The Shades of Ronnie DeGray III

On Oct. 21, 2017, fresh off an unofficial visit to Kansas State, Ronnie DeGray III capped off a busy day with a little bit of light snooping. The rising high school junior wasn’t the only prospect in town. Throughout the day, Kevin McCullar, another sturdy wing, also watched the Wildcats roll to a 16-point exhibition victory over Missouri State, toured the program’s facilities, and squeezed in a FaceTime chat with coach Bruce Weber.

That autumn Saturday wasn’t the first time DeGray and McCullar crossed paths. As the day wore on, though, DeGray kept thinking back to summer, when the recruits faced off on Adidas’ grassroots circuit. “I felt I had outplayed him, too,” DeGray said. Yet, there was one metric where McCullar owned a decisive edge: scholarship offers.

DeGray, then a still-lean 6-foot-6 prospect, only had one to his name: Denver, a modest program out the Summit League and 20 minutes from his family’s home in Parker, Colorado. That fall, however, it looked as if they might change. A week earlier, DeGray jetted east to visit Pitt. Two weeks later, his itinerary had him slated to visit Missouri.

But that night in Manhattan, Kansas, DeGray opened an internet browser and looked up McCullar’s recruiting profile. Scrolling through the list, DeGray’s envy mixed with frustration. “He had everyone you could think of,” he recalled. “I wanted to be in that predicament.”

Instead, DeGray returned from each trip empty-handed. A stellar junior season for Chaparral High School, where he averaged 21 points per game, didn’t prove compelling. And no high-major suitors were moved by a grassroots season where DeGray’s output and efficiency put him on par with top-150 talent.

Back then, DeGray possessed a multi-positional tool kit that recruiters claim they covet: a wing capable of drilling corner 3-balls, burying smaller guards after switching in the post, driving on slower-footed bigs from the elbow, or bolting backdoor when a defender overplayed. In a pinch, he could handle the ball against the press. And even as a high school freshman, he could quickly process the action in front of him and anticipate defensively.

Yet each time Tellus Truesdale, Chaparral’s coach, rang up power-conference assistants, the feedback was the same. “There was never a question about Ronnie’s skill level, his numbers or work ethic,” Truesdale said. “It was just that he’s not a big man, and he’s not classically a guard.”

DeGray’s plight is a familiar one. Like other positionally ambiguous prospects, reaching his desired destination required time and a circuitous path. For DeGray, it wound through New England, with two years at a prep school and disrupted freshman season at UMass. This spring, DeGray – along with 1,500 of his peers – bet on himself again by entering the transfer portal.

Today, the versatility that once defied easy categorization is the chief selling point. Prowling the transfer market, Cuonzo Martin’s hunted for skill: Amari Davis’ pull-up game, DaJuan Gordon’s slashing ability, and Jarron Coleman’s shooting and vision. In landing DeGray, who committed two weeks ago, the fifth-year coach might have acquired a hybrid forward to help his pace-and-space evolution take another step.

“College basketball is a business,” DeGray said. “It’s just worked out in a funny way where I’m able to be part of this program for the next couple of years.”

Last Fall, UMass coach Matt McCall spent almost 40 minutes moving magnets around a board, delivering a virtual tutorial on the Minutemen’s spread pick-and-roll attack. But before delving into the nuances of the continuity-based system, the 39-year-old, who picked up his diagramming habit working alongside Florida legend Billy Donovan, briefly fleshed out the traits required to make the up-tempo system whir.

“When you look at your roster, what kind of front-court players do you have?” McCall told the coaches tuning in. “Are your front-court players shooters? Do you have guys that can pass? That’s a huge thing if you’re trying to run spread pick-and-roll and space the floor.”

Fortunately, McCall already had one at his disposal. Tre Mitchell, the reigning Atlantic-10 Rookie of the Year, remained in the fold after an offseason that saw the program endure a nine-player exodus. What McCall required was a complementary piece alongside his star. Given the churn in Amherst, he surveyed a roster ranked 332nd nationally in experience, according to KenPom. In short order, though, a viable option emerged — DeGray.

At its core, the Minutemen’s offense relies on a pattern, a rolling conveyor belt churning out of side ball-screens. A combo forward must be comfortable popping out on the wing, slipping to the corner, rolling hard to the rim, or ducking into the lane for a high-low feed.

“The four makes a lot more decisions with the ball,” said DeGray, who started all but one game and averaged 8.7 points and 4.6 rebounds. “Most of my touches came at the top of the key. But if they ran a specific play for me, it was usually on the right block.”

The ease of DeGray’s acclimation might seem remarkable under the circumstances. Like every program, UMass navigated an offseason program disrupted by the unfolding COVID pandemic. Worse, an outbreak within the program wiped out the first three weeks of the Minutemen’s non-conference play — the first of three stoppages for that plagued last season.

It’s not surprising if you know DeGray’s developmental background. Picking up the beat in a system reliant on reads and rhythm started when he was a high school freshman.

Back in 2015, Truesdale ushered in a similar youth movement. A talented crop of freshmen, including DeGray, opted to enroll together at Chaparral. Early that preseason, the coaching staff hoped the specter of newcomers stealing minutes might spur buy-in from upperclassmen. They dumped the carrot-and-stick approach after DeGray, then a lean 6-foot-6, Bryce Matthews and Joe Dalton held their own in a preseason jamboree.

“After a game or two,” Truesdale said, “it was like, ‘alright, guess we’re going to start them, too.’”

DeGray’s frame fit proper proportions, but he lacked strength and bounce. “When he dunked, it was a baby dunk,” Truesdale added. What he did have was a mind equipped with fast processing power. DeGray quickly recognized actions and became a stellar off-ball defender. “You don’t usually see big guys sliding their feet and taking charges,” Truesdale recalled. “They’re always trying to block shots.”

Still, the season’s modest outcome – a 9-16 record – was what you’d expect. Easing youngsters into heavy minutes demanded compromises, and Chaparral stripped its offense down to the studs. Yet those schematic bare necessities cultivated the core skill set that makes DeGray a potentially intriguing piece.

Truesdale installed a read-and-react system developed by Rick Torbett. But instead of lead guard deciphering options, four off-ball players — called reactors — make two-man reads. The offense is made up of 17 layers, with teams progressing as they master each one. Over time, reads become so ingrained they’re practically instinct.

The direction a ball-handler takes dictates which direction off-ball players rotate in a circular pattern — a middle drive yields these options: a shooter drifting to the corner, another filling behind, and a cutter running the baseline. What if the man bringing the ball up passes? Easy. On a ball reversal, they cut hard to the rim, circulating back out to the corner. If they’re held up, they veer and set a screen in the slot for a teammate who curls over the top.

Meanwhile, big men sink to the short corner or lift to the elbow based on the direction of a drive. And the system also builds in ways for them to post-pin for high-low feeds or receive rip screens to post up.

The Wolverines built their offense on that platform over the next two seasons, a progression paralleling DeGray’s physical maturation. Eventually, he came to favor left-handed drives from the wing, even though he was a natural righty, and became adept at exploiting defenders denying him on the perimeter.

“He’s a smart guy, and there would times when he takes a step toward the ball and goes backdoor,” Truesdale said. “Depending on the direction of help, he’s either finishing or kicking out.

The read-and-react was also flexible enough that Truesdale could tweak his alignments, toggling between twin-post or four-out look, based on the opponent. Doing so meant fleshing DeGray’s back-to-the-basket game. “Just a few moves and footwork working toward a baby hook,” Truesdale said. “If he’s catching the ball outside the lane, turning and facing make sense. But if he’s closer, can he finish over either shoulder.”

By DeGray’s junior season, a young core matured, reaching the state quarterfinals. DeGray, who averaged 21 points, 6.0 rebounds and 2.1 assists, had another source of frustration — a relatively quiet recruitment.

Perhaps he could chalk it up to geography. “Being from Colorado, we’re not really known for basketball,” DeGray said, “so the competition is not as good.”

A stellar summer on the grassroots circuit with Billups Elite, an extension of the training academy established former NBA All-Star Chauncey Billups, might have eased those concerns. Reviewing DeGray’s analytic profile from those 15 games amounts to a potentially compelling argument. Given his playing time and usage, his performance was comparable to future top-150 prospects Isaac Okoro, Chris Ledlum and Juwan Gary.

Yet the July period passed, and DeGray’s list of pursuers still consisted of low- and mid-major programs: Denver, Montana, South Dakota, UTSA and Cal Poly. The Chaparral coaching staff took the Wolverines to team camps for Colorado and Colorado State, giving the Buffs and Rams another chance to see their star up close. Still, both held off extending offers.

Perplexed, Truesdale started placing calls. “What is he missing?” he’d ask. “What can we do? How can we help him be successful and be recruited at the level he wants to be?”

While Truesdale understood some concerns over DeGray’s size, he was confounded when coaches told him they weren’t sure what positional box the player checked. “Call him whatever you want,” he said. “Start him out as a three, and if he continues to grow and develop, he might end up a four.”

Power-conference assistant coaches who put out feelers to DeGray also suggested a possible remedy: prep school. Several mentioned Woodstock Academy, a 200-year-old institution in Norwich, Connecticut, which had recently created a prep program. Assuming DeGray’s game translated against deeper talent in the northeast, programs might be persuaded to move him up recruiting boards.

So, DeGray approached his father with the idea, an audience of one who keenly understood his son’s plight. Two decades earlier, Ronnie DeGray, Jr. needed two years of JUCO after being a lightly pursued forward from southern Louisiana. That detour helped him land at Colorado, where he played alongside Billups in the ‘90s and led to a six-year professional career in Europe.

Rumors of DeGray transferring drifted back toward Truesdale, mostly from his fellow coaches. Confirmation, though, came two weeks in DeGray’s senior year, one where he would have been a frontrunner for Mr. Basketball and contend for the school’s second state title. The night before he met with Truesdale, he broke the news to teammates.

“I knew what I was giving up when I decided to go to Woodstock,” DeGray said. “I’m used to making decisions that are the best for me, and even if I didn’t quite see the results right away, it winds up working out that way.”

When Jacque Rivera sketched out a developmental plan for DeGray, he recalled his first impression as a rival coach. Before arriving at Woodstock, Rivera scouted the combo forward in two matchups for the MacDuffie School. Sure, he spied the lengthy frame, defensive anticipation, and malleable inside-out game. But what caught Rivera’s attention was a conspicuously absent facet. Supplying it topped his to-do list.

“The first thing we needed to do,” Rivera said, “was instill a different mentality.”

If DeGray decamped east expecting a breakout, his first season disabused him of that notion quickly. The roster assembled by coach Tony Bergeron featured eight players who would sign with Division I programs, and his style can be summed up bluntly: kill what you eat.

He built teams that pressed relentlessly and where turnovers were currency. “On offense, you could do pretty much whatever you want,” DeGray said. “If you get a steal, you can shoot a 3 or get a dunk. It’s your possession because you got the takeaway.”

Looking back, DeGray’s clear-eyed about how he adjusted. “That first year was so chaotic,” he said. After the Centaurs rattled off a 38-2 record, Bergeron jumped on an offer to coach college basketball after McCall asked him to join his staff at UMass. But it was sobering for DeGray, who averaged just 5.9 points, 3.5 rebounds and 1.4 assists.

The offers he sought didn’t flood in. The critique offered up by DeGray starts with himself. “I was chasing high-majors and not the best fit for me,” he said. “I had a hard time deciding where I wanted to go. Plus, I didn’t think my mind was ready for college basketball. I wasn’t mentally ready. I wasn’t consistent enough.”

So, DeGray reclassified into the 2020 class and taking a full-blown prep season. Meanwhile, Woodstock hired Rivera, who had played for Bergeron at Wings Academy in New York City. While the pair shared similar principles to mentoring players, they weren’t schematic carbon copies. Rivera’s teams pressed less, and he imposed more structure on the offensive end — albeit with the keen awareness he only had seven months to work with a roster.

“I could spend that time teaching a strict offense,” Rivera said. “But I think they would spend that time frustrated. I would be frustrated. But if I keep it simple and give them confidence — regardless of what we’re playing — they’re going to have a better chance at success.”

Talk with Rivera long enough, and almost every strand of conversation traces back to coaching mentality. The approach is logical looking at DeGray’s first season, but it makes even more sense when you consider his personality: thoughtful, considerate, and soft-spoken. Even at Chaparral, Truesdale thought there were moments where DeGray proved too deferential. After timeouts, he’d pull DeGray aside to issue quiet directives to take over.

“He’s not one to be banging his chest and screaming at guys,” Truesdale said. “That’s never been how he’s wired.”

Instilling the mentality Rivera wanted could also be viewed as permitting DeGray to be more selfish. “Sometimes, you have a gifted player, and they don’t have the best intentions for the group,” Rivera said. “Ronnie always has the best intentions for the group.”

DeGray quickly absorbed Rivera’s counsel. “It’s a dog-versus-dog mentality,” he said. “In Colorado, I wasn’t allowed to coast, but in my mind, I knew I was the best player. At Woodstock, I had to come in and compete. And it was every day, or someone was taking my spot.”

Rivera also wanted to diversify the spots where DeGray got his touches on the floor, making the top of the arc a more frequent catch point. The staff also solicited DeGray’s input on where he felt most comfortable going to work. Again, he mentioned the elbow and mid-post as his preferred locale. They also wanted him to “fly around” as a screener.

Optimizing DeGray in the middle of the floor was just one way Woodstock deployed him. Against a press, the Centaurs cleared out the backcourt and used him as a bigger ball-handler. And when they shrank their lineup, he easily slid down to operate as a small-ball five. “He’s still able to compete on the glass,” Rivera added. “If you look at his arms, he can practically scratch his knees standing straight up.”

Collectively, the results speak for themselves. DeGray’s statistical output more than doubled, finishing at 16.8 points, 7.6 rebounds and 3.0 assists per game, as the Centaurs finished the season at 29-8. An overhaul wasn’t required, just a series of refinements to a game mostly sculpted before DeGray showed up in Norwich.

To understand DeGray’s sharp hardwood intellect, watch him go to work as a cutter: flashing middle and kicking the ball out, sealing for a dump off in the short corner, or reading a defender’s body position before a backdoor cut. “Those skills have served him well,” Rivera said. “However, throughout your high school career and grassroots, it’s not always what people value — even if they swear they do.”

Once DeGray reclassified, he hit the road with Billups Elite for another tour on Adidas’ circuit, this time with a roster stocked with more traditional post players. Despite boosting his efficiency on similar usage, his overall sample size on the wing — just six games — shrunk from the summer before. Exiting the July period, though, one school stepped forward: Mizzou.

When the Tigers offered DeGray in August 2019, it came almost 21 months after he first set foot in Columbia for his unofficial visit. Not without conditions, though. MU was slated to have just one scholarship at its disposal, and DeGray said he was told the staff’s priority was lining up a big man. Seven weeks later, Jordan Wilmore committed.

“It hurt a little bit,” DeGray said. “I was just confused as to why.”

In a typical year, DeGray’s wares might have been attractive during the spring period. However, the early days of the COVID-19 pandemic ushered in a recruiting dead period slated to end June 1, a span of almost 15 months. Ultimately, his connection with Bergeron brought him to UMass, where he became one of seven Woodstock alums on the roster.

A year later, DeGray found himself a target of four power-conference programs in MU, Arkansas, Vanderbilt and Xavier. For Rivera, who watched the initial process play out in frustration, the fact DeGray become a coveted commodity only after entering the portal laid bare a fundamental contradiction.

“He played 40 prep school games and produced,” Rivera said. “You’re telling me you couldn’t understand his value? Now, all of a sudden, he can play in the SEC? What changed? How is the sample different?”

How should we describe DeGray’s freshman campaign for UMass? Promising but disjointed. That’s probably the apt way to put it.

The Minutemen skewed young, but they also returned two more potential double-digit scorers in the backcourt — redshirt freshman T.J. Weeks and senior Carl Pierre – to ease pressure on Mitchell. Bergeron’s connections also paid off when point guard Noah Fernandes, a Woodstock grad, received a waiver after transferring in from Wichita State. The core was sound enough that UMass was picked to finish eighth, solidly in the middle of the A-10 pack.

But after its first COVID pause deep-sixed most of non-conference play, McCall’s group started 2-3, with all three losses coming by five points or less. In two of them, UMass failed to rally from double-digit deficits. Meanwhile, they squandered three leads in a double-overtime loss to George Mason.

Even when the Minutemen notched a pivotal home victory over Rhode Island, it wasn’t without drama, hemorrhaging a 15-point lead over nine minutes. Only a layup rolling off the rim in overtime spared them further anxiety. But amid the drama of an 80-78 victory, DeGray racked up a career-high 23 points, pulled down six rebounds and handed out three assists.

A game later, a blowout of Fordham, DeGray only notched eight points and 10 boards, but it spoke to much-needed versatility. “He’s so invaluable to our team,” McCall told reporters in late January.

At the start of a possession, DeGray might set a drag screen for Fernandes and then pop. If he received a throwback pass, he could shoot, drive or pass the ball to a wing. Then chase that reversal into a side pick-and-roll, one where he slips to a corner to spot up. Later on, after the pattern produces an empty-side ball-screen, DeGray could sprint to the lane-line extended for a kick out.

Parsing out DeGray’s tracking data reveals most of his touches ended with a spot-up jumper, cutting toward the rim, putting back misses, or sprinting the wings in transition. Those touches proved incredibly efficient, producing 1.36 points per possession, according to Synergy Sports.

But with Fernandes in the fold, the ball was rarely in DeGray’s hands during pick-and-rolls. But even chances to dive hard to rim were scant. “Watching games, you’d see the roll never hit,” DeGray said. “It was mostly drive and pops.”

The program’s second COVID pause, however, stalled his progress. While DeGray never tested positive, contact tracing forced him into a 10-day isolation period. Coming back against Fordham, he was placed on a minutes restriction to ease him back into game shape. And he returned to a team missing Mitchell and Fernandes, each sidelined with injuries.

Filling in for Fernandes as UMass’ lead guard, he scored 11 points in a road win at Rhode Island – the last result before a third and final pause sideswiped the group. Yet, in three games against Tier A and B teams in KenPom’s ratings, he averaged 4.3 points, 3.3 rebounds, and shot just 33% from the floor.

Up-and-down seasons are commonplace for many newcomers, and a season unlike any in recent memory might exacerbate the swings. DeGray played 67 percent of minutes, and it only made sense that his usage (15.2%) would grow as a sophomore. Still, he harbored some left him misgivings about the system in which that would take place.

”It was kind of robotic and stagnant,” he said of the spread pick-and-roll system. “It was really easy to guard at times. At times there wasn’t the best shot taken.”

Modern as McCall’s offense might seem, it remains a pattern-based setup, and opponents used common tactics to throw off its timing. Fernandes’ defender might angle their body to force him one direction, while DeGray’s defender plays drop coverage. They might trap the ball-screen, making it hard for him to kick to the ball as DeGray ran a slice cut to the corner.

“You just keep swinging the ball side-to-side,” DeGray said. “But if the defense is switching or being aggressive with those pick-and-rolls, you might not get much. A defender is there to bump, so the roll doesn’t really work.”

Space crunches were also common, DeGray said. Imagine he gets a pass at the top of the key. Often, a teammate’s defender is already cheating in, while the big overseeing Mitchell is already cheating in. Any time he drove a gap, it closed down quickly.

Off the floor, a series of events added intrigue. First, Mitchell announced plans to transfer. Next, Bergeron, who had expected to stay on, saw his contract voided by athletic director Ryan Bamford. “There were some behind-the-scenes things,” DeGray said. “I’m not going to speak on that.”

If nothing else, DeGray’s shown he’s unafraid to venture a risk. So, on April 24, he entered his name in the transfer portal. “I was comfortable here,” DeGray said. “But to get where I want to be, I need to get out of my comfort zone and really be pushed to find that next gear.”

When Mizzou reached out, the conversation picked back up naturally. DeGray not only knew the staff’s values and personality, but there was some familiarity with the city he might call home. In Zoom calls, Martin and the staff said DeGray could return to a hybrid role. “Just be a ballplayer,” he said. “It’s still basketball. You put people in the right positions, good things happen.”

Even if it takes a little bit longer – and a few more detours – than you might have anticipated. “When they came around again, I thought it was funny,” DeGray said. “I was like, ‘Man, we could have done all this a couple of years ago.’”