Jeff Scott Olson has argued a legal case in front of the U.S. Supreme Court in Washington, D.C., and participated in an Ernest Hemingway look-alike contest in Key West, Florida.
In neither instance did he win, which did not affect Olson’s essential good nature.
The Madison attorney left Sloppy Joe’s bar in Key West convinced the Hemingway contest was weighted against first-timers, so maybe he’d try again.
When Olson left the Supreme Court building—the decision in his case still months away—he walked onto the marble steps and was immediately confronted by dozens of reporters and television cameras.
For a moment, Olson wondered how his representation of a Milwaukee adult bookstore could have drawn such a throng on this late November day in 2000. Then it dawned on him: That day was the deadline for the filing of legal briefs by attorneys involved in Bush v. Gore, which would determine who would occupy the White House. The media was out in force hoping to get comments from the lawyers on both sides. Olson chuckled at the thought that the crowd was there for his case. He can find humor in most things, including himself.
Do not, however, mistake that for a lack of seriousness about the law.
Olson, 67, is one of Wisconsin’s premier civil rights attorneys, a pioneer in a field that was new when he started practicing law four decades ago. Employment discrimination, housing discrimination—you’d better be good when you’re litigating under laws that a few years earlier weren’t even on the books.
Olson is best known today for two cases—his firm’s successful representation of the families of Paul Heenan, and Ashley DiPiazza (with lead attorney Andrea Farrell). Each was fatally shot by Madison police officers in separate incidents—Heenan in 2012 and DiPiazza in 2014.
Olson brought federal lawsuits alleging that police used unreasonable force. He won a $2.3 million settlement in the Heenan case in 2015 and a $7 million jury verdict, subject to appeal, earlier this year in the DiPiazza case.
While Olson would like to see American police training protocols on the use of deadly force changed, he doesn’t single out the Madison department.
“I think there was an unfortunate cluster of bad [police] shootings over the course of about three years in Madison,” he says. “During that time, there were some unquestionably good and righteous shootings.”
The attorney continues: “The [Madison] officers, generally speaking, are pretty good. They’re pretty restrained. They’re pretty cool under pressure. Not all of them, but almost all of them. I think we’ll probably go a long time in Madison before we see a police shooting that gets turned into a successful civil rights claim.”
Olson grew up in Augusta, southeast of Eau Claire, the son of a rural mail carrier and a beautician. In 1968 he enrolled at the University of Wisconsin–Madison, majoring in sociology primarily because it wasn’t math or physics. With his degree, Olson went to Yale for a year of graduate school, which turned out to be enough sociology. He came back to Madison and entered law school in fall 1973.
In contracts class his first semester, Olson made one of the enduring friendships of his life. A student approached and said, “I understand you play the fiddle.”
“You’ve been misinformed,” Olson replied. “It’s banjo.”
Olson and Mike Fox have been playing music together ever since. Fox plays guitar and is a distinguished civil trial attorney himself. They’ve also worked together—Fox was co-counsel on the Heenan case.
In between his second and third years in law school, Olson went home for the summer and worked for a highly regarded litigation firm in Eau Claire.
“I got lucky,” he says. “I learned how to treat the people who work for you. They treated me like visiting royalty. And I learned I didn’t want to practice law in a small Wisconsin city.”
Instead, Olson went to work in Madison for Percy L. Julian Jr.—for whom he’d clerked—and got a front-row seat to the early days of civil rights law.
“At that point, Percy was the only civil rights lawyer in Madison, and one of the only black lawyers,” Olson says. “He was strongly affiliated with the NAACP Legal Defense Fund.”
Olson helped Julian—who died in 2008—in class action suits alleging race and sex discrimination. Julian was lead counsel in the 1970s school desegregation case in Springfield, Illinois.
“We’d get on a private plane and fly down to Springfield for court appearances,” Olson says.
The cases appealed to Olson’s sense of social justice and natural affinity for the underdog.
“So much of my career is unashamedly copied on Percy Julian,” he says.
Olson established a solo practice in 1994 and today employs attorney Farrell and trial consultant Sarah Crandall. Crandall spent years as a criminal defense attorney in Madison and has been a friend of Olson’s for decades.
A lifelong bachelor, Olson has many admiring friends, and not just because he’s happy to take them out on the boat he keeps docked outside his condo on Lake Monona, where he has a fast draw on the beer cooler.
They admire how Olson has fought the good fight for 40 years with no intention of slowing down.
“I love going to work,” he says. “I’ve got plenty to do.”
Doug Moe is a Madison writer and a former editor of Madison Magazine. Read his weekly blog, “Doug Moe’s Madison,” on madisonmagazine.com.