When NBA veteran Tree Rollins got a call from his old friend Brian Hill in the summer of 1993, the wheels started to turn. Hill was the new coach of the Orlando Magic, a team that included a young Shaquille O’Neal and Penny Hardaway. Hill wanted Rollins to come in as an assistant to work with O’Neal, specifically. The 7ft 1in Rollins, who had just come off two seasons with the Houston Rockets backing up Hakeem Olajuwon, contemplated the offer and after a few weeks accepted. For Rollins, in his late 30s, it was a great chance to start the second phase of his basketball life. Little did he know, however, what it would soon turn into.

“I went to Orlando to be an assistant coach,” Rollins tells the Guardian. “I would get out and practice with the team. With the big guy, Shaquille, you couldn’t stop him. But I could trick him, with my experience, and make him work harder.”

At the time, O’Neal, the reigning rookie of the year, was the most intriguing young player in the NBA. And Rollins, with his veteran savvy and calm demeanor, was the perfect person to help mold O’Neal’s raw talent. But a funny thing happened. “I’d do a better job of challenging him than our other backups,” Rollins says.

The other coaches would joke about it with the vet, how he should suit up again. But things got more serious when Magic management told Rollins they actually needed him to put on a uniform during a stretch of the season when the squad was paper thin due to injuries. Rollins’ first game was on 10 January 1994, against, of all teams, Houston. Upon playing in that contest, the veteran became the latest in an illustrious line of those who worked double-duty for an NBA franchise. Rollins was now a player-coach.

“I don’t know if I was nervous or afraid, I don’t know what I was,” says Rollins, remembering the moments ahead of the game against Houston. “But we got a contract worked out.” He pauses and laughs, “I should have held out.”

According to Rollins, who is the most recent NBA player-coach, fans thought it was a stunt by the Magic to sign him to play. But it was very real. In that first game, the Magic defeated Houston and Rollins totaled eight minutes, grabbed two rebounds and scored two points. He stayed on the playing roster for the entirety of the season and into the next. The one caveat for him as a player? “I didn’t do wind-sprints,” Rollins says. Players would joke that when it was time for the team to run, Rollins would “pick up the coaching book.” And after his two years on the Magic, in the summer of 1995, after the team had gone to the finals (Rollins’ first and only time), the NBA faced a lockout, which blocked management from communicating with players. “The joke was,” Rollins says, “I couldn’t talk to myself.”

The Georgia-born center, who first began to consider a career in coaching when he felt his “body winding down,” says it was originally Detroit assistant coach Brendan Malone (father of Nuggets champion coach Michael) who noticed he had a talent for it. Earlier, when Rollins was with the Atlanta Hawks, he befriended Hill, a scout at the time. Then when Hill got the head job with Orlando, it was a natural fit. Rollins, who stayed on as an assistant with the Magic through 1999, coached with several more NBA teams and later was a head coach in the WNBA. But to succeed, especially as a player-coach, required lots of work. Even though Hill said Rollins could relax on the coaching side of things once he signed on to play, Rollins couldn’t help himself.

“Me being me,” he says, “I continued to do all the assistant coaching duties.” Not only did he want to prove to the players and staff that he wasn’t coasting, but Rollins wanted to keep his coaching chops up, knowing that his playing days were winding down. So, he coordinated scouting reports before the games and wrote postgame reports after them. But the big man, who made the NBA’s all-defense team twice, experienced more hardship because of the job than just the rigors of the positions. While he strived to maintain good relationships with players and coaches, sometimes he was stuck in the middle of transactions.

“I’ve always been an easy guy to get along with,” Rollins says. “So, the toughest thing I had to deal with was very sensitive. As a coach, I knew if a player was about to be released – we’d talked about it in a meeting. But as a player, now I have to see him in the locker room, as his teammate. For me, that was the toughest thing with the whole ordeal.”

When a player is let go, it affects his livelihood and his family’s future. Those players facing that reality would at times get mad at Rollins, wanting a better heads up or to be fought for with management. So, Rollins found himself largely avoiding players he knew would be getting the axe. That aside, however, the job did have its perks. Rollins remembers fondly playing with O’Neal in games. “Twin towers,” he says. “I look back on that in my mind and I think, ‘Man, wow!’ I felt like a little kid playing with Shaquille O’Neal.”

But how did he succeed as a rookie coach who was still also playing? Well, Rollins, who says he never called a play for himself or checked himself into a game, credits his former mentors – a distinguished line of coaches, including Hubie Brown, Rudy Tomjanovich, Chuck Daly and Lenny Wilkens. Perhaps not coincidentally, the well-traveled Wilkens is also a former NBA player-coach. Other recognizable names who have been player-coaches include Bill Russell (the only player-coach to win an NBA championship in the role, doing it twice), Red Holzman, Dave DeBusschere, Dolph Schayes, Bob Pettit, Bob Cousy and Dave Cowens, who was the last player-head coach in 1978-79 with the Celtics at age 30.

As for Wilkens, he was a player-head coach for several years with the Seattle SuperSonics, later winning a ring in 1979 with the team as a full-time head man. A point guard known for his court vision and ability to set up players, Wilkens made a sublime choice for Seattle. As a freshman in college, he would sit behind the varsity head coach and “see what he saw.” As a pro, when the Sonics fired their head coach, the team’s general manager asked Wilkens to run the show. At first, Wilkens thought the guy was “crazy.” But it was so close to training camp at the time that he acquiesced. “I knew how to get the ball to people, knew who should have it,” Wilkens tells the Guardian. “That wasn’t a problem.”

For Wilkens, now the third-most winningest coach in NBA history, the transition from teammate to head coach was easier than expected. “The players were very responsive to me,” he says. “They trusted me. I knew how to run a practice, knew what we should be working on, how to help defensively. I knew that if I prepared and we did what we needed to, we were going to be successful. It really wasn’t complicated. I felt good in what I was doing and when the players responded positively, that made me feel even better.”

Hall of fame forward and former Olympic gold medalist, Spencer Haywood, who played in Seattle for two years under player-coach Wilkens, says the experience was “fucking great.” Wilkens, Haywood says, was able to correct mistakes on the court while also orchestrating the gameplan with the ball in his hand. Haywood says their chemistry and subtle signal calling on the floor led to many easy buckets. “You’re playing with a point guard that is an all-time great,” Haywood tells the Guardian of Wilkens. “And he’s breaking into coaching, and he’s an all-time great coach, too! I mean, what the fuck!”

In 1983-84, the NBA banned the player-head coach (though not the player-assistant coach) because, the argument went, head coaches don’t have caps on their salaries. Whereas players, who make much more than the coaches, do. (Though the Dallas Mavericks tried to circumvent the rule in the 2000s.) If someone was a player-head coach, then it could be a loophole to earn more money than he technically should. (The NFL and MLB use the same thought process today.) Despite this, many players today serve as de facto coaches on the court and in huddles. Steve Nash and Jason Kidd, both future coaches, had big voices as players with Phoenix and Dallas. Just last year, Marcus Smart led huddles as rookie head coach Joe Mazzulla and his staff watched. And all-timer LeBron James is even known for calling his own game-winning shots while holding a white board.

“It’s a sad thing to say,” says Rollins, whose 18-season playing career came to an end in 1995, on why there are no more player-coaches. “But it’s about the money.”

Rollins remembers playing for the Detroit Pistons around 1990. One day, the coaches ended practice early, but All-Star point guard Isiah Thomas said the team needed more work. So, while the coaches left, Thomas ran practice and worked his team out. This is a normal occurrence, Rollins says. Team leaders are often extensions of the coaches. But Rollins is old school – he was even the last player in the NBA to wear canvas Converse shoes. Today, he wants to see the position come back. And while Wilkens believes it would be “hard” to bring back the player-coach – some things, like canvas sneakers, may forever remain in the past – Rollins isn’t so sure. He’s keeping the door ajar.

“I’m sure some day they’ll find another way to bring the player-coach back,” Rollins says. “Look at that older guy in Miami [the recently retired 20-year veteran Udonis Haslam]. He don’t play. So, what is he doing? He’s being a mentor. They say he’s good in the locker room. So, I’m sure they are looking at a way to ease back into it – they’re going to find a way to bring it back.”