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.

This stock rising sophomore is one of the top long-distance shooters in the region. Last month Marshall drained 6 triples (22 pts. total) against Germantown Friends as well as 5 threes (15 pts. overall) against Friends Select. His deep range, quick release and constant off ball movement make Bailey difficult to guard. Bailey’s ability to splash transition threes is impressive too. Westtown’s lineup is loaded with DI guards who can get into the paint and collapse the opposing defense. When that happens against Malvern, Bailey should get numerous open looks from deep. If he can knock down those 3-balls, ‘Town stands a good chance of pulling the upset in this 8 vs. 9 game.   

After the latest edition of our 2027 rankings were published, we highlighted Bailey as one of the biggest stock risers in that class. He is an athletic and versatile guard with deep range and a quick trigger on his accurate three-point stroke. Those assets were on full display over the weekend as Bailey knocked down 4 threes on his way to 20 points in ‘Town’s win over Rocktop Academy. It was the second game recently in which Bailey has drained 4 threes.

45 to 13…Bailey is an athletic and fast guard who has quickly carved out a role for himself on this year’s Westtown squad as a 3-point sniper. He is comfortable drilling spot treys, triples coming off screen action and transition threes. Bailey’s logo distance range, quick release and constant off ball movement make him difficult to defend. Bailey’s impressive physical assets and smooth finishing skills enable him to excel on the fast break too. Recently Bailey splashed 4 threes on his way to 23 points against Covenant College Prep.  

With a pure release and an unshakeable coolness, Bailey IV can make shots from anywhere. Hailing from Maryland’s Eastern Shore, the power that extends from his lower body on jumpers is also visible when he high-points the ball on rebounds. His ability to shoot without hesitation and to do the little things make him hard to keep off the floor.