (+125), with the New York Knicks as the second-favorite (+350).
We are likely waiting on trade negotiations. It seems this could be a three-team trade with an outside squad landing Miami’s guard Tyler Herro, who is consistently landing in trade rumors. However, this wait has led to speculation. Some have wondered if this will be a repeat of the Donovan Mitchell sweepstakes of last year.
Mitchell was linked to New York for months, which is his hometown. NBA lines had the Knicks as the favorite for some time. The Utah Jazz and Knicks failed to get a trade done. The Cleveland Cavaliers swooped in out of nowhere, acquiring one of the best guards in the NBA.
Could a surprise team snatch Lillard, offering a trade package too good for the Blazers to pass on? This is unlikely, as multiple reports have claimed Lillard has made it known he wants to play for the Heat.
Mark Medina of Sportsnaut speculated on Thursday what could happen if Lillard is traded elsewhere. Medina wrote, “He just wouldn’t go,” a person familiar with Lillard’s thinking told Sportsnaut. “He just wouldn’t report.”
ESPN’s Woj also said Portland will consider teams that are not on Lillard’s desired list. However, other reports say Lillard’s agent, Aaron Goodwin, is warning franchises the veteran guard will only be happy in Miami.
It sounds like Lillard is doing everything possible to land in South Beach. For now, the Heat still seems like a lock. Few franchises would be willing to unload assets for an unhappy player that could threaten to sit out.