Since acquiring Jaylen Brown in a stunning blockbuster trade with the Boston Celtics on Wednesday night, the Sixers have agreed to deals with three free agents. 

Anfernee Simons, signed to a two-year, $12.3 million contract with a second-year player option, is the headliner. Then came two new two-way players, Rayan Rupert and Caleb Love. All three of them are former Portland Trail Blazers.

In an effort to learn more about all three players, PhillyVoice spoke with Sean Highkin, whose top-notch coverage of all things Portland basketball can be found at RoseGardenReport.com.

The following phone interview has been edited lightly for clarity and length:

Anfernee Simons

Adam Aaronson: Simons is a career 38.1 percent shooter on three-point attempts, but my perception has always been that he is a much better shooter than even that number indicates. Is that an accurate understanding?

Sean Highkin: I definitely think he's a better three-point shooter than that, and a lot of it is because, the last couple of years that he was in Portland after they traded Damian Lillard, he was really the main guy. He was the guy that other teams were game-planning for, so he drew double-teams every night, and that's going to bring your shooting percentage down.

On a team like the Sixers, where he is maybe one of their best shooters, teams that are doing the scouting, they're going to game-plan for Tyrese Maxey. They're going to game-plan for, if he's healthy, Joel Embiid. They're going to game-plan for VJ Edgecombe. Anfernee is probably going to be like sixth or seventh on the list of guys that teams think, ‘We really have to worry about that guy.’ So I think he's going to get a lot more open looks than he got his last couple of years in Portland.

He can get on some kind of crazy heaters. He has the ability to get on that type of heater and single-handedly win you a game. I think a spot like the Sixers is going to be good for him because he's going to come off the bench, he's going to just be asked to come in the game and get buckets, and that's going to be what he's able to do.

AA: The Sixers mostly used Edgecombe as their backup point guard last year, and there were growing pains, but it probably made him better off playing through some mistakes. I expect Simons to be a strong contender to back up Maxey this year. What do you make of his abilities as a playmaker and on-ball scorer?

SH: He got a lot better at that as the years went on, both that last year with Lillard… I think he's capable of doing both. I think that’s a good situation that they can have with VJ where they can still give him some of those reps and play Simons off the ball. Based on the Brown trade, the Sixers are obviously trying to contend, so they can only do so much of giving VJ the ball and have him be the point guard and letting him play through mistakes. It's hard to do that when you're trying to win. And so having a guy like Simons where, he’s not like an elite playmaker, but he's competent enough that he can step in and do that if they want to give VJ more off-ball reps. I could see that being a good pairing.

AA: What was Simons like as a teammate in Portland?

Simons is a pretty low-maintenance guy. He's not going to be complaining about his touches. He's going to just come in – he does his work. He's a good teammate. He's a good dude. It's a good culture fit and locker-room fit.

AA: If you want to nitpick this signing, you can point out that Simons is another small guard, and that he is regarded as a major weak link defensively. What have you seen from him as a defender?

It's not egregious, but just like any other small guard of that type. He's too small to be able to really stay in front of guys. If you ask him about it, he's somebody who will talk about how he cares about that being his perception, and he works on it, but it just hasn’t really happened. It just kind of is what it is with any player like that. But in a role like this, like what he's going to have with the Sixers, I don't think it's going to be as much of an issue as it maybe was the couple of years that he was here without Lillard, where he was the focal point and the Blazers had to play him 30-35 minutes a game and he wasn’t really guarding anybody.

AA: Is there anything else Sixers fans should know about Simons, either on or off the court?

SH: He won a Dunk Contest. He's got crazy athleticism, too. People think of him as a three-point shooter, but he's got pretty crazy bounce, too.

Rayan Rupert

AA: The first thing that stands out with Rupert is that he's 6-foot-7 with a 7-foot-3 wingspan. In three years in the league, with the tools that he has, what do you think has prevented him from putting it all together and being a quality rotation player?

SH: It's really the offense that's the issue. They kind of saw him as someone with the potential to be like Nicolas Batum – and that was like one of his mentors, childhood heroes, in France. And they have a relationship. But the Blazers saw him as that type of swingman, that type of 3-and-D, long wing that can hit a three. The shooting hasn't really come around. He's a career 32.4 percent three-point shooter. The shot has never really gotten consistent. They’ve tried to use him as a point forward and he turned the ball over a ton. The offense is really the thing. He's a super hard worker, super physically talented, it just hasn't really come together for him. I think the fact that he's going into year four and he's still getting a two-way contract and not a standard deal is kind of telling.

AA: Let's say Rupert finally does put it all together and becomes a quality NBA player. What does that look like? Is he a defensive-oriented wing and a somewhat reliable spot-up three-point shooter playing off the ball and defending multiple positions?

SH: A lot of the time that they put him in the G League, he was kind of running the offense. They were trying to use him as a point forward. He still was a little bit erratic as far as turning the ball over a lot. But if he can develop into that, then I think there's a spot for him. I consider him to be a Quadruple-A guy. I think he's too good for the G League, but so far it hasn't happened that he's developed into an actual rotation player on a team that's trying to win. He put up some good numbers last year in Memphis after he got cut by the Blazers and signed a two-way there, but the Grizzlies — their situation was their situation. Somebody had to put up numbers. So he got a good opportunity there to put up some numbers and stay on people's radars. But I think if he gets – after this fourth year on a two-way – if he gets another standard NBA contract, I think he would consider that a success.

AA: It does not seem like, at least as a defensive playmaker, Rupert has had the production one would envision given his length. What do you make of his overall defensive package?

SH: He’s got the size. It's just one of those things where a guy just hasn't put it together for whatever reason. He's got the size, he's got the IQ, he's a super hard worker. He's got all the intangibles. It just hasn't really worked out. I think part of it is just that he's never really had a consistent role and been asked to do stuff consistently – just because he was mostly competing for minutes with Toumani Camara, Deni Avdija, those types of guys. Especially the last couple of years when they weren't tanking, he wasn't really getting the reps of having to guard the best guys on other teams.

AA: What is Rupert like off the court? Is there anything else that Sixers fans should know about him?

SH: Great teammate, great guy. He's not like a super loud, talkative guy, but he's very thoughtful. Guys all really like him. His sister, Iliana, is in the WNBA, she plays for the Golden State Valkyries. Their dad, Thierry Rupert, never played in the NBA, but he was a legendary French national team basketball player. So they're like basketball royalty in France.

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Caleb Love

AA: Love shot 31.8 percent on threes, but I think that is also not reflective of the shooting talent he has. Is that fair?

SH: Well, he's just really, really streaky. He will get on these crazy heaters, and  he's one of these guys where, if you’re relying on him for a lot of minutes, he can win you a game or he can lose you a game. And he won the Blazers probably six or seven games in December and January when all of their other guards were out and he was basically their only healthy, functional point guard. When you sign a guy on a two-way, you don't expect him to play that kind of role, but with missing Scoot Henderson the first 50 games of the season, with Shaedon Sharpe missing some time, with Jrue Holiday missing a couple of months, they were kind of forced to rely on him.

They would not have made the playoffs last year without Caleb. But his efficiency numbers are not good, like 38.8 percent from the field, 31.8 percent from 3. And he's just really streaky. But I think on a two-way, with a team like the Sixers that have as many guards as they do, it's a totally fine two-way swing to take. And the thing about him, when you talk about small guards and defense, Caleb – anybody that small is going to be hard to be a good defender, but Caleb really competes on that end and he really annoys people. He’s not somebody who's going to just get out there and get buckets and not try on the other end. He competes on that end, at least.

AA: You mentioned him being a functional point guard. Should Sixers fans view him as a point guard or as more of a combo guard capable of playing on and off the ball?

SH: Ideally he's a combo guard, I think, because his main skills are scoring and shooting. He's fine as a point guard, as a passer, but that's not his elite skill. So I think in an ideal world, if he's going to get in there, then you want to have him playing with another point guard.

AA: Love takes tons of threes; he shot almost 14 of them per 100 possessions last year. But he also took more than 23 shots per 100 possessions. So there's a lot of two-point volume, too. Obviously, it's not particularly efficient yet. What do you sort of make of his scoring arsenal – or lack thereof – inside the arc?

SH: He'll get them up! He's a gunner, which, teams need that. It’s definitely something where there's a lot of development that needs to happen. But he's definitely not shy about shooting from anywhere.

AA: What is he like as a teammate? How did guys seem to respond to him in the locker room and how did the fans in Portland respond to him? 

SH: Phenomenal. He's A+ across the board in that regard. He had those games in December and January when they were so shorthanded that he basically won them all those games and all the guys on the team were really happy for him.

And the thing that I really respect about him is he had that middle stretch of the season where he played big minutes when so many guys were injured. And then around the All-Star break, they started running out of two-way days for him. That was right around the time that Jrue and Scoot and Matisse Thybulle and all of their other guards came back. And so he went from being a really important rotation guy for them and playing 20-plus minutes per game to not being in the rotation at all and not being on the active roster at all because they were trying to just conserve his two-way days.

It was really unfortunate that Love ran out of two-way days right when their other guards started getting healthy, so they didn't need him, and so they never ended up converting him. And he never complained once. He always had a really positive attitude. He was always like on the bench cheering for guys. He was always in the locker room joking around. He was never mad that he went from suddenly having a huge role to then just not having any. He always had the right attitude about it. He always stayed professional and stayed positive.

You really respect a guy that is able to have that perspective, especially because he was a decorated college player, but he knows what the deal is. He was undrafted, he signed a two-way, he had to grind to get his spot in the NBA. And so he understands that there are going to be times, especially on a team like the Blazers, that was trying to make the playoffs, that a two-way guy is probably not going to be playing if everybody's healthy. And he always had the right attitude about that. I was really impressed with how he handled that whole situation and his changing role as the season went on.

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