The Portland Trail Blazers are staring down the most important offseason of the Damian Lillard Era.
They've done well in recent years, adding talents like Shaedon Sharpe and Jerami Grant to their roster while hiring a head coach with a fresh outlook in Chauncey Billups that could lead them to a higher plane. Front office hires, like that of assistant general manager Mike Schmitz, have dramatically improved their talent evaluation and ability to build a roster that can dominate.
Yet, for all of their effort, they still find themselves a step behind other playoff contenders.
On the one hand, the roster had so many kinks to work out that it was always going to take a couple of seasons to right the ship. All things considered, the Blazers are on schedule in their re-tool (or rebuild).
On the other hand, Lillard's patience continues to wane. The clock is ticking for Portland during their pursuit of star talent.
Thats why these three trades are the ones that the Blazers must make in order to help Lillard in the 2023 offseason.
3 trades Blazers must make to help Damian Lillard in 2023 NBA offseason
Note: Tankathon Draft Lottery Simulator used to determine 2023 NBA Draft order
LeBron James: The King Of The Court Offers His Help
Lakers receive: Anfernee Simons, Nassir Little, Kevin Knox II, Trendon Watford, the 5th overall pick in the 2023 NBA Draft, a 2024 first-round pick and the right to swap first-round picks in 2025
Blazers receive: LeBron James and a 2025 second-round pick
In this trade, the Los Angeles Lakers have decided that it's time to end the LeBron James Era in L.A.
Many believe that such a scenario would require the Lakers to lose in the 2023 NBA Playoffs, likely after suffering an embarrassing defeat. However, this could be the case if L.A. wins a second championship during his tenure with the Lakers as well.
In fact, after playing 4 seasons with the Miami Heat, and then four seasons with the Cleveland Cavaliers in his second stint, LeBron may be a bit overdue for his departure from L.A. with it being his fifth season with the Lakers.
That said, LeBron signed a two-year extension with the Lakers in 2022. Perhaps he would have simply left in free agency had he not ended the 2021-22 season with a sour taste in his mouth from missing the playoffs for the first time in 15 years.
The Lakers, who are aware that they need to play for the future, accept a potential trade demand by LeBron.
Ultimately, they accept a trade package from the Blazers that's headlined by Simons and the fifth overall pick in the 2023 NBA Draft. These will be the first two core pieces of their rebuild (outside of Anthony Davis, who they may trade in this scenario as well).
Meanwhile, the Blazers acquire a player that's still highly productive at 38-years-old, averaging 28.9 points, 8.3 rebounds, and 6.8 assists per game on 50.0 percent shooting from the field in 2022-23.
LeBron is more-than-capable of elevating a new-look Portland squad to championship contention, especially if Lillard, Sharpe, and Grant can mirror their performances from the 2022-23 regular season as well.
The Blazers need to re-sign a handful of their own free agents this offseason: Grant, Matisse Thybulle, Cam Reddish, Jeenathan Williams, and Drew Eubanks, namely.
Nonetheless, their probable starting lineup would be Dame, Sharpe, LeBron, Grant, and Nurkic; a formidable group.
For those that watched the Detroit Pistons teams that Blazers head coach Chauncey Billups starred on, he should have no issue getting them to work together like a hand in a glove.
DeMar DeRozan: The Midrange Master Makes His Mark
Bulls receive: Anfernee Simons, Kevin Knox II, and the 23rd overall pick in the 2023 NBA Draft
Blazers receive: DeMar DeRozan
Another veteran that seems to defy Father Time is Chicago Bulls forward DeMar DeRozan, a player only a year older than Lillard at 33 but whose game is a relic of the days when the midrange reigned supreme.
For the Blazers, who will start multiple players capable of stretching the floor, DeRozan's ability to do damage inside the arc will be highly useful.
As will his playmaking, as the six-time All-Star has developed his court vision and passing ability over the years. Whether he's the primary, secondary, or tertiary facilitator in a lineup, Portland will undoubtedly benefit from his ball-movement and basketball IQ.
DeRozan, averaging 24.5 points and 5.1 assists per game on 50.4 percent shooting in the 2022-23 season, is the type of talent that can take Portland from a team that wins 30-something games to a team winning 40-something games.
However, the Blazers have to decide how he fits into their defense. Acquiring DeRozan could mean that Portland uses Sharpe as a Sixth Man until he becomes a more reliable defender. In that event, they could feasibly start Thybulle or Williams as a 3-and-D wing between Dame and DeRozan.
Yet, as they retain the fifth overall pick in the 2023 NBA Draft, they could also use it on a 3-and-D prospect like UConn Huskies standout guard Jordan Hawkins.
Jaylen Brown: The Heir To The Throne
Celtics receive: Anfernee Simons, Nassir Little, the 5th overall pick in the 2023 NBA Draft, and two future second-round picks
Blazers receive: Jaylen Brown and Payton Pritchard
Where the additions of LeBron and DeRozan were all about the present moment, going after Boston Celtics wing Jaylen Brown is a move that the Blazers make with both the current and future in mind.
Though rookie wing Shaedon Sharpe has all the makings of a star player with his elite shooting and leaping ability, Brown is already an established star player with two All-Star selections in the last three seasons. Frankly, if he wasn't overshadowed by tantalizing All-NBA forward Jayson Tatum, he would likely have even more notoriety.
To that point, while Tatum is the more complete player between he and Brown, Brown is arguably the better scorer. Though streakier from distance than Tatum, Brown has a more advanced ball-handling package, a faster first step, and exceptional finishing ability, talents that enhance his overall scoring potential while he continues to develop his jumper.
Brown, though expending more energy on the offensive end as of late, is also a gifted defender at 6-foot-6 and 236 pounds.
For Portland, his aggressive scoring instincts, ability to score from all three levels, and defensive potential fit in neatly with their perimeter talent. Furthermore, it doesn't matter whether he plays in the backcourt or frontcourt giving Billups greater flexibility in his lineups.
Nonetheless, just as important as the talent he possesses and how he raises their ceiling as a playoff-contender is his age.
Just 26-years-old, Brown is in the prime of his career. He could play out his prime in Portland, both with and without Dame.
With that in mind, Brown could be the best trade target for the Blazers this offseason, though the star wing will certainly have his share of suitors should he become available.