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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 Ride-or-Dies’ 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, dramatic movement, and retellings of academic mishaps; Mason supplied trash talk, deadpan absurdity, and physical comedy. Their timing gave the group entertainment and relief during periods of academic and personal pressure.

Foundation of the Friendship

Mason became friends with Logan, Malik, and Jordan in second grade at a Baltimore gifted academy. James joined in third grade after immigrating from England, completing the five-person circle. James later attended Baltimore School for the Arts, while Mason attended Edgewood High School. Group messages and gatherings kept them connected across the different school schedules.

Dynamics and Communication

James could reenact an academic disaster with wild arm flails and enough dramatic flair “to warrant an Oscar.” At senior-year lunches, Mason answered with deadpan observations; the pair’s timing could leave the others wheezing with laughter. They flicked popcorn at their more serious friends, committed fully to each other’s jokes, and turned ordinary gatherings into collaborative bits. During a time of college applications, scholarship essays, and high expectations, the humor offered the group emotional release as well as entertainment.

Mason also flirted 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 saying, “Tell Charlotte I said hi… or don’t.” The flirtation was playful and affectionate rather than a proposal to change their friendship.

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. The ease with which they could be silly, affectionate, or emotionally open gave both room to resist narrower expectations about how male friends should behave.

Cultural Context

Mason, who was American-born, and James, who immigrated from England, belonged to a friend group whose other three members were Black. Their place in the group came from years of shared life rather than an assumption that their White identities gave them the same experiences as Logan, Malik, or Jordan. Mason grew up near the rhythms and references of Black Baltimore; James learned American racial dynamics through his friends while retaining his British family culture and accent.

Their comedy gave the group room to laugh amid pressures that included racism, bullying, and the expectation of exceptional academic performance. Mason could poke at Logan’s untouched food while James turned an academic mishap into a dramatic reenactment. These moments let the friends enjoy being teenagers together without erasing the unequal treatment around them. Mason and James both spoke up when Logan was bullied and witnessed racist treatment of their friends, including a tense police encounter remembered within the group. James later identified one disparity when Jordan reported that a counselor had told him to “reconsider aiming too high”: “Logan doesn’t get that talk.” Their awareness came through proximity and loyalty, not through direct experience of anti-Black racism.

Mason’s open flirtation, their physical comedy, and James’s comfort with affection and tears also made their friendship less constrained by conventional British or American expectations of masculine reserve. Their particular group allowed those forms of expression without making either boy defend the closeness of the friendship.

Shared History and Milestones

During Logan’s bullying years, from third through eighth grade, Mason and James helped defend him. Both tried speaking up about the harassment, but adults did not reliably act. They used humor alongside direct support; for Mason, the dismissal of his efforts on Logan’s behalf later made him fear that reporting bullying about his own body would invite ridicule.

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

In late spring 2025, James attended Edgewood’s graduation as a guest to support Mason and the other graduates, though he graduated from Baltimore School for the Arts. Both witnessed the group’s achievement after difficult school years. 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