Philadelphia 76ers: Do Damian Lillard and Ben Simmons even fit together?

After a steady stream of leaks through the first month of the 2021-22 NBA season, things became oddly quiet on the Ben Simmons–Philadelphia 76ers trade front; too quiet, if you ask me.

Call it a temporary truce brought on by a quarter of the team having Covid or a wait-and-see Clutch Sports cease-fire as the losses started to pile up, but for a time, it looked like the Sixers would be able to quietly focus on normal basketball things like tweaking on-court fit, instead of constant national stories about a player who isn’t even playing.

It was nice, peaceful, and ultimately fleeting, as the latest Shams Bomb just dropped and foiled any fleeting imaginary armistice Philly fans found.

*sigh* Mondays; am I right?

Alright, so let’s hear it; what is the Simmons camp up to now?

Well, get this; it’s actually not directly from Simmons, at least not directly anyway. No, this latest reporting is about Damian Lillard, a player who so routinely breaks the hearts of fans in the City of Brotherly Love, he may as well already be employed by one of its athletic clubs.

According to a source close to the subject, Lillard is unsatisfied with the Portland Trail Blazers’ current roster and would like to see his team trade for an All-Star-caliber defender, namely Simmons.

… um, okay then.

So, completely ignoring the fact that Joel Embiid is also an All-NBA defender, and he’s arguably a better on-court fit with the six-time All-Star – read about that particular point pretty much anywhere on the internet right now – the biggest issue standing between the desires of Lillard and Daryl Morey has to be the compensation interim GM Joe Cronin is willing to surrender to keep the face of his franchise happy.

A few months back, the Trail Blazers offered CJ McCollum, a first-round pick, and a young player like Anfernee Simons and/or Nassir Little to get a deal done. Morey countered with McCollum and many more first-rounders, a deal that Cronin’s predecessor, Neil Olshey opted to shoot down because he reportedly really liked the roster he put together. But as desperation sinks in, could the Trail Blazers come back to the table with an offer Philly can’t refuse? Could the Sixers secure a viable secondary scorer to sandwich between Tyrese Maxey and Danny Green, a developmental player like Little who may become a starter before his rookie-scale contract expires, and enough draft picks to trade for a star player should some squad want to blow things up?

I guess that depends on how well the Portland Trail Blazers feel Ben Simmons and Damian Lillard would fit together, Philadelphia 76ers fans.

Ben Simmons may miss the Philadelphia 76ers if paired up with Dame Time.

For the sake of argument, let’s assume a hypothetical trade between the Portland Trail Blazers and Philadelphia 76ers would see the former send CJ McCollum, Nasir Little, and picks to the City of Brotherly Love for Ben Simmons. Yes, the deal could expand out, players like Robert Covington and Larry Nance Jr., or even Norman Powell could get in on the action, but to make things easy, let’s say that’s the deal. In that ecosystem, where does Simmons fit?

Well, he probably doesn’t start at point guard, not in a backcourt that also features 6-foot-2 NBA 75th Anniversary team member Damian Lillard on the team. A crushing blow to Simmons’ ego? Maybe so, but of the teams potentially interested in a Simmons trade, only a few would humor his desire to be announced as a point guard at the start of games.

How about at shooting guard? Sure, I guess that’s possible, but again, with Powell and Anfernee Simons already in place, it’s hard to see that making a whole lot of sense outside of a semantic desire to remain in the backcourt.

Okay, okay, that’s cool; NBA positions basically don’t matter anymore, as even All-Star teams are no longer rigidly position-specific. You say small forward, I say offensive set pacesetter, we can both be right.

So, assuming Simmons gets a start either small or power forward next to either Covington or Nance, would his responsibilities change significantly from Philadelphia?

In a word? Sorta.

On defense, they’d likely stay relatively similar. Even if Simmons is listed at power forward, he’d likely serve as Chauncy Billups’ point of attack defender, and an ability to get on an island with opposing guards like Steph Curry or James Harden. But on offense? Simmons would have to change things up pretty significantly.

Simmons would also surely be Billups’ top option in the fastbreak/fullcourt offense, where he remains one of the most uniquely gifted transition players in NBA history. Assuming his free throw production levels off to around his career average, Simmons would surely receive a green light to attack the basket at will and would surely be the beneficiary of a few deep ball dimes from Dame Dolla.

Assuming his minutes are either significantly staggered with Jusuf Nurkic or the team opts to trade the former Denver Nugget for a better-fitting, 3-point shooting five, Simmons would likely have to set screens instead of being the beneficiary of them and would do the bulk of his halfcourt damage around the hoop deployed out of the dunker spot.

On paper, that seems like a relatively easy adjustment, right? Well, that might be easier said than done.

In 2020-21, Simmons only served as a roll man once every other game, recording only 23 possessions in the role over 1,877 total regular season minutes of action. Granted, it’s not like point guards are typically tasked with setting screens for other players all that often, but after playing 3,337 combined minutes on the court with Tobias Harris, Seth Curry, Shake Milton, and Tyrese Maxey, all of whom like to operate off of a screen, it’s pretty wild how infrequently Simmons was engaged in the two-man game once the ball left his hands.

Could Lillard and Simmons form a lethal pick-and-roll? Sure, I guess anything’s possible, but it’s just as likely that the former will see even more double-teams on offense, especially in the playoffs, where the Trail Blazers have long struggled. Even if Simmons puts his ego aside and becomes a willing screen-setter, his ability to turn the halfcourt offense into a 5-on-4 affair in the playoffs is just too tricky to ignore, especially on an ISO-heavy team like the Trail Blazers who don’t really have a secondary offensive option if CJ is back in the Keystone State.

I get playoff Lillard is a thing, but that hurdle may be too high to clear, even for him.

In the NBA, there’s nothing more dangerous than a desperate team. With the Portland Trail Blazers reportedly taking a bath on season tickets and the ownership group seemingly unwilling to sign off on even a godfather Damian Lillard trade offer, the chances of Joe Cronin making an eyebrow-raising deal to land a second legit All-Star increases with each compounding loss. If that happens, the Philadelphia 76ers may find themselves with a PP/KG-Boston Celtics-level trade offer, which might just be too sweet to ignore. Would Daryl Morey take advantage of said situation, secure some immediate contributors, and secure the firepower needed to exchange a player like Tobias Harris and a half-dozen first-round picks for a star player? Only time will tell, but in the interim, the on-court fit of Ben Simmons and Damian Lillard certainly wouldn’t be encouraging enough to be worth the sort of godfather offer needed to get a deal done, at least not in this writer’s humble opinion.