Why a Ben Simmons, CJ McCollum trade makes too much sense for both Trail Blazers and Sixers

The Portland Trail Blazers moved on from basketball executive Neil Olshey and the future of Damian Lillard and CJ McCollum is in question.

Lillard, a six-time All-Star who has been one of the best scorers in the league for the past several seasons, becomes eligible to sign a supermax extension ($106.6 million over two years) on July 6.

Before he commits to remaining under contract with the Blazers until the 2026-27 season, however, there are some obvious concerns that he needs the team to address. First and foremost, he has concerns with the roster that he reportedly believes could be solved with a trade (via The Athletic):

“Multiple sources have told The Athletic that Lillard would like to play with Philadelphia 76ers three-time All-Star Ben Simmons. The Trail Blazers’ league-worst defense would instantly improve, and sharing a backcourt with a non-shooter could work given Lillard’s high-volume usage.”

It makes sense that Lillard would want to play alongside Simmons, whose defensive impact and versatility would help solve some of the limitations that Portland’s defense has had over the past several years.

But in order to do that, according to the most recent reports, Portland would have to include McCollum as a centerpiece:

“Sources say the Trail Blazers, under Olshey, discussed the framework of a trade for Simmons, moving CJ McCollum, a first-round draft pick and a young player such as Nassir Little or Anfernee Simons to Philadelphia. The 76ers, sources said, at one point asked the Trail Blazers for McCollum and multiple draft picks and multiple draft swaps, which Portland rejected.”

Olshey, who ran the front office for the Trail Blazers for the past decade, had especially strong loyalty towards McCollum.

The former executive was very influential in the scouting and decision-making process that brought the former Lehigh guard to Portland and he was reluctant to move on from someone who he had considered his home-run draft pick.

So with Olshey out of the picture, it is more likely than ever before that the team moves on from McCollum.

The pairing of McCollum and Lillard has had definitive problems on the defensive side of the floor and those issues were strong enough to worsen the potential of success the organization could have in the postseason. Simmons, a star who is disgruntled in Philadelphia, doesn’t have those same concerns.

McCollum, meanwhile, would instantly help solve some of the floor-spacing issues that the Sixers have faced with Simmons in the mix. He is an excellent option on the perimeter to flank alongside Joel Embiid, who dominates in the post.

The swap just makes too much sense — it has been obvious for years — but the longer that it takes to happen, it seems the less likely such a deal will ever actually occur.