When Oskhosh North head coach Brad Weber called Josh Dilling up to varsity for the playoffs in 2018, he didn’t do so because he wanted the sophomore guard to play — he wanted him to watch.
Granted, Weber knew Dilling was capable of playing if it came to that, but the Spartans’ backcourt was loaded already. At point guard, they had Wisconsin Player of the Year Tyrese Haliburton, currently projected as a lottery pick in this year’s NBA Draft. Alongside him was Quincy Anderson, now playing for Minnesota State.
Dilling remembers one particular practice from that postseason. Oshkosh North’s big man wasn’t his normal self that day. He couldn’t catch the ball or make a layup to save his life. Haliburton noticed, and pulled his teammate aside. For five minutes, with practice going on around them, the two just talked, the future Iowa State star trying to pull his teammate together.
Incidents like that were what Weber wanted Dilling to observe and digest. Dilling knew it.
“(Haliburton) taught me a lot about just being that leader for the other guys,” Dilling said. “ … Obviously, he’s a great talent, so I can’t say it was just the leadership part, but … the coaches pulled me up just to learn from guys like Ty.”
Dilling was only a situational substitute during the Spartans’ postseason run, which culminated in the school’s first state championship. But with Haliburton, Anderson and four other seniors graduating, Dilling knew he’d have to do much more next season.
That he was. He averaged 14.8 points and 4.9 assists per game as a junior, while shooting 45 percent from deep. His senior year, he boosted his scoring average to 19.8, and more time in the weight room helped him not only attack the basket more, but double his rebounding average from 2.7 to 5.4.
“He’s a good shooter and very good at passing, especially in the open court,” Weber said. “ … His ability to finish around the rim and to take that first bump on drives really improved from his junior year to senior year. He was able to control his body and the defender a lot more.”
These numbers and all-around improvements put him on the radar of Minnesota Crookston. Around Christmastime, Dilling learned that assistant coach Bryan Beamish would be attending a holiday tournament where the Spartans were playing. But the Golden Eagles’ interest really picked up after the season.
One morning in March, Dilling got a phone call from the father of Quintin Winterfeldt, a former standout at Waupun H.S. who grew up a year ahead of Dilling in Fond du Lac and still met Dilling often for YMCA pick up games. Winterfeldt was now a Golden Eagle, and his father had an inkling that Dilling was interested in being one too.
That assumption proved correct. Later that day, UMC head coach Dan Weisse — an Oshkosh native himself — called, and the Golden Eagles’ recruitment began in earnest. In April, Dilling committed to Minnesota Crookston.
“He’s been on our radar since junior year,” Weisse said in April. “The Fox Valley Conference, maybe I’m biased, but it’s definitely one of the best conferences in Wisconsin, and he’s played against some high level competition. To be a first-teamer in that league, he’s been-there, done-that.”
Dilling is candid when talking about his game. He has the dribbling and passing skills of a point guard, but at 6-foot-4, can also play out on the wing. He and Weber struggle to come up with a real comparison for him, but Dilling’s best guess is “a very knock-off version of Luka Doncic”: the young Dallas Mavericks star who beats his opponents not with overwhelming physical attributes, but with guile, creativity and technical skill.
“I have no vertical, I’m not slow but I’m not lightning-fast, and there’s no flair, there’s no dunking,” Dilling said. “I can shoot well, I have the dribbling ability, I have those guard skills as I get bigger, but honestly, I would just call my playing style very unorthodox.”
As such, Weisse is intrigued by Dilling’s versatility. He sees him as a natural point guard, but someone who can also play the ‘2’ or even the ‘3’ in the Golden Eagles system. And just as importantly, he thinks Dilling can do so right away.
Privately, Dilling had been frustrated with his role as a sophomore. He was confident he’d make varsity that year, but two transfers arrived instead. He was left watching players his age, that he’d grown up playing against, get big minutes for rival schools while he rode the pine.
But that kind of frustration is merely human. And Dilling knew there was only so much he could do about it.
In a recent conversation, he and his parents looked back on his high school career, and one of the things brought up was regrets. Between a state title, two All-Conference nods, a college scholarship and getting to learn from Haliburton and Anderson, it’s not clear if he has any at all.
“It sucks not getting three, four years on varsity, but you gotta take what you get, you know?” he says. “ … Getting two full years as starting point guard, can’t complain with that. And I got to experience a state championship. That whole experience was incredible.”
As a result, Dilling brings a level-headed perspective to his first year in Crookston. He’d love to play major minutes, but he knows nothing’s guaranteed. On a wide-open roster with 12 newcomers, there’s no expectation other than to compete for a spot. If he earns one, great. If not, he says he’ll do his best to help the Golden Eagles in any way possible and digest all he can from the bench — just as he did in 2018.
“If you can defend and you can find your role, you’re gonna be able to make a splash early on,” Weber said. “And Josh is a very well-rounded player and can understand that. Do we need someone to create and dish? Do we need someone who’s gonna knock down open shots? He’ll figure it out.”
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