But as Philadelphia prepares to face off against Leonard and the Toronto Raptors on Saturday in Game 1 of the Eastern Conference semifinals, Sixers coach Brett Brown said the teams' prior meetings had no bearing on the future -- and that he expects Simmons to be up to the challenges that lie ahead.
"I think, and I understand the history of our lack of success is a real topic, but I would remind everybody we have never played them with the team we have," Brown said before his team practiced here Thursday afternoon, "so the context needs to be somewhat considered.
"In relation to Ben and Kawhi and all that, I think before our eyes, Ben rose ... his defensive effort in the Brooklyn series on D'Angelo [Russell] ... I don't know if he gets the credit ... I don't read much, but I don't know if he gets the credit he should and we hope to have some carryover on that.
"I think you're going to see multiple people, we have the ability to have multiple people guard Kawhi. So it would be wrong to assume that's his matchup for the series for sure he will be on him. But we have different candidates that we hope to show Kawhi different looks."
If Brown is wrong, and the prior three times Leonard and Simmons faced each other have any bearing on what happens in this series, Philadelphia will be in serious trouble. In those three games -- all Raptors wins -- Simmons averaged 13 points, 8.3 rebounds and 9.0 assists in over 37 minutes per game. More importantly, Simmons averaged an almost unfathomable eight turnovers per game.
Leonard, meanwhile, averaged 30.3 points, 7.7 rebounds, 2.7 assists, 4.0 steals and just 1.7 turnovers in over 34 minutes per game. The Sixers clearly hope things will look different when the teams start this series Saturday night at Toronto's Scotiabank Arena -- though Sixers guard J.J. Redick doesn't expect a drop-off from Leonard. Redick -- who spent several years with the Los Angeles Clippers, playing against Leonard when he was still with the Spurs -- said he thinks Leonard looks better now than he did before sitting out most of last season because of tendinopathy in his left quad and ultimately being traded to Toronto last summer.
"I think he looks better, doesn't he?" Redick asked. "I think he looks better. He looks better. He's pretty damn good."
Leonard certainly lived up to that billing in Toronto's five-game series victory over the Orlando Magic in the first round, scoring 27.8 points per game while shooting 55.6 percent from the floor and 53.8 percent from 3-point range as Toronto bounced back from losing the opening game by winning the following four to close out the series in five games -- just as the Sixers did against the Brooklyn Nets.
"I think they're totally different basketball teams," Redick said, when asked to compare Brooklyn and Toronto. Obviously [the Raptors] have a go-to guy. At times in the Orlando series it seemed like two go-to guys in Kawhi and [Pascal] Siakam. Kawhi is a bonafide superstar in this league and there are only a handful of those guys spread over 30 teams, much less 16 in the playoffs, so it starts with him right there."
Still, the Sixers have one of those players, as well, in Joel Embiid -- not to mention Simmons, Redick, Tobias Harris and Jimmy Butler, all of whom combine to form one of the most talented starting lineups in the entire NBA.
It was one thing for Philadelphia to push its way past Brooklyn -- especially considering the Nets' lack of size inside allowed Embiid to absolutely dominate despite ongoing knee issues that limited both his movement and conditioning. It is an entirely different thing to try knocking off the Raptors, who won 58 games this season despite having Leonard and Kyle Lowry combine to miss 39 games.
"We did our job the last four games. But knock on wood," Butler said, as he stomped his foot on the hardwood floor of Philadelphia's practice gym for emphasis, "I don't want this to happen, but what if we lose the next one? What will the question be then? Are we playing like s--- now?
"Basketball is a game of runs. Stuff happens."
Philadelphia was prone to giving up those runs to Toronto in the three games the Sixers played against the Raptors when Leonard was in the lineup (Philadelphia won the other meeting handily). Much of the reason for that was because of those turnovers that Simmons committed -- and Leonard helped create.
But both teams have undergone radical transformations since the last time they met each other Feb. 5. The Sixers traded for Harris, Mike Scott, Boban Marjanovic, James Ennis and Jonathon Simmons, while Toronto traded for Marc Gasol.
Philadelphia has spent the last two months trying to incorporate all those pieces despite only having them on the court for a limited amount of time. Including the first round, Philadelphia's starters have played together in a grand total of 14 games. The Sixers are hoping that, despite that ongoing lack of familiarity, they can leverage their significant amount of talent to knock off the Raptors and advance to the Eastern Conference finals for the first time since 2001 -- also the last time Philadelphia made the NBA Finals.
"I mean I think we just have more firepower and experience," Brown said of where his team stood after the trades. "What we don't have is the consistency of familiarity. We are going up there with a pretty impressive starting five that we all talk about, and the only downfall to that and it has to be considered, is you're playing against a team that has been with each other for the majority of the year, and [has] acquisitions like Marc Gasol coming in is their little boomerang in the flow of what was an annual group. Kawhi and so on.
"We don't have that. We do not have that. But what we do have is firepower."
One part of that firepower that could be compromised is Scott, who has emerged as Philadelphia's most reliable bench piece -- including hitting the game-winning shot in the closing seconds of Game 4 of the first round series against Brooklyn. Scott was listed as out of practice with a bruised right heel Thursday, as well as dealing with plantar fasciitis in his right foot, and Brown said he isn't expecting Scott to be available to play.
"No, I'm not," Brown said, when asked if he was planning for Scott to be available.
"If we do, it's a blessing."