4 ways the Raptors could trade for 76ers star Ben Simmons

The Ringer's Kevin O'Connor explains whether the Toronto Raptors are a fit for Ben Simmons and what it might take to get him.

Though it took longer than most might’ve expected, on Tuesday the wheels began to get set in motion for Ben Simmons’ inevitable departure from the Philadelphia 76ers.

After a devastating seven-game loss in the second round to the Atlanta Hawks that saw Simmons largely falter, and finish Game 7 with the awful lasting image of him passing up an open dunk, Philadelphia looks to be making their move to move the soon-to-be-25-year-old three-time all-star and two-time all-defensive first team selection.

First reported by The Athletic’s Shams Charania, the asking price for Simmons isn't cheap as the 76ers are looking for an all-star calibre player in return. The kind of all-star player, according to longtime NBA insider Marc Stein, that Philadelphia president Daryl Morey is looking to get for Simmons would be a Damian Lillard or a Bradley Beal.

Of interest to Toronto Raptors fans, however, is Stein reporting that Toronto has been said “to have expressed interest” in Simmons.

For all his flaws as an unwilling -- and just plain bad -- shooter, Simmons is still a very young three-time all-star who has become one of the game’s best defenders, and is one of the game’s most unique talents as he’s, essentially, a six-foot-10 point guard who can pass and play make with some of the best in the league.

As unlikely as it might seem right now, with the Raptors-Simmons connection levied out there by Stein, we decided to take a look at four possible trade scenarios for Simmons.

Sign-and-trade Lowry for Simmons

In the NBA you can pull off a transaction called a “sign-and-trade,” where a team is able to re-sign one of its free agents for the purpose of trading that player to another team.

In the Raptors’ case, they have a massive free agent in Kyle Lowry who, despite being 35, could command major money again -- especially given what Chris Paul is doing at 36 years of age in the NBA Finals right now.

Conveniently, for a hypothetical deal with the Sixers, if the Raptors decide to re-sign Lowry at the same figure as this past season ($30.5 million), that would work well as far as salary matching goes for Simmons, who is owed about $33 million next season and about $146.68 million over the next four seasons.

In terms of fit for both teams, while the Sixers have been said to covet the Philadelphia native Lowry for a while, it’s unclear if they’d want to bring him in at about $30 million per season. If that is the case, the number would have to be lower, which might complicate the transaction on the Raptors’ end a little more.

With that said, Lowry would look great on Philly’s roster as a legitimate playmaker who makes others around him better, a plus-defender and -- most importantly -- a deadeye shooter that would help better space the floor for the likes of Joel Embiid and Tobias Harris.

As for the Raptors, given the success they've had with Fred VanVleet playing off-ball as a shooting guard alongside Lowry, they could keep that strategy intact because Simmons could slide in as the team’s starting point guard, alongside VanVleet in the backcourt.

His shooting woes would be problematic, but the possibilities defensively of a starting lineup that features a foursome of Simmons, VanVleet, OG Anunoby and Pascal Siakam would be intriguing to say the least, and could mitigate the lack of outside marksmanship.

Toronto Raptors forward Pascal Siakam, left, tries to get past Philadelphia 76ers guard Ben Simmons. (Matt Slocum/AP)

Trade Siakam for Simmons

Of all the scenarios we’ve included here, this feels like the least likely, but it’s still an option. This would be the easiest one-for-one swap to make happen as both Simmons and Siakam signed the exact same max rookie contract extensions back in 2019, with the only exception being Simmons going for five years of term instead of Siakam’s four years.

A swap with these two players involved would basically be for the exact same money so the trade would be easy to make.

In terms of fit, however, it's less simple. From a Philly standpoint, Siakam wouldn’t be great for them. Where he likes to do damage (from the wings and in the post) are the exact same spots Harris and Embiid operate from, meaning spacing might be problematic.

As for the Raptors, the benefits of having Simmons would be mitigated because Siakam is the team’s best offensive weapon, and you’d want to pair Simmons with Siakam in what could be an interesting pick-and-roll combination -- creating a tandem in which either could conceivably play the passer or the roll man.

The biggest thing that would hold this deal back, though, is Siakam’s injured shoulder. Though he’s is expected to be back by about November or December, odds are the Sixers want to bring in an all-star calibre player without any injury concerns to speak of.

Toronto Raptors guard Fred VanVleet, pictured above. (Ashley Landis/AP)

Trade VanVleet for Simmons

A popular trade idea, the benefits for the 76ers are obvious and similar to that of Lowry. VanVleet is a plus-defender and a great shooter, but from Toronto’s perspective this specific transaction is a bit problematic.

First off, the trade would have to be more complicated as VanVleet is set to make about $19.67 million next season, so more players and money would have to be involved.

For argument’s sake, though, let’s assume the money is able to work. The next issue is that if the Raptors were to make this move they’d basically have to re-sign Lowry, which isn’t a bad thing, but could be difficult as he’s an unrestricted free agent and could be looking to move on to another team.

It’s absolutely vital that Simmons would have a great shooter with him in the Toronto backcourt to compensate for his poor shooting ability, which is why you’d want to bring Lowry back. Of course, with the No. 4 pick, the Raptors could select a guard like Jalen Suggs or Jalen Green and they could start immediately. But banking on a rookie -- no matter how talented looking -- is a big risk if you go for a win-now move like trading for Simmons.

Lastly, let’s say the Raptors do manage to retain Lowry and make this move for Simmons. There’s still a chance it wouldn’t be a good fit because, with Lowry, the Raptors already have a supreme playmaker and while having two isn’t exactly a bad thing, both Lowry and Simmons need the ball in their hands to make each of their own special kinds of magic work.

It just feels like there’s too many red flags to make a VanVleet-for-Simmons deal worth it.

Utilize the No. 4 pick to get in on a deal for Simmons

Last but not least, there’s the scenario of actually using that No. 4 pick as a trade chip.

This is a strong draft this year, so that No. 4 pick has some serious value -- perhaps enough to allow the Raptors get into a three-team deal along with the Sixers and the Portland Trail Blazers or Washington Wizards, where the Raptors send the pick in exchange for Simmons while Philly lands one of Lillard or Beal.

It’s a bit of a farfetched idea, but this is the NBA and where there’s a will there’s always a way, so don't discount it entirely.

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