Winters Grady Scouting Deepdive
After proving to be an effective primary and secondary scoring option at the high school level, the versatile four-star prospect must now integrate into a potentially elite Michigan roster.
At times, we place such an intense focus on the top prospects in high school basketball that we fail to properly evaluate the ancillary players surrounding them. Many of basketball’s top prospects play on national contending teams, meaning they likely aren’t the only elite player on their roster. These elite “role players” tend to be vastly underrated relative to their peers, which regularly leaves evaluators shocked when they break out for their college program. This could be the case for today’s subject, Winters Grady, who plays second-fiddle to the best player in the 2025 graduating class, Darryn Peterson, but who consistently shines both in a primary and secondary role. The consensus top 100 recruit heading to Michigan could have been ranked far higher had he decided to attend a less prestigious school, but instead he chose to be the second option at Prolific Prep, one of the best prep schools in the nation.
Player Profile:
Winters Grady is a 6’6” and 190lb shooting guard from Lake Oswego, Oregon who began his prep career at Lake Oswego High School before transferring to Prolific Prep. He played AAU basketball for Jalen Green Elite on the Adidas 3SSB circuit. Before committing to the Michigan Wolverines and head coach Dusty May, he collected offers from prestigious programs such as Oregon, Iowa, Creighton, Oklahoma, Washington, USC, Xavier and many more.
He was the primary scoring option for Jalen Green Elite (17U) last summer and averaged 19 points per game on shooting splits of 53% from the field, 42% from beyond the arc, and 87% from the free-throw line. It was during this AAU season where he proved he could operate as an efficient first option on the offensive end, which led him to garner more attention from college programs. During the 2024-25 season with Prolific Prep on the Grind Session circuit, he posted averages of 13.1 points, 4.4 rebounds, 1.7 assists, 1.2 steals, and .1 blocks per game. Throughout his time with Prolific Prep, he proved to be one of the better second options in all of high school basketball alongside top-ranked recruit Darryn Peterson. In games where Peterson was unable to/didn’t play, Grady was able to seamlessly step into the first-option role, where he ensured that Prolific Prep remain undefeated in the Grind Session. This role versatility could prove to be incredibly valuable for him once he reaches higher levels of the sport.
Interior Scoring:
The issue most evaluators face when considering Grady as a potential college star and NBA prospect is falling into the trap of believing he’s only a shooter. Sure, most of his points come from the mid-range and beyond the arc, but he’s also a very real around-the-rim scorer. He’s not a spectacular vertical athlete and he doesn’t possess elite burst, but he has a shockingly tight handle for an off-ball two-guard and is an absolute contortionist under and around the rim. He has elite touch from everywhere on the court, but it’s his soft touch on at-the-rim attempts which rounds out his offensive arsenal beyond pure marksmanship.
He’s proficient at attacking the rim from the perimeter with the ball in his hands, and he possesses several key traits that support his success in this area. As previously mentioned, he has an advanced handle which allows him to create the advantages necessary to open driving lanes. He’s also surprisingly strong, capable of creating space on his way to the basket and once he’s gotten there by lowering his body into his defender or throwing a shoulder into an opponent's chest. He’s excellent at finishing through contact but isn’t fantastic at finishing over vertical contents from lanky interior defenders. Finally, his mid-air body control is absolutely elite, and he has a deep bag of tricks under and around the rim to create advantageous finishing angles. All in all, I trust his on-ball driving and finishing to translate to all levels of the sport, with his only major flaws being his lack of vertical pop and ability to foil vertical contests from rim protectors.
A lot of top-tier shooting guard prospects are significantly better attacking the rim away from the ball than they are on it. I don’t believe this to be the case for Grady, but I do think he could play the role of off-ball cutter if that were asked of him within a system. His lack of elite first-step acceleration and above-the-rim finishing abilities limit his upside as an off-ball slasher. That said, he’s a smart player and an offensive opportunist who has proven to be excellent at choosing when to leave his post along the perimeter and cut to the basket. He’s simply much better at creating advantages with his handle and outside scoring gravity than he is with his athleticism, but I don’t think that completely handicaps his ceiling in this area. He’s a versatile interior scoring option and will give coaching staffs a ton of flexibility when deciding how to utilize him.
An area where I see potential for significant growth from Grady is attacking the rim in transition and on the fast break. I didn’t see a ton of opportunities for him in this area throughout my dive into his film, but it would make sense for him to thrive in these situations. Why? Because he’s able to substitute his poor first-step burst for pure speed and on-ball self-creation. He isn’t a slow player; it simply takes him longer to reach his top speed. Like I said, he’s also better at creating advantages with the ball in his hands than without. Finally, he’s a very good defensive rebounder for a two-guard, which means he should be pushing the pace more than he did this year. This was probably the case because he was immediately releasing to Peterson or throwing full court passes to streaking teammates instead of taking it up himself. I don’t expect him to play this role during his first year at Michigan considering he’ll be sharing the floor with Elliot Cadeau, an elite passer and pure point guard, but it’s worth noting he could handle this responsibility in the future.
Mid-Range Scoring:
For those of you who still appreciate a throwback mid-range heavy game, you’re going to love Winters Grady. In most cases I’m weary of players who rely as heavily on this scoring level as he does, but he managed to adopt this playstyle while maintaining excellent efficiency throughout his prep career. This is where his shot looks the most fluid, and where he’s clearly the most comfortable and confident. Unlike most prospects, I’m fine with him falling back on this scoring level as long as his shooting splits remain strong. Considering he will likely be scaling his role down at Michigan next season, I expect him to be even more efficient than he has been over the past year. My only worry is that he won’t be allowed to operate from this level how he has in the past, which I do believe would limit his output and ceiling.
I’d argue the two most important shots from the mid-range/in-between level are the pullup jumper and the floater/push shot. These shots best bridge the gap between the close-range and long-range scoring levels. Grady is incredibly proficient at both. The pullup jumper is the strongest shot in his mid-range arsenal (maybe his entire offensive arsenal), and not only can he create these looks in a myriad of ways, but he’s also able to knock them down no matter how well they’re defended. As I’ve mentioned, his burst isn’t elite, but his ability to decelerate and stop on a dime is high level. That skill directly supports his ability to get his mid-range pullup jumper off at all times. He also creates space using his handle and the occasional (perhaps illegal) push-off. However, he doesn’t need a ton of space to convert on these attempts. He has fantastic lift and a high release point on these looks and is rarely deterred by even the best contests.
When he finds himself already within the perimeter, whether that be because he receives a pass there or because he has backed his opponent down (which he likes to do), he’s able to create the necessary space to get his shot off cleanly. As I said, strong contests do not seem to bother him from this range, and neither does significant contact. While he (obviously) doesn’t always make the shots in these situations, he draws a ton of fouls on aggressive defenders who are doing everything in their power to keep him from getting a clean look from this range.
Like I said, Grady has a strong floater game which further diversifies not only his in-between scoring but also his overall offensive arsenal. His touch on these looks is strong, and this part of his game will almost certainly translate to every level of the sport. That said, it is worth noting that he only attempts these shots from the front and right side of the basket. He makes a legitimate effort to get to his strong side on these attempts, which does make him significantly more predictable. I don’t think this is that big of a deal, but him developing an all-around floater game would drastically improve his offensive versatility and unpredictability.
Outside Shooting:
Despite Grady’s strong mid-range scoring acumen, most assume that his role for Michigan next season will be off ball outside shooter. While I obviously believe that he could be far more than this, I don’t disagree that this role would suit him for his debut campaign. Luckily for him and for Michigan, he’s an excellent outside shooter, both with and without the ball. Unlike his mid-range game, he’s more proficient away from the ball than he is with it from this range, which suggests he will seamlessly fit into this ancillary role next year. I highly doubt he starts for the Wolverines next season, but I am of the opinion that his outside shooting skills would fit perfectly alongside the passing and playmaking skills of starting point guard Elliot Cadeau. Whether he starts or not, he’ll offer the Wolverines a ton of lineup and rotation flexibility.
His catch-and-shoot long range marksmanship is simple and effective. He possesses a fluid and consistent shot motion and a high release point. His mechanics here are not quite as smooth as his mid-range mechanics, but apart from slight differences I don’t think this is a big deal. Even if his mechanics from this range were far worse, all that really matters is that these shots go in at an efficient clip. What makes Grady such an intriguing off ball outside shooter is his ability to maintain his strong mechanics while moving and while off-balance. He’s incredibly dangerous as a relief option on the fast break, coasting into the corner or trailing the ball handler for on-the-move catch-and-shoot triples. All in all, his ability to remain effective and efficient from beyond the arc in basically any scenario ensures that he’ll find some level of success at the college level.
His on-ball outside shooting is similar to his pull-up mid-range shooting in that he’s able to quickly square up his body and go up for his shot in one fluid motion. As I’ve already mentioned, he’s clearly not as fluid from long range as he is from the mid-range, but he still appears far more comfortable in this area than most of his peers. His strong handle goes a long way from a space creation perspective considering his movement with the ball isn’t the best. While I still believe that his off-ball shooting is far more feasible in the present, I do think to reach his ceiling he will have to adopt more on-ball shooting responsibilities. That said, I’m not sure his ceiling (if what I’m saying about his on-ball shooting is true) will be more conducive to success than playing an off-ball role next to an elite on-ball guard.
Passing & Playmaking:
Passing is an area where I could see Grady making massive strides throughout his career. We weren’t able to see a ton from him in this department throughout his prep career considering the role he most often found himself playing, but the flashes he showed were more than intriguing. I highly doubt he’ll ever be a primary initiator or floor general, nor do I believe that this is a role he should strive to play, but his secondary-playmaker potential seems very real. He’s a heads-up passer who operates at all three levels, allowing him to set his teammates up in a myriad of different advantageous positions.
Grady’s most important trait as a passer is his immense scoring gravity. His ability to collapse a defense by simply possessing the ball is something that will naturally allow him to be, at least, a solid passer. He’s already proven that he’s willing and able to find teammates around the rim whenever given the opportunity. He’s also very proficient at pushing the pace in transition with full court passes to streaking teammates. He’s at his best when he penetrates the interior, where defenders are forced to step to him out of respect for his mid-range scoring capabilities. When this happens, he’s able to deliver dump off passes to big men positioned at the dunker spot or to slashing wings who cut along the baseline. Assuming he remains a major threat from the mid-range, this should remain a primary element of his passing game.
Where he does struggle is creating opportunities for teammates along the perimeter. He’s okay acting as a connective passer, swinging the ball around the arc to open shooters. However, he rarely creates/initiates an open look with his passing. He’s not great at kicking it out on his drives, in fact, I didn’t find a single instance of him doing this for a made three throughout my film dive. That said, a lot of his drives do end in the mid-range. I think his connective passing will be useful throughout his career, but don’t expect him to utilize his defensive manipulation to find teammates beyond the arc at a significant rate.
Defense:
I wouldn’t consider Grady to be worth writing home about on the defensive end, but he’s probably better on this end of the floor than most people would give him credit for. He has good size and a solid frame, and as we’ve covered a few times already, is surprisingly strong considering his lack of many other standout physical traits. His lateral movement is better than his north-south movement, allowing him to stick with most opposing shooting guards along the perimeter. He’s a tad out of his element when switched onto quicker point-guards or frontcourt players, but I feel confident projecting him to hold his own against most shooting guards and wings.
When you watch him play, it’s evident that he’s far better defending away from the ball than he is defending a ball handler. He’s a defensive opportunist willing to jump passing lanes, and it’s clear that he has a strong understanding of how to impact the game defensively despite his physical limitations. His timing on switches is almost always perfect and he properly picks and chooses when to take risks. For example, when an opposing big attempts to post him up inside, he will throw himself in front of an entry pass and risk allowing easy interior offense because he knows he can’t defend the post up. He’s far more conservative when defending an opponent he knows he can stick with. This high IQ defense allows me to feel comfortable that he won’t be a serious defensive liability anytime soon.
He doesn’t pick up many blocks, but I wanted to include the few blocks that I did find to illustrate the effort he gives on this end of the floor. I’m of the opinion that if he doesn’t give a ton of effort on the defensive end, he could become a legitimate liability in the future. Luckily, he’s a high intensity player who doesn’t give up on defense, even when he’s already been beaten. His recovery efforts don’t always result in defensive stops, but I’m happy to see that he’s usually willing to attempt a recovery effort. As long as he maintains a strong defensive motor, along with his strong feel for every aspect of the game, he should be able to make an impact as a defender.
Summary:
Before summarizing Grady’s game, I want to list out any and all of his weaknesses and flaws so that we can get a better feel for his game in its entirety. I include this disclaimer in all my scouting deepdives, but it’s important to remember that every player has countless flaws. What makes the best players in the world the best at what they do is that they look at these weaknesses as areas in need of improvement, not as areas devoid of potential for improvement.
As I’ve mentioned several times throughout this write up, Grady lacks strong first-step acceleration and burst from the perimeter. If this remains the case, his ceiling as both an on-ball and off-ball interior scorer will be limited.
He’s not a great vertical athlete, and while he does finish through contact well, he struggles to finish against physical rim protectors considering he can’t finish over them.
While he is a constant off-ball mover, he’s not the most dynamic away from the ball considering his physical limitations. Even when he does beat an opponent off the ball, skilled defenders are usually still able to recover to him.
He relies heavily on his mid-range and in-between games, the scoring level most consider the least efficient of the three major scoring levels. While he has remained efficient from this range throughout his prep career, this is going to become more difficult as he progresses through higher levels of the sport.
For someone who does rely on his floater to make up for some of his interior shortcomings, he seems unable to convert on floaters from the left side of the basket. To continue diversifying his game, he will need to develop a more well-rounded floater.
His outside shooting is relatively one-dimensional. While he is capable of creating his own shot from beyond the arc, he’s so much better as a catch-and-shoot operative that there really is no point in him working on the ball from long range.
When he’s not sharing the floor with an elite lead guard (Darryn Peterson this season), he can seriously suffer from an efficiency perspective. Once he’s forced to shoulder more offensive weight, he will occasionally suffer from shot chucking issues.
For someone who finds himself with the ball in his hands at all three levels, he struggles to find open teammates beyond the arc. This is strange considering he’s a solid passer to cutting teammates and big men near the basket.
Most of his defensive issues stem from the physical limitations we’ve already covered. He’s not a fantastic athlete vertically or horizontally, yet he still manages to make an impact defensively. The issue is that defense is going to get more and more difficult at higher levels of the sport.
To summarize Winters Grady’s game, I’d make the argument that he combines the skillset of a shooting guard with the IQ of a point guard. If he were quicker and a more willing passer, there’s a world where he’d make a solid floor general. However, he does lack a few traits that are typically necessary for lead guards, while possessing other traits that make him the perfect secondary scoring option. He’s an elite shooter from beyond the arc and from the mid-range, and supplements this shooting acumen with solid interior scoring and on-ball self-creation. While he may not be a team’s first option on the offensive end, he is skilled enough to take over on the ball when he’s feeling good. If it weren’t for his athletic limitations, he would be about as well-rounded on the offensive end as any high school player in the nation.
Next year at Michigan he will almost certainly come off the bench, but I think the coaching staff would be foolish to leave him out of the rotation altogether. He is simply too effective at some of the most important elements of the sport for me to believe that he won’t contribute to winning basketball, especially at the college level. As he progresses through his career, I expect his role to be scaled down, with him serving as an elite catch-and-shoot off-ball two-guard if he ever makes the NBA leap. He has the size and skills necessary to succeed in the best league in the world, and if he continues to polish his game, I don’t think his athletic limitations will hold him back as much as I may have led on through this piece. Grady proved to be a winner at the high school level, will now join the ranks of a program on the rise, and could potentially make a difference as an impact role player in the NBA. I’d argue that’s the blueprint for an enticing prospect for any team looking to win on the margins.