Anfernee Simons isn’t allowed to try his most impressive shot in an NBA game. It’s a form of basketball sorcery few can process, let alone immediately master, that first emerged when he was a senior at Edgewater High School playing H-O-R-S-E against his head coach Jason Atherton.

The two challenged each other after practice and during gym class. H-O-R-S-E provided an opportunity for Simons to test himself by showing off a bold menu of trick shots, while placating a competitive spirit that turned every contest into a life-or-death event.

Dunks weren’t allowed, so Simons dealt letters with his limitless range, firing from the overlapping volleyball court that approximated an NBA three, or behind an arbitrary black line drawn nearly 40 feet from the rim. (Simons later asked Atherton, if he could shoot it during a game. “I told him if I call out ‘Black’, go ahead and fire it,” Atherton says. The coach finally granted permission on senior night.)

Simons enjoyed exploring his own limitations, which remain untapped. This is how The Shot was born. Imagine the deepest corner three possible, tucked a couple feet behind the NBA’s line. Now step over the baseline, out of bounds and behind the backboard. Impossible, right? Simons calls it his “safe shot.” Basic geometry politely disagrees.

The first time Atherton saw it, he wondered if Simons had secretly spent hours practicing on his own time. Nope. It was improvised.

Simons made the shot on his first try, then again when Atherton dared him to repeat it. According to his coach, in all the games they played together Simons drilled this exact shot at an 80 percent clip. “The first couple times I shot it, I’m like ‘I don’t know how the hell you’re doing this!” Atherton laughs. “He’s comfortable no matter where he is.”

Back then, Simons was a prodigious teenage question mark who barely weighed 160 pounds. Today, he’s a 20-year-old wildfire of natural talent entering his second season with the Portland Trail Blazers. It’s a season prefaced by towering expectations. As a rookie, Simons gave the team several reasons to be excited. But it’s his innate ability to make a complicated game look like a cakewalk that separates him from so many other young guards.

“The thing I’m most excited about is how easily the game comes to him,” Blazers general manager Neil Olshey says. “It’s very hard to put guys on the court that can’t score, and it’s something that comes very natural for him. It’s easy for him.”

Everything about him is casual, but Simons meets challenges imposed by coaches, opposing players, parents, and especially himself, with the restlessness of a master chef restricted to boiling hot dogs. “Some of the shots that are tough shots, he doesn’t make them look tough,” Trail Blazers head coach Terry Stotts says. “When he drives in the lane, there’s just an easiness to it.”

Simons can score at the rim, from mid-range, and behind the three-point line, but his outside shot is his calling card. It starts with wrists that make opponents feel like reality is in fast forward. One second, the defenders are crouched in a sound stance, arms out, feet staggered, and jumpy. The next, they’re yolk in a skillet.

“When I was young I’d just push the ball up. It was one motion,” Simons says, describing his unique jumper. “Usually when guys get older they make it two motions, so I kind of kept it as one motion and it’s still working out.”

Simons’ skillset is lined with cashmere. He says he models his game after Jamal Crawford, with a hint of teammate Damian Lillard’s aggressive mindset. Justin Zormelo, a private skills trainer who works with Simons, says Lillard is a fair comparison, but also recognizes Klay Thompson’s sense of calm. “I think if you combined [Dame and Klay] that’s who he is,” Zormelo says. “A rough draft copy of those two guys.”

The Blazers knew it’d be hard for any rookie to crack their rotation in 2019. They finished the previous season with 49 wins and one of the league’s deepest, most expensive rosters. “Risk tolerant” was how they viewed their draft strategy. Selected with the No. 24 pick in the 2018 NBA Draft, Simons only played 141 minutes during his entire rookie season, patiently waiting for garbage time to show what he could do while Lillard, CJ McCollum, and Jusuf Nurkic lifted the Blazers to another No. 3 seed.

“I think when his career is over, they’re all gonna say, ‘Where was he picked?!’” -Rick Pitino

Riding the bench wasn’t easy, but Olshey constantly reminded Simons he was a lottery talent who didn’t play for a lottery team. The opportunity to learn from one of the league’s best backcourts would pay dividends in the future.

“One of the things Dame and I talk to him about is his pace. I always tell him ‘You don’t have to go 100. Find your 80, find your 75 at first, and then progressively speed it up’,” McCollum says. “He’s got the total package, man. He’s 20 years old, not even old enough to drink.”

Olshey recently called Simons the most gifted player he’s ever drafted, a list that includes Lillard, McCollum, Blake Griffin, and several more notable names.

“He is not currently the best basketball player I drafted. He’s not the most functional player that I drafted at the time of the draft,” Olshey says. “But just in terms of his natural gifts at his age, and his God-given talent, it rivals anybody else that I’ve drafted in my career. Now, I don’t know if he’ll reach that ceiling as a player and put it all together, but the things that you basically can’t teach, in terms of just intrinsic talent, he has.”

With one of the highest payrolls in the league, the Blazers need low-cost production to elevate their established starpower. That not only makes Simons one of the most important people in the organization, but, given how open the league’s title race appears to be, he’s also one of the most essential young players in the entire NBA.

How soon can Simons bloom into the necessary source of internal growth the Blazers need to achieve their ultimate goal? Is he their golden ticket, or a tantalizing project that can’t live up to expectations? That development is caked into their short-term future as much as the long haul.

It’s an early July morning in Las Vegas as Simons sits on a beige couch in the Four Seasons lobby. A matted flat-top adds five or six inches to his willowy 6’3 frame. He leans forward and folds his arms.

Those who know Simons sum up his personality with words like “shy” or “extremely quiet,” followed by “humble” and “polite.” They’re not wrong. Minus the retro concords and baby face, he could pass for a member of the Queen’s Guard. Limp eyelids rest above lips that don’t budge unless they must, and when they do, his voice carries only a brief hush. No handlers, coaches, trainers, brothers, sisters, cousins, teammates, childhood friends, or agents stand to the side. Instead, Simons is escorted into the lobby by his parents.

“If you didn’t know who Anfernee was, you’d have no idea that he’s one of the best basketball players in the world,” Atherton says. “That’s just kind of how he carries himself.”

Early last season, McCollum was tired of seeing Simons and fellow Blazers rookie Gary Trent Jr. wear cut-up jeans to games. He arranged for Antar Levar, McCollum’s clothier, to measure them for custom suits. Simons eventually settled on blue, gray, and glen plaid super 130’s from Cacciopoli, but the process wasn’t easy. Levar, who works with nearly 150 professional athletes and celebrities, was caught off guard by Simons’ extreme reticence.

“It was like pulling teeth out of a baby trying to get him to speak!” Levar laughs. “When I would show him stuff, he would barely be like yes or no. He’d be real subtle, real quiet, like ‘Nah, nah, nah,’ and then he’d say ‘Yeah, I like that. Nah, nah, nah.’’ It was real quick, and I was like, man, this guy, he’s not gonna say nothing!”

McCollum chuckles telling his version of the story: “Like they say, you’ve got two eyes, two ears, and one mouth for a reason.”

The Player Empowerment Era is wrapped inside a generation defined by self-promotion, but Simons is unassuming in a way that’s far from performative. He seems uncomfortable answering questions about himself, unsure how much to reveal or whether any of it is actually interesting. He doesn’t watch League Pass “unless there’s a good game on.” He’s content with a monotonous life pervaded by Marvel movies (Captain America: Civil War is his favorite), and video games.

Simons understands the importance of making new connections, but opening up takes time. Before his professional career began, Simons’ father Charles couldn’t remember seeing him chat and laugh with teammates on the bench. “He’s not a talker by nature,” Charles Simons says.

Perennial silence is not a deal breaker for NBA stars (see Leonard, Kawhi), but coaches throughout Simons’ life have tried to draw him out of his shell with unique leadership opportunities. At IMG Academy, where Simons spent a post-graduate year after high school, he handled the ball in critical situations and also collected his teammate’s uniforms after games. Even after he broke his hand in early October, Simons still participated in every conditioning exercise instructed by the coaching staff. Whether it was a grueling suicide drill or a simple down-and-back, he obsessed over finishing first and setting an example.

“We put him in positions where he has to deal with people, step up, and hold himself accountable,” IMG Academy’s post-grad head coach John Rhodes says. “You have to start with yourself before you can get others to follow, right?”

Portland’s staff grabbed the baton. The Blazers made Simons their starting Summer League point guard for several developmental reasons, one being it forced him to deal with teammates in ways he hasn’t before. “I still want him to be more assertive and more vocal,” Blazers assistant coach Jim Moran told reporters in Las Vegas. “Running the team, he needs to be more communicative.”

Simons agrees. “I’m used to not saying anything on the court,” he says. “Now it’s more, you’re running the team. You need to make sure everybody is in the same boat.”

Born in a suburb just north of Orlando and named after Magic icon Anfernee “Penny” Hardaway — as a fellow Tennessean, Charles was a fan — Simons could breeze through traffic cones with a live dribble by the time he was five. A family friend who coached one of Florida’s most prominent AAU teams worked him through basic drills. Simons shot on 10-foot rims and always used a regulation-sized NBA ball.

When organized games began two years later, referees allowed the kids to commit violations without penalty. Dribbling was optional for everyone … except Simons. “I was the dad that never let him play like a little kid,” Charles laughs.

Entering his freshman season at Edgewater High School, Simons was a 5’8, 130-pound, 13-year-old paper clip. Continuing a habit that began in the park eight years earlier, he spent two hours after the varsity team’s practice working on his game, and would constantly pester Atherton about the gym’s availability.

As a way to let his frail body catch up to a budding skillset, Simons reclassified down to the 2018 class after his sophomore year. He had spent most of his minutes playing off the ball, and opponents took advantage of his size on defense. Heading into his junior year, Montverde Academy, the same program D’Angelo Russell and Ben Simmons attended in prior years, had an open spot on their team. Simons was at first hesitant to transfer, but his parents encouraged him to step outside his comfort zone.

Montverde wasn’t a perfect fit. His playing time fluctuated, and the 40-minute commute from his parent’s home to campus was inconvenient when practices required a 3 a.m. wakeup call. But the experience had immense value. Simons himself detected immediate growth, and others now say Montverde was a pivot point in his trajectory.

“I just think it helped him understand that he played on a team with a lot of really good players,” Montverde associate head coach Rae Miller says. “Practices at our place are usually much harder than games because it’s so competitive.”

Simons re-enrolled at Edgewater the following season, three inches taller and the owner of previously unthinkable athleticism. By then, he was heavily recruited by several programs, including Louisville. Rick Pitino, the school’s former head coach, personally attended every one of Simons’ AAU games, scouting him with the same attention he gave Donovan Mitchell and Terry Rozier.

“I told the assistant coaches, ‘I’m recruiting Anfernee. He’s my guy,’” Pitino says. “I said ‘I’ll take care of him, you take care of the other guys.’ He’s done some things dunking the basketball, my mouth was open when I saw him do it.”

Simons committed to Louisville in the fall of 2016, but plans fell through when an NCAA corruption scandal led to Pitino’s termination soon after. In an effort to bulk up before his freshman season at another school, he pivoted to a post-grad year at IMG Academy, where first-class strength training facilities and a helpful nutrition program allowed Simons to get stronger. (Also, it’s where Penny Hardaway’s son Jayden became Simons’ teammate.)

At IMG, Simons put mesmerizing performances on film. A sky-high ceiling helped him become the first American-born player since 2005 to enter the NBA without first competing overseas or in the NCAA. During a lengthy phone conversation with Olshey before the draft, Pitino repeatedly referred to Simons as a steal who’d eventually make whoever selects him look like a genius. “I think when his career is over, they’re all gonna say, ‘Where was he picked?’,” Pitino says.

The first time Zormelo worked with Simons, he told him things few 18 year olds ever hear: You can make all-star teams. You should score 40 in an NBA game. When a team gives you the green light, 50 points will be an expectation.

At the time, Simons had knee tendinitis and couldn’t work out any longer than 30 minutes without limping. In addition to bringing in a specialist who helped build up his quad and alleviate the pain, Zormelo had Simons train against G League players. At first, their physicality and strength was too much. One week later he made the rim look wider than a manhole cover. “Those guys couldn’t guard him,” Zormelo says. “Nobody could guard him.”

A few months after, Simons held private pre-draft workouts in front of about 20 NBA teams. Wanting to silence any doubt about Simons’ body and game, Zormelo made a risky and unusual decision to put live defenders on him before every drill. “He was unconscious for three days,” says Zormelo, who’s trained Kevin Durant, Paul George, and myriad other NBA stars. “He had some of the best workouts I’d ever done, or ever seen.”

A few teams thought about taking Simons in the lottery. Even though his potential was Eddie Murphy circa 1979 — at one point he was a top-five pick in ESPN’s 2019 mock draft, right behind Zion Williamson, and R.J. Barrett — none would commit to a prospect who required such a long runway. Portland embraced the uncertainty and was confident he’d make headway on a timeline that didn’t force any immediate pressure on his narrow shoulders.

An early step toward vindication came in the first start of his career, which was also the last game of the 2018-19 regular season. With Portland’s key rotation players sitting out to prepare for the postseason, Simons scored 37 points to lead the Blazers back from a 25-point halftime deficit against the Sacramento Kings. It was a feat of technical excellence that was almost immediately overshadowed by an underlying message: This dude belongs.

In the process, Simons became the third teenager in NBA history to tally at least 37 points and nine assists in a game, the first two being LeBron James and Kevin Durant. Filter out assists, and Carmelo Anthony is the only addition to that list.

After the final buzzer, Olshey grabbed Simons in the locker room. Do you understand what you just did? The rhetorical question had an answer. Without a second of rest for 48 minutes, Simons locked Portland into the No. 3 seed.

That eventually bestowed an appreciative public with Lillard’s epic step-back over Paul George in Round 1 and McCollum’s status-elevating Game 7 against the Denver Nuggets in Round 2. All of that was lost on Simons, who only remembers how it felt to flow without worry, knowing the Blazers made only seven healthy players available.

“The innocence with which he looked at me,” Olshey says. “He was just excited to finally get an opportunity and play unfettered and not look over his shoulder.”

Simons continued to back up the hype at his second Las Vegas Summer League. He put the entire offensive package on display: cotton-ball floaters, step-back 25-footers, and coast-to-coast urgency with a lit-fuse live dribble. In his third game, as dozens of general managers, coaches, scouts, and executives across the NBA looked on, Simons carved up the Jazz for a Summer League-high 35 points. He left Las Vegas with an absurd 71.6 True Shooting percentage, 30.5 usage rate, and a spot on the Summer League’s All-Second team.

The Blazers view this tangible growth as a key to their future. By letting backup guard Seth Curry sign with Dallas and trading Evan Turner (who held the ball for more minutes than McCollum last season) to Atlanta for wing Kent Bazemore, Olshey purposefully cleared a path for Simons to contribute this season.

Zoom out and Portland’s rotation is volatile. For the first time since 2016, the Blazers will not start the year retaining more than 82 percent of the previous season’s minutes on their roster. No team in the league had more continuity over that stretch. “I think if we didn’t believe Anfernee was ready to step into that role then I would’ve played it safe and brought in a veteran,” Olshey says.

It’s easy to imagine scenarios where Simons breaks through to deliver moments that will foreshadow his staying power. The Blazers have successfully deployed three-guard units in the past and will use Simons, Lillard, and McCollum at the same time.

“I think with Anfernee’s size and athleticism and Dame’s ability to guard bigger players, that’s going to be a unique lineup for us,” Olshey says. Stotts also likes to platoon his starting backcourt, which will allow Simons to function as a more prominent weapon while one of Portland’s star guards gets some rest.

The Blazers are optimistic Simons will follow the blueprint laid out by McCollum, another combo guard whose shot options are “all of the above” at any given time. Like Simons, McCollum barely contributed as a rookie. By his third year, McCollum’s scoring average eclipsed 20 points per game. One difference: McCollum was 22 years old when he debuted, while Simons doesn’t turn 21 until next June.

“I would’ve been a lot more immature than he was at that age. He listens well, he works extremely hard and I think he got more comfortable as the year went on,” McCollum says. “I’m sure he feels like this is a chance for him to get some minutes and I’m sure the organization is looking at his performance, his development, and trying to figure out when that time is. It may very well be this season.”

Simons doesn’t know what his exact role will be this year, but he expects more responsibility. Scoring is obvious, but his ability to defend opposing backcourts while running the team’s offense is a mystery. “He’ll have opportunities,” Stotts says. “And he’ll grow with those opportunities.”

Of course, expectations don’t always align with progress, so the Blazers will adjust if Simons fails to take a meaningful step forward. “We have other alternatives on nights where he’s gonna struggle,” Olshey says. “Or he’s up against matchups that he’s just not ready to handle yet.

But Simons is also the most exciting archetype in sports: an ascending phenom who is now positioned to make the most of his natural ability. He can be the explosive supplement Portland didn’t have in the past.

The best-case, short-term scenario is that Simons alleviates the scoring burden Lillard and McCollum have carried by themselves. Whether he lets those two stars operate more off the ball — Portland is high on Simons’ “game sense,” aka the ability to initiate their offense — weaves around screens himself, or isolates on the wing, defenders can’t ignore him. On paper, that could make the team’s offense unguardable.

The Blazers are experienced enough not to crumble if Simons can’t handle his new duties, but it’s hard to see them winning it all during this era unless he soars. Based on a lifetime’s worth of evidence, that shouldn’t be a problem. Becoming a meaningful contributor is a challenge Simons knows he’ll conquer sooner rather than later. Just like a game of H-O-R-S-E.