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Mason Brooks and James Pennington

Mason Brooks and James Pennington were childhood friends and members of The Ride-or-Dies, the Baltimore friend group centered on Logan Weston.

Overview

Mason and James were the group’s two White members. Mason belonged to the earlier gifted-academy circle, while James joined after moving from England to Baltimore. They became a comedic pair within the larger group: James brought theatrical performance and dramatic movement, while Mason supplied trash talk, deadpan observations, and physical comedy.

Foundation of the Friendship

Both boys became part of Logan’s close childhood circle with Malik and Jordan. By third grade, all five were established as friends. James attended Baltimore School for the Arts, while Mason attended Edgewood High School, but they remained connected through group messages and gatherings.

Dynamics and Communication

Mason and James committed fully to jokes together, flicking popcorn at more serious friends and turning ordinary gatherings into collaborative bits. Mason also flirted openly with James as part of their long-running banter. James’s relationship with Charlotte Hargreaves did not stop Mason from joking that he was next in line or telling James to pass along his greetings to her.

Their physicality matched the rest of Mason’s friendships: casual shoulder contact, jostling, and exaggerated movement were ordinary parts of their group presence rather than formal declarations of affection.

Shared History and Milestones

After Jacob’s seizure and cardiac arrest, Mason and James joined the group’s FaceTime call with Logan. Both agreed to help make the group a dependable support network for Jacob.

In February 2024, Mason and James joined the full Ride-or-Dies group on Logan’s sixteenth-birthday Caribbean cruise.

In 2025, James attended Edgewood’s graduation as a guest to support Mason and the other graduates. Later that summer, both attended the Weston family’s barbecue before James left for NYU Tisch School of the Arts and Mason remained in Baltimore, Maryland.

Relationships Friendships Mason Brooks James Pennington