Sidney Leroy
Strickland, Jr.

01 / Origins

A Mind of His Own

From Redlands, into the world, and home again.

Sidney Leroy Strickland, Jr. lived a life defined by an extraordinary mind, an independent spirit, an unwavering devotion to family, and a deeply held belief in standing up for what was right. An engineer by training who chose law on a matter of conscience, he rose to become Secretary of the Interstate Commerce Commission and one of the country’s leading attorneys in railroad and surface transportation law. Yet those who knew him best remember just as readily his quick, dry wit, his generosity, his fierce loyalty, and his ability to treat everyone with the same respect, regardless of title or circumstance.

Sidney died on September 8, 2026, in Redlands, California, the community where he was raised and where so much of his story began. He was 76.

Sidney was born May 21, 1950, in Bryn Mawr, California, to Sidney Strickland, Sr. and Arvine Prudhomme Strickland — known to family and friends as “Red” — and grew up in Redlands. He spent part of his childhood in what he called “the projects” of Redlands, before his mother remarried and the family settled on Sharon Road. A gifted student, Sidney earned straight A’s and excelled at Redlands High School, where he competed as a sprinter and high jumper on the track team, setting school records at the time. He also boxed, beginning a lifelong love of the sport.

Recruited by Harvard and Yale while in high school, Sidney chose to remain closer to home, initially attending the University of Redlands before transferring to the University of California, Berkeley. He loved Berkeley, maintained friendships from those years throughout his life, and earned a Bachelor of Science in engineering in 1972.

It was an engineering internship that changed the course of his life. Assigned to calculate how deep an excavation had to be, Sidney came to understand that the work was in service of weapons testing — how deep a bomb had to be buried so that the blast would not reach the surrounding population. Although he had the ability to do the work, he decided that was not how he wanted to use his mind. He turned instead to law, earning his Juris Doctor from the University of California, Davis, School of Law in 1975.

03 / Character

A Life Lived on His Own Terms

The distance he traveled mattered less than the principles he carried.

For all that he accomplished, Sidney remained remarkably unpretentious. He could be the most book-smart person in a room and the least likely to look down on anyone in it. Titles and status meant little to him; he treated a janitor with the same respect he gave a judge and remained loyal to friends from every chapter and walk of life. He kept friends for decades and rarely missed the opportunity to send an old friend or relative a birthday message. He gave legal advice freely, opened his home to relatives and close family friends who needed somewhere to land, and continued offering his family advice, encouragement and help throughout his life. He was frugal about himself but generous with the people he loved.

Having spent part of his childhood in “the projects” of Redlands, Sidney took particular pride in moving his own family to Woodmore, one of the Washington region’s most prominent communities of Black affluence. It was a quiet measure of how far he had traveled from where he began — and of his determination that his children would have opportunities and comforts he had not always known himself.

His formidable intelligence was accompanied by endless curiosity. As a boy, Sidney took apart his toys almost as soon as he received them because he wanted to understand how they worked. As an adult, there was always something to tinker with or repair — cars, electronics or whatever else captured his attention. He seemed equally at home discussing mathematics and science, history, politics or law. Current events were a constant in his life, and he attended political conventions, presidential inaugurations, fundraisers, White House and congressional events, developing friendships throughout the political and professional world.

Sidney was also hilarious, with a quick, dry wit his children inherited. He was stubborn, proud and loved a good debate. His children were encouraged to argue back: if they could make their case, he would listen. He taught them to think independently, question authority, stand tall in the face of racism and stand up for what they believed was right. Education, he reminded them, was something no one could take from them. Don’t follow the pack. Lead it.