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Top 2027 757 Guys to Watch

Top 2027 757 Guys to Watch
Riley Highfill
Riley Highfill March 2, 2026 @ 04:22 PM
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In this article:

Trent Smalling
Trent Smalling 6'3" | SG | 2027
VA
Nathan Lessley
Nathan Lessley 6'6" | PF | 2027
VA
Dean Williams
Dean Williams 6'4" | SG | 2027
VA
<!-- wp:paragraph --> <p>The 757 continues to produce high-level talent year after year, and the 2027 class is no exception. The region is loaded with guards and wings. They can score, defend, and impact the game in multiple ways. This summer will be a proving ground for many of them.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>With the travel circuit around the corner, college coaches will be making consistent stops in Hampton Roads. These four prospects have already shown they can produce at a high level during the high school season. Now, the focus shifts to how they translate that success onto the AAU stage.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>Here are four 2027 standouts in the 757 who should be firmly on recruiting radars.</p> <!-- /wp:paragraph --> <!-- wp:acf/evaluation-block {"name":"acf/evaluation-block","data":{"player_evaluations_0_player":["3035379"],"_player_evaluations_0_player":"field_62ab9d62ecf2c","player_evaluations_0_override_profile_image":"","_player_evaluations_0_override_profile_image":"override-player-profile-image","player_evaluations_0_not_in_database":"","_player_evaluations_0_not_in_database":"field_62aba48cecf2d","player_evaluations":1,"_player_evaluations":"field_62aba7547dc44"},"mode":"preview","alignText":"left","anchor":"acf-block-69a60db795c4f"} --> <!-- wp:paragraph {"placeholder":"Add evaluation here...","className":"text-gray-700"} --> <p class="text-gray-700">Trenton Smalling brings athleticism and aggression every time he steps on the floor.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>At 6'3”, he's a downhill guard who thrives attacking the rim. He finishes above contact and through defenders, putting constant pressure on opposing defenses. His ability to get into the paint consistently makes him difficult to contain, especially in transition.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>Smalling was a major impact player for Woodside this past season and showed he can carry scoring responsibility. He's also a capable shooter, which keeps defenders honest and opens up driving lanes.</p> <!-- /wp:paragraph --> <!-- wp:paragraph {"placeholder":"Add evaluation here...","className":"text-gray-700"} --> <p class="text-gray-700">This summer, by playing with [program_tooltip program_id='3424568' first='Team' last='Loaded Gold'] 17U, he'll have a big opportunity. He can showcase his all-around scoring ability against strong competition. His blend of athleticism, physicality, and confidence points toward a very solid college trajectory.</p> <!-- /wp:paragraph --> <!-- /wp:acf/evaluation-block --> <!-- wp:acf/evaluation-block {"name":"acf/evaluation-block","data":{"player_evaluations_0_not_in_database":["not_in_db"],"_player_evaluations_0_not_in_database":"field_62aba48cecf2d","player_evaluations_0_player_details_selected_featured_image":"","_player_evaluations_0_player_details_selected_featured_image":"field_62cca28ffa4e7","player_evaluations_0_player_details_player_name":"MJ Montague ","_player_evaluations_0_player_details_player_name":"field_62aba4c9ecf2f","player_evaluations_0_player_details_graduating_class":"2027","_player_evaluations_0_player_details_graduating_class":"field_62aba4ddecf30","player_evaluations_0_player_details_height":"6'3u0022","_player_evaluations_0_player_details_height":"field_62aba4e8ecf31","player_evaluations_0_player_details_position":"77244","_player_evaluations_0_player_details_position":"field_62aba4f0ecf32","player_evaluations_0_player_details_school":"Woodside ","_player_evaluations_0_player_details_school":"field_62aba4fdecf33","player_evaluations_0_player_details_club_program":"[program_tooltip program_id='3424568' first='Team' last='Loaded Gold'] ","_player_evaluations_0_player_details_club_program":"field_62d20e723441a","player_evaluations_0_player_details":"","_player_evaluations_0_player_details":"field_62aba4afecf2e","player_evaluations":1,"_player_evaluations":"field_62aba7547dc44"},"mode":"preview","alignText":"left","anchor":"acf-block-69a60db795d1c"} --> <!-- wp:paragraph {"placeholder":"Add evaluation here...","className":"text-gray-700"} --> <p class="text-gray-700">MJ Montague is a strong, crafty guard who plays with confidence and edge.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>He has an elite shooting stroke. He can light it up from beyond the arc. However, his offensive game doesn't stop there. Montague scores at all three levels, using his strength and footwork to create space. He's comfortable attacking closeouts, pulling up mid-range, or finishing inside.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>What separates MJ is his two-way impact. He's an elite defender who rarely takes possessions off. He competes, pressures the ball, and embraces tough matchups. His ability to guard multiple positions makes him valuable in different lineup combinations.</p> <!-- /wp:paragraph --> <!-- wp:paragraph {"placeholder":"Add evaluation here...","className":"text-gray-700"} --> <p class="text-gray-700">With [program_tooltip program_id='3424568' first='Team' last='Loaded Gold'] this summer, Montague has a real chance to elevate his profile. His versatility, defensive motor, and scoring confidence all project well to the next level. He looks every bit like a future college player.</p> <!-- /wp:paragraph --> <!-- /wp:acf/evaluation-block --> <!-- wp:acf/evaluation-block {"name":"acf/evaluation-block","data":{"player_evaluations_0_player":["2470603"],"_player_evaluations_0_player":"field_62ab9d62ecf2c","player_evaluations_0_override_profile_image":"","_player_evaluations_0_override_profile_image":"override-player-profile-image","player_evaluations_0_not_in_database":"","_player_evaluations_0_not_in_database":"field_62aba48cecf2d","player_evaluations":1,"_player_evaluations":"field_62aba7547dc44"},"mode":"preview","alignText":"left","anchor":"acf-block-69a60db795d73"} --> <!-- wp:paragraph {"placeholder":"Add evaluation here...","className":"text-gray-700"} --> <p class="text-gray-700">[player_tooltip player_id='2470603' first='Nathan' last='Lessley'] checks a lot of boxes that college programs look for in modern wings.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>At 6'6”, he brings length, athleticism, and shooting ability — a combination that translates. Lessley is an elite perimeter shooter who can space the floor immediately, but he's also aggressive when attacking his spots.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>He handles the ball well for his size and plays with noticeable confidence. He is comfortable rising up off the catch. He is also at ease creating space off the bounce to take difficult shots. He makes those tough shots too.</p> <!-- /wp:paragraph --> <!-- wp:paragraph {"placeholder":"Add evaluation here...","className":"text-gray-700"} --> <p class="text-gray-700">His versatility allows him to guard multiple positions and contribute in transition as well. With his physical tools and skill set, Lessley is poised to be on plenty of recruiting boards this summer.</p> <!-- /wp:paragraph --> <!-- /wp:acf/evaluation-block --> <!-- wp:acf/evaluation-block {"name":"acf/evaluation-block","data":{"player_evaluations_0_player":["2470557"],"_player_evaluations_0_player":"field_62ab9d62ecf2c","player_evaluations_0_override_profile_image":"","_player_evaluations_0_override_profile_image":"override-player-profile-image","player_evaluations_0_not_in_database":"","_player_evaluations_0_not_in_database":"field_62aba48cecf2d","player_evaluations":1,"_player_evaluations":"field_62aba7547dc44"},"mode":"preview","alignText":"left","anchor":"acf-block-69a60db795db8"} --> <!-- wp:paragraph {"placeholder":"Add evaluation here...","className":"text-gray-700"} --> <p class="text-gray-700">[player_tooltip player_id='2470557' first='Dean' last='Williams'] has already built one of the stronger scoring resumes in the 757.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>Williams is one of the top guards in the region, regardless of class. He was a major reason Catholic High School had such a successful season. He can score from all three levels and is an elite shot maker, especially from deep.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>Defenses have to account for him at all times. He's comfortable taking big shots and has consistently delivered in pressure moments. Beyond scoring, he competes defensively and brings physicality to the guard position.</p> <!-- /wp:paragraph --> <!-- wp:paragraph {"placeholder":"Add evaluation here...","className":"text-gray-700"} --> <p class="text-gray-700">Williams has the tools and production of a high-level college player. Expect him to be firmly on the radar of college coaches throughout the summer evaluation period.</p> <!-- /wp:paragraph --> <!-- /wp:acf/evaluation-block --> <!-- wp:heading {"level":3} --> <h3 class="wp-block-heading">Final Thoughts</h3> <!-- /wp:heading --> <!-- wp:paragraph --> <p>The 757's 2027 class is loaded with competitive guards and wings who can score and defend at a high level. Smalling brings downhill pressure. Montague shows two-way toughness. Lessley combines size and shooting. Williams offers proven production. All of these attributes make for a strong group heading into the travel season.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>Summer basketball tends to separate prospects. This group has the skill, confidence, and work ethic to make a statement.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>Don't be surprised if their names carry even more weight by the end of July.</p> <!-- /wp:paragraph -->

The 757 continues to produce high-level talent year after year, and the 2027 class is no exception. The region is loaded with guards and wings. They can score, defend, and impact the game in multiple ways. This summer will be a proving ground for many of them.

Trent Smalling

Trent Smalling

VA
SG
HEIGHT 6'3"
POS SG
CLASS 2027
View Player
​
Trent
Smalling SG
Class
2027
Height
6'3"
HS
Woodside
|
VA
Top 2027 757 Guys to Watch
Trenton Smalling brings athleticism and aggression every time he steps on the floor. At 6’3”, he’s a downhill...
Written by Riley Highfill
Read more at PrepHoops.com
Prep Hoops

Trent Smalling

State: Virginia
School: Woodside
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Highlights

MJ Montague

MJ Montague

HEIGHT 6'3"
POS CG
CLASS 2027

MJ Montague

School: Woodside
Club: Team Loaded Gold
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Nathan Lessley

Nathan Lessley

VA
PF
HEIGHT 6'6"
POS PF
CLASS 2027
View Player
​
Nathan
Lessley PF
Class
2027
Height
6'6"
HS
Cox
|
VA
Top 2027 757 Guys to Watch
Nathan Lessley checks a lot of boxes that college programs look for in modern wings. At 6’6”, he...
Written by Riley Highfill
Read more at PrepHoops.com
Prep Hoops

Nathan Lessley

State: Virginia
School: Cox
Subscribe below to view this player's evaluation

Highlights

Dean Williams

Dean Williams

VA
SG
HEIGHT 6'4"
POS SG
CLASS 2027
View Player
​
Dean
Williams SG
Class
2027
Height
6'4"
HS
Catholic
|
VA
Top 2027 757 Guys to Watch
Dean Williams has already built one of the stronger scoring resumes in the 757. Williams is one of...
Written by Riley Highfill
Read more at PrepHoops.com
Prep Hoops

Dean Williams

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State: Virginia
School: Catholic
Club: Team Loaded VA
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Highlights

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