He then attended the University of South Dakota School of Law, graduating magna cum laude in 1962 with a Juris Doctor.

Wollman served for fifteen years on the Supreme Court of South Dakota, including as chief justice from 1978 to 1982.

[3] Wollman was nominated by President Ronald Reagan on June 25, 1985, to the United States Court of Appeals for the Eighth Circuit, to a new seat created by 98 Stat.

South Dakota senior senator Larry Pressler worked with the White House to secure this nomination, and recommended Wollman as a conservative judge.

On February 9, 2018, Wollman notified President Donald Trump that he intended to step down as an active judge no later than the end of 2018.