March 1, 2023 – Judge Gary Sherman said it was his gift for a particular form of gab that led him the University of Wisconsin Law School.
Sherman’s grandfather practiced law on the Loop in downtown Chicago, but Sherman’s father became a real estate developer instead of a lawyer.
“They wanted my dad to go to law school, but he didn’t want to and it was always a family struggle,” Sherman said. “One day at dinner we were talking and my stepfather said, ‘You like to argue a lot, you should go to law school,’ so I did.”
Sherman, who grew up on the north side of Chicago, obtained his undergraduate degree at U.W.-Madison in 1970. His four years as an undergraduate coincided with the height of social unrest on campus.
“I shouldn’t admit this in public, but it was pretty exciting,” Sherman said. “There was a spirit. Major changes happened because of it.”
Sherman cited an event that took place in 1967, his sophomore year. Black students walked out on strike, demanding that the university establish ethnic studies programs.
“They shut the campus down,” Sherman said. “I remember standing in front of a door with a bunch of other students to secure the building. A lot of people believed in it.”
Distant Early Warning
When Sherman graduated from college, the military draft was still in place. To avoid going to Vietnam, he enrolled in the Reserve Officer Training Corps.
Jeff M. Brown is a legal writer for the State Bar of Wisconsin, Madison. He can be reached by email or by phone at (608) 250-6126.
“If you wanted to go to law school, you had to find a way to avoid going to Vietnam,” Sherman said. “The Air Force told me they would defer my active duty to allow me to finish law school, so I did that.”
When Sherman graduated with his J.D. in the spring of 1973, the Air Force sent him to a base in Duluth, Minn.
The base, which was home to a squadron of high-altitude interceptors, was located close to a string of distant early warning radar stations along the U.S.-Canada border.
The radar stations were designed to detect Soviet nuclear bombers winging over the North Pole.
“They reported their data to a giant computer in Duluth,” Sherman said. “That was the mission for the base.”
Sherman was one of seven lawyers on the base. They advised the base commander on matters from procurement to discipline and helped the members of the military with a variety of legal problems.
“Military personnel change stations at the whim of the military,” Sherman said. “So, you’ll sign a lease and then before you thought you would, you’re being sent to some other place. Then your lease would be a problem, or your car contract.”
Sherman barely had time to get his feet wet as an Air Force lawyer. As the war in Vietnam wound down, the military began shedding personnel.
“They really pumped up the number of officers that they thought they would need when the war as going on and then they had all these officers they didn’t need,” Sherman said. “And among the other things they didn’t need, were lawyers.”
Sherman served only 92 days in the Air Force, followed by four years of inactive reserve. He wasn’t even in long enough to get a regulation haircut.
“They all sort of figured out that I was a hippie,” Sherman said. “Once in a while, my commanding officer would say “I’m going for a haircut, would you like to come with?’”
Small Town Practice
After being discharged by the Air Force, Sherman moved to Washburn, a city of 2,000 in Bayfield County on the shores of Lake Superior’s Chequamegon Bay.
He moved to Washburn because his wife was from Herbster, located 28 miles from Washburn.
“We would go home on breaks from law school to visit her family and we got to know a bunch of people our age, and we became friends and became part of their community,” Sherman said.
In Washburn, Sherman worked for a small firm for nine months before hanging out his shingle.
He did almost every type of law except contested divorces and plaintiff’s side personal injury. Over the years, Sherman came to concentrate on municipal law, especially sewer and water systems.
“You could say I built most of the sewer and water systems in northwest Wisconsin,” Sherman said.
When they moved to Washburn, Sherman and his wife bought 160 acres of land. They didn’t have much money left over to build a house.
“We built a little shack,” Sherman said. “It was 14x20 and was very crude. We lived in it for two or three years while we were building our house.”
Sherman said he and his wife were part of “a scene” in Bayfield County that was sparked by an influx of idealistic young people.
“If I were a better writer, I would have written a book like On the Road,” said Sherman, referring to Jack Kerouac’s Beat Generation classic.
“It was like something out of a book,” Sherman said.
Sherman’s practice kept him busy. But he didn’t like the desk work.
“I never liked to just sit in the office and practice law,” Sherman said. “So, over the years I did a number of things whose primary motivation was to distract me, to get me out of the office.”
One of those things was writing a new edition of the Wisconsin Methods of Practice, a three-volume set, published by West Publishing (West), that Sherman described as “the standard cookbook on how to practice law in Wisconsin.”
As a young lawyer, Sherman found Wisconsin Methods of Practice invaluable. After several years of not receiving pocket parts (paper updates designed to be slipped into the back cover of the book), Sherman called an editor at West.
Sherman thought he’d been mistakenly removed from the subscriber list. Instead, the editor told Sherman that he wasn’t receiving pocket parts because West had stopped producing them – they had nobody to write the updates.
Furthermore, the editor said, Wisconsin Methods of Practice needed a complete re-write.
“I said, ‘If you give me at least three years, I’ll do it.’ So, I did it.”
Sherman fit some of the writing in around his practice and family life. Other times, he took whole months off from his practice.
He wrote part of the book over one winter, in Chicago.
Sherman’s mother and stepfather, newly retired, decamped to Florida for the winter. Sherman took over their Chicago house and convinced his grandfather’s law partner to loan him an office in a building on the Loop so he could work on Wisconsin Practice.
“I would go downtown on the train every day and go to the office and work just like the other lawyers in the office tower,” Sherman said.
Board of Governors, President
Another thing Sherman did to get out of the office was to run for the State Bar’s president-elect position in 1992.
Sherman had served two terms on the State Bar's Board of Governors, beginning in the 1980s. He served as president for the 1994-1995 term.
“It was a wonderful experience, partly because of the staff,” Sherman said. “They were really important people.”
Sherman’s tenure coincided with the computerization of the practice of law.
The State Bar established a relationship with a company that specialized in computerized legal research, partnered with West to make legal materials available on CDs to members at a reduced cost, and launched an award-winning website.
“We really took the lead in law office automation,” Sherman said.
On the Campaign Trail
After finishing his term as past president of the State Bar, Sherman mounted a campaign for an open seat on the Wisconsin Court of Appeals District III.
During the campaign, Sherman crisscrossed the district, which included 35 counties, and spent $120,000 of his own money. He lost by 10 points.
After the election loss, Sherman got a call from George Brown, the State Bar’s lobbyist (Brown later became the State Bar’s executive director). Brown told Sherman that the legislator from Sherman’s Assembly district was retiring.
Sherman decided to run for the seat. Relying on the name recognition that he’d built up during the appeals court campaign, Sherman won. He represented the 74th District in the Assembly as a Democrat from 1999 to 2009.
During his tenure in the legislature, Sherman served on the powerful Joint Finance Committee. He also co-chaired the Assembly Democratic Campaign Committee and traveled around the state on behalf of his party’s Assembly candidates.
“I got used to sleeping on people’s couches and in their basements,” Sherman said.
Dons the Black Robe
In 2010, Governor Jim Doyle appointed Sherman to the Wisconsin Court of Appeals District IV.
Like the other 15 court of appeals judges, Sherman served on three three-judge panels. Together, the court of appeals judges heard and disposed of 3,000 cases per year.
“It’s the hardest work I’ve ever had in my life,” Sherman said.
According to Sherman, the collaboration with his fellow judges made the hard work worth it.
“We would spend a week reading briefs and making notes, and then once a month we’d meet for three days as a panel,” Sherman said.
Each judge, Sherman said, prepared 21 cases per month. The panel would then reach a tentative decision in each case and assign it for writing, with staff lawyers writing the per curiam opinions.
Sherman now splits his time between northern Wisconsin and Tucson, Arizona, spending winters in the latter state.
“I’m as retired as retired can be,” Sherman said.
He keeps his legal feet wet by serving as a court commissioner in Bayfield County.
“The local judge prevailed upon me to do that,” Sherman said.
Sherman spends his time in Tucson reading and with friends.
A favorite summer activity for Sherman is attending string quartet concerts on Madeline Island.
“I’ve never been one to sit still and just do one thing,” Sherman said. “I’ve had lots of opportunities in my life to do pretty interesting things.”