Damian Lillard has always been loyal to the Portland Trail Blazers franchise. Lillard has been the key to their ability to make the playoffs every season, but the furthest that the Trail Blazers have gotten is the Western Conference Finals. Damian Lillard is yet to play in the Finals, and the Portland Trail Blazers' roster doesn't look like it is capable of getting there, even with Lillard's monster offensive explosions.
Perhaps a trade would allow Damian Lillard to be on a team where he has the potential of making the Finals and competing on the biggest stage. The 76ers are a team that could be interested in Damian Lillard: he would provide them with another superstar to pair with Joel Embiid. Here is a trade package that would be interesting for both teams.
Philadelphia 76ers Receive: Damian Lillard
Portland Trail Blazers Receive: Ben Simmons, Tyrese Maxey, Shake Milton, two future first-round picks
Joel Embiid has looked unstoppable so far in the playoffs. There seems to be no center who can stop him on the interior, and he is also shooting 42.9% from beyond the arc in the playoffs. He is a force to be reckoned with, and he has had an MVP caliber regular season this year, averaging 28.5 PPG and 10.6 RPG as the leading superstar of the 76ers. The 76ers are a great team already, but if they fall below expectations in the playoffs, there could be some changes to the team.
If Damian Lillard were traded for the 76ers, he and Joel Embiid could create an unstoppable duo that would be reminiscent of a Kobe Bryant and Shaquille O'Neal pairing. Damian Lillard is still at his peak, and Joel Embiid is just entering his prime. Both draw a lot of attention to themselves from defenders as the primary scorer on the team, so pairing the two on the same team would be absolutely deadly for opposing defenses.
In this trade scenario, Tobias Harris would still be on the team and would be a perfect third option for Lillard and Embiid. Matisse Thybulle is a proven defensive stopper, and he simply has instincts for that end of the floor. The 76ers would still have a solid core around their superstars, and Lillard and Embiid would clearly be a duo that has the offensive firepower to win it all.
The Damian Lillard era in Portland has been great, with the team enjoying a solid winning stretch. But if Damian Lillard were traded, it would signal the start of a rebuild. This package would give them some young prospects that could headline the rebuilding process.
Ben Simmons is here for obvious reasons: it is likely that the Trail Blazers would want a young centerpiece which they can build around, and Ben Simmons fits that category. Simmons is a defensive artist, able to guard 1-4 very effectively, with some ability to guard the bigger 5s of the league. On the offensive end, he's a talented finisher and facilitator. Ben Simmons is a great two-way player with elite athleticism, and he could improve even further in a more featured role.
Tyrese Maxey and Shake Milton are both capable young guards, who could develop well in bigger roles. If Damian Lillard is traded, then it is likely that his co-star CJ McCollum will be traded as well, so there will be plenty of minutes to go around in the backcourt. Tyrese Maxey in particular has shown some scoring potential, and it'd be interesting to see him develop in an environment where he'd get more usage. The two picks from Philadelphia would also help the Trail Blazers' future. Overall, this is a package that gives the Portland Trail Blazers what teams generally want in a rebuild: talented young players and picks.