The Masterson Family Sponsors the 2026 Diamond Bra: Most Inspirational, In Every Way

There are supporters… and then there are families who become part of the very fabric of The Boob Ride. For 2026 — our final ride — we are deeply honored to announce that the Masterson Family is sponsoring the Diamond Bra (Most Inspirational) award. It’s hard to imagine a more fitting match.

A Boob Ride Family Since 2015

The extended Masterson Family has been essential to The Boob Ride community for more than a decade. Since 2015, they’ve shown up year after year as riders, volunteers, sponsors, cheerleaders, and steadfast supporters. They are the kind of family that doesn’t just attend events — they anchor them. Their story with The Boob Ride began when Marianne Masterson and Cathy Orchard met Jennifer Carey during the 2015 Susan G. Komen 3Day Walk. That meeting sparked a connection rooted in shared purpose, compassion, and an unshakable commitment to helping others affected by breast cancer. From that point forward, the Masterson family didn’t just support Fun 4 Good — they helped shape it.

Leadership, Service, and Showing Up

Marianne went on to join the Fun 4 Good Board of Directors, bringing her heart, leadership, and lived experience to the organization. Cathy became one of those volunteers every nonprofit dreams of — instrumental, reliable, and endlessly generous with her time and energy for many years. And it didn’t stop with them. Marianne and Cathy’s children, siblings, and extended family members consistently came out to volunteer, support riders, staff rest stops, and cheer at finish lines. Year after year, they showed us what it looks like when a cause becomes personal — and when a family turns care into action.

Team STRIDE: Born from Purpose, Powered by Family

Long before The Boob Ride, Cathy and Marianne helped form Team STRIDE in 2010 for the Susan G. Komen 3Day Walk in San Diego. What started as a team quickly became a movement rooted in love, resilience, and awareness. Marianne is one of eleven siblings — seven of them sisters — and heartbreakingly, all seven sisters have been directly impacted by breast cancer. Despite extensive testing, every sister tested negative for the breast cancer gene, making their shared diagnosis even more devastating and confounding. Cancer is cruel in any form, but this reality is especially devastating. Marianne’s doctor put it plainly: given her family history, it isn’t a matter of if she will get breast cancer — it’s a matter of when. And yet, the story does not end in fear.

Hope, Even After Loss

The sisters, their families, and their supporters continue to move forward with determination and hope. Through Team STRIDE, they remain deeply committed to raising funds and awareness for a disease that has taken so much — including their beloved sister Sheila. Their advocacy honors Sheila’s memory and fuels a mission to ensure no one faces breast cancer alone.

Why the Diamond Bra Matters

The Diamond Bra (Most Inspirational) recognizes individuals and stories that embody courage, perseverance, and the power of community. The Masterson Family represents all of that — and more. Their sponsorship is not just generous. It is deeply personal. It is a reflection of lived experience, service, leadership, and love stretched across years of action.

As we approach the final Boob Ride in 2026, we are profoundly grateful to celebrate this family — not only for sponsoring the Diamond Bra, but for reminding all of us why we ride, why we volunteer, and why we keep showing up.

Thank you, Masterson Family.
You inspire us — always.