This article was reported and written in a collaboration with ProPublica, the nonprofit investigative journalism organization.

WOLF POINT, Mont. — Every day Ron Jackson walks into work and is reminded of his failures.

As Mr. Jackson, the warden of the Fort Peck Indian Reservation adult correctional facility, patrols the cells, he sees Native American inmates who might be leading productive lives on the outside if they had graduated from high school. And Mr. Jackson, a member of the Assiniboine tribe, says he feels partly responsible.

Before becoming warden, he served on the Wolf Point school board for 15 years, 10 as its chairman. He pushed to curb discrimination in the town’s schools against Native Americans, who make up more than half of students but less than one-fifth of the staff. He fought for more reading instruction and other support for Native children and challenged decisions to expel them. But his efforts mostly fell flat as the white majority on the board outvoted or ignored him.