Fleming emerged last season as a valuable secondary scorer at George School and will look to elevate even further in his new surroundings at Penn Charter. While he shined last season primarily as an off-ball floor-spacer and perimeter shooter, Fleming will split lead guard duties for the Quakers while showing off an improved ability to create for himself and others off the dribble. He thrived in the June live periods using his skilled handle and polished footwork to get to his spots in the paint and convert efficiently. The ability to function at either guard spot should continue to see Fleming draw D1 attention with a number of D2 programs hoping to see him continue to fly under the radar.

Penn Charter’s roster is full of talented underclassmen, which makes Fleming’s presence that much more important as a senior. Still, he’s new to the group after making his way from George School, but it hasn’t taken long for the 6-foot-3 lead guard to provide the needed stability, execution, and leadership for head coach Brandon Williams. The Quakers had two tough opponents in Mt. Carmel and Clinton Grace. While both games resulted in close losses, Fleming’s production was felt in a multitude of ways.

As a scorer he showed patience operating in ball screens where he’d force a switch and tactfully take advantage of a slower-footed big guarding him. His change-of-pace attack allowed him to create space and when he rises up from mid-range or beyond the arc, Fleming maintains good balance. He’s unselfish and uses the attention he demands on the catch to make the extra pass or dribble drives to collapse the defense and then find others for clean looks.

Fleming provided a nice pop of scoring for his NJ Beasts squad. He showed that he can find the rim in different ways. Fleming had a nice mid-range shot where he put the ball on the deck to get to the spot he wanted to convert from. His calling card is his marksmanship from behind the three point line, if his feet are set there is a high chance his scoring from deep. On defense Fleming found ways to alter shots and get steals. He is getting recruited by scholarship programs.

After his stellar performances at the Mid-Atlantic Independent School’s Team Camp, it should not be a surprise that Fleming’s recruiting is heating up. At MA-ISTC Fleming scored at every level as he posted a 30-piece as well as a 27-point game.Recently Flemingreceived offers from Rider and Navy.

Based on his stellar performances at the Mid-Atlantic Independent School’s Team Camp, Fleming’s move to Penn Charter appears to be a perfect fit for his skill set. This past weekend, Fleming scored at every level as he posted a 30-piece as well as a 27-point game. Fleming popped triples of every variety. He was especially effective shooting threes after throwing a jab step or executing a quick crossover. Fleming also continued to prove that his ball handling skills have taken a significant step forward. His ability to attack the paint off the dribble and get to the rim for a lay-in was remarkable. He also blew past initial defenders, threw on the breaks in the mid-range and then hit pull up jumpers. His step-back / fadeaway jumper was impossible to stop. On several half-court possessions, Fleming even operated as a primary ball handler.  

This former George School standout (17 ppg. & 5 rpg.; 57 made threes in 2024-25) looked right at home with his new Penn Charter teammates. Of course, Fleming drilled threes from all-around the arc. A few of those triples were from NBA range and several impressive made threes came off the bounce. Still, it was Fleming’s point guard skills that really grabbed our attention at the Rare Footage Pre-Live event. Fleming frequently worked as the primary ball handler and initiated PC’s offense with poise. His change of direction handles, and court vision enabled him to rip opponents off the dribble for lay-ins and dimes to teammates. As a bonus to his half-court point guard skills, Fleming pushed the rock in transition for scores and assists. At the other end of the court, Fleming was a high IQ, plus defender.

Named MVP for the White Team. This is the second weekend in a row I’ve been impressed with Kasey and how he operates. A solid two-way guard that shows a tremendous feel, is crafty, sneaky quick and crafty, and a true playmaker on the court. He continues to show his ability to get others the ball, using his pace and creativity to set up others but also uses the same quickness to get by defenders and score. Truly love his overall feel for the game, especially leading the charge.

This athletic prospect with a highly accurate jump shot averaged 17 points and 5 rebounds per game during his junior season. Fleming knocked home 57 made threes and was effective in the transition game too. This past week Fleming took an official visit to Penn.

Joining Miller in taking advantage of the opportunity presented by the transfer of Sutton and season-long injury of senior big Luke Bevilacqua Luke Bevilacqua 6'10" | C George School | 2025 State #68 Nation PA (Lafayette), Fleming seized the open scoring role in the George lineup while vaulting himself from a small-college prospect to one who looks bound for the scholarship level. Previously more of a jack-of-all-trades utility guard, Fleming established an identity this winter as a dynamic shotmaker, with the confidence and versatile mechanics to translate that role up in levels. From that role, he’s able to take advantage of closeouts to attack off the dribble for swift finishes or high-IQ passing reads. He doesn’t jump off the page physically and his game may not be the sexiest, but Fleming’s production, efficiency, and contributions to winning figure to become impossible to ignore before much longer.

The game’s leading scorer, Fleming did his part to keep George in the game while his backcourt mate battled foul trouble. He knocked in four 3’s en route to his 22 points, showing pristine mechanics firing off the catch in the halfcourt or transition. When run off the line, Fleming was able to knife into the defense for multiple smooth finishes. The toughness and IQ he brings to the floor have come to be expected of him. Fleming could be a gem for the high-academic D3 level but has risen himself firmly into scholarship conversations with his play this season.