-Bailey enters the DMV after 3 years with Westtown in PA competing against a national schedule, it will be more of the same for a PGCA team that has really reloaded this offseason. Bailey is strong for his size and really excels at creating for himself in the halfcourt. His ability to stretch the floor with his shooting, attack closeouts, and get to the rim should make him a valuable piece for the Flyers this season.

Formerly a do-it-all standout at Easton High on Maryland’s Eastern Shore, Bailey spent the past two seasons at Westtown (PA) refining his perimeter game. The 6-foot-1 guard has emerged as one of the region’s premier perimeter sharpshooters, combining a rapid-fire release with deep range off the catch or off the dribble.

His shooting display at Westtown was capped by a school-record 12 3-pointers in a 38-point explosion against Compass Academy (NJ). He finished the season with 101 made threes while averaging 16.5 points per game.

Now back in Maryland for his final high school campaign at Prince George’s Christian Academy, Bailey’s floor-spacing should immediately create driving lanes and interior opportunities for frontcourt newcomers Nas Abraham Nas Abraham 6'9" | PF/C Prince George's Christian Academy | 2029 State MD and Jayden Mills Jayden Mills 6'7" | PF Bishop Ireton | 2027 VA .

Coming off a standout summer with We R1 that culminated in a 17U Under Armour Association championship, Bailey earned his first Division I offer from Tennessee Tech in June, and that list is destined to expand rapidly as his senior year unfolds.

Bailey is a deadeye shooter from beyond the arc, and once he gets into a rhythm, there are very few ways to slow him down. If he catches the ball with his feet set, the shot is usually finding the bottom of the net. What also stands out is his versatility at the guard position, as he is equally comfortable playing on or off the basketball. Bailey attacked with purpose, seeking out contact and earning frequent trips to the foul line, adding another dimension to his offensive arsenal. His combination of perimeter shooting, positional versatility, and ability to pressure defenses off the bounce makes him one of the more complete guards in the class. Bailey should be a priority target for both low and mid-major programs.

Bailey made it clear that he wasn’t shying away from the trigger right from the jump in their game against Calvert Hall. The 6-foot-1 guard teed off early and often from well beyond the arc and it made no difference if a hand was in his face or not. After picking up his first Division I offer from Tennessee Tech at the conclusion of DMV Live S1, he has the attention of several other programs thanks to his shotmaking, ability to defend either guard spot with impact and his production off little to no dribbles. The sturdy combo guard finished with 19PTS on 5-9 shooting from three in Westtown’s win over Calvert Hall.

Liked the way Bailey found ways to stay relevant in the game. He connected on a pair of three pointers and if he left open from three he will make you pay. Like how he was constantly talking on the defensive end and is an extension of the coach when he is on the floor. Bailey found his way in passing lanes to get steals. Should see division ones tracking him throughout the UAA sessions.

Bailey’s PA Hoops team left with a narrow loss to a talented Difference Makers Elite group but the junior guard opened plenty of eyes with his dynamic scoring performance. The prolific sharpshooter, originally from Maryland’s eastern shore region, nearly shot his team into the second round before anybody realized what had happened, knocking down five quick first half 3’s while demonstrating his pristine mechanics and lightning-quick trigger. Where he really impressed was with the added wrinkles he showed punishing aggressive defenders with smooth and explosive combos off the dribble, knifing into the lane for strong finishes off two feet. Bailey is on a D1 track no matter what but could see some offers come his way sooner than later if he continues showing that type of growth off the bounce.

Bailey nearly did his part to shoot PA Hoops into the second round by himself in the first half alone, knocking down all five of his 3s and scoring the majority of his 27 points in the opening half. One of the most prolific shooters in the state, Bailey showed he needed only a sliver of space to get his shot off with picture-perfect mechanics and polished footwork to get balanced out of a variety of actions. Once defenders started keying on his shot, he was able to break things down with some impressive dribble combos before flashing his dexterity and functional athleticism as a finisher at the rim. He still needs to improve on being able to create his own shot or make plays for his teammates but a D1 program is sure to find value in Bailey’s no-nonsense approach and dynamic shooting ability.

While his teammates were effective getting into the teeth of the defense, Bailey played the part of a quintessential zone-buster from his off-ball role. One of the elite shooters in the region, he was a dynamic spotup weapon against the ANC zone, knocking down 5 3s for his 15 points. While he didn’t do a ton off the bounce, Bailey made quick decisions to get off the ball and maintain the offensive advantage if his shot wasn’t there, and was active on both ends to come up with a healthy dose of loose balls. Bailey’s plug-and-play ability as an elite off-ball sniper who consistently guards his yard on the other end should have him on the radar of high-academic D1 programs across the region.

With shooting being largely the most valuable skill in modern basketball, Bailey figures to be a hot commodity before much longer given his ability to convert in bunches at a high clip from beyond the arc. The eastern Maryland product established himself early on in Sunday’s championship affair and never looked back on his way to 17 points on 5 3s and another jumper with a toe on the line. He displays textbook mechanics with a high-level shooter’s mindset, leaving most in the gym surprised whenever a clean look doesn’t drop through the bottom of the net. Bailey uses his strength, competitiveness, and budding athleticism to make an impact in the floor game as well. While a bit undersized for a primarily off-ball guard, Bailey’s shooting prowess, tough-nosed approach, and pristine academic profile should lead to D1 recruitment before much longer.

With Westtown graduating four seniors to the D1 ranks, it will look to its current crop of sophomores to take big steps up next year, and Bailey figures to lead the charge if the Moose are to stay at the level they’ve become accustomed to over the past decade-plus. A repeat sophomore via Easton (MD), Bailey can be unsuspecting at first glance, but already made a key impact this year with his floor-spacing ability, on-ball defense, and knack for popping up around the ball at key moments. Coming off the bench, he showed a mature ability to impact games efficiently and within the flow of the game. A natural scorer, his growth as a lead guard will be key to monitor in the years to come, but his plug-and-play skillset will surely be valued by D1 coaches when the time comes as he steps into a marquee role for Westtown.