top of page


In the world of charitable organizations and selfless acts, there are individuals who shine bright, embodying the spirit of compassion and dedication. One such shining star is Drenden Rainey, whose journey led to him becoming an honorary member of the Masked Athlete Team (MAT) at our 2024 gala.  This story not only reflects Dre's commitment but also highlights the profound impact of his parents, Josh and Jennifer, within the Operation Enduring Warrior family.


Josh Rainey, Dre's father, is an integral part of the Operation Enduring Warrior (OEW) family. As a proud member, Josh has consistently demonstrated the power of volunteering, showcasing how one individual can contribute to the greater good. His mother, Jennifer, has given countless hours supporting the team and Josh's efforts to support honorees. Growing up with parents actively involved in OEW, Dre Rainey witnessed firsthand the transformative impact of volunteering. Josh Rainey not only dedicated his time but also instilled in his son the values of empathy, selflessness, and the importance of giving back to the community. As a result, Dre developed a passion for making a positive impact on the lives of others.


Dre Rainey's dedication and enthusiasm for supporting the Masked Athlete Team became evident during the pre-gala fitness event. Dre's willingness to go above and beyond in assisting the team did not go unnoticed, setting the stage for a remarkable recognition.  In a heartwarming gesture, the Masked Athlete Team decided to honor Dre Rainey by inviting him to join their esteemed ranks as an honorary member. This recognition at our 2024 gala is a testament to Dre's outstanding contributions, his dedication to the mission of OEW, and his embodiment of the values that MAT holds dear.


Dre Rainey, now an honorary member of the Masked Athlete Team, is poised to continue making a significant impact within the OEW community and shows that everyone can make an impact on the lives of our honorees and our team members. His journey is an inspiring example of how a family's commitment to service can shape the values of the next generation and contribute to a collective effort to make the world a better place.


Dre Rainey's induction as an honorary member of the Masked Athlete Team is a celebration of not only his individual efforts but also the legacy of service instilled by his parents, Josh and Jennifer. As we applaud Dre for his dedication, let us be reminded of the ripple effect that acts of kindness and selflessness can have, inspiring others to join the noble cause of making a positive impact in our communities.


Do you want to learn more about how to volunteer?  Visit HERE:

130 views0 comments

OEW was saddened recently when we learned of the passing of Stephen Raymond, father to Weyland Raymond, one of OEW’s most dedicated sponsors and close friends. Weyland and his wife Mandi have supported OEW for many years both financially and through in-person support.

Wayland and Mandi Thank you for your donation in memory of your father and on behalf of all of OEW please accept our heartfelt condolences on your loss.

In Waylands Words:

Stephen Elliot Raymond was born in Brookline, MA 14FEB42 to First Generation Americans that immigrated from Russia & Germany.

Enlisting in the United States Navy 12JUN62, my Father was ultimately one of the Navy Seamen that photographed and worked extensively with NASA’s ( and the Navy’s ) efforts back in the day. My father was one of the U.S. Navy Sailors that documented the recovery of the crew capsule and took the iconic photographs of Alan Shepherd’s boots having “footprints” painted around them as he stood on the recovery deck of the USS Lake Champlain, after recovering Freedom 7. He documented many, MANY other missions, as well.

From his time in the Navy, working and documenting the Space Program, capturing the missions & recoveries of the capsules, to striking out on his own to start his own business(es) when no one else thought he should or could, exemplifying what it meant to be his own man and work for himself, to opening his arms and house to an asshole young kid that was living on the street, and then taking responsibility for him at a time when the courts were against men having custody at all. He and his wife even adopted another child later in life, giving that girl love and a chance. She’s now a doctor and doing well.

Stephen Elliot Raymond passed away on Thursday, 18JAN24, in Fort Lauderdale, Florida at the age of 81. He is survived by his Wife Donna, his Son Weyland (married to Mandi), his Daughter Deann (married to Garven). He was recently buried at the South Florida National Cemetery in Lake Worth, Florida.

Kiss the people you love. Be thankful for what you have. Be kind, respectful, open handed, and generous. You might not get a second chance.



American Machine & Gear Works

Milwaukee, Wisconsin

"When it HAS to be right, make sure it's American!"

10 views0 comments

As we wrap up our 10-year anniversary, we celebrate with our 2023 Holiday Letter.

Enjoy this read and we look forward to seeing you in 2024.

Holiday Letter 2023
Download PDF • 648KB

16 views0 comments
bottom of page