James A. Drill

James Andrew Drill (1936-2026) beloved husband, father, grandfather, great-grandfather, brother, attorney, mentor, and friend, passed away peacefully surrounded by loved ones.

Jim lived a remarkable life defined by family, love, hard work, accomplishment, service, and an enduring commitment to others. He was a man of strong character and conviction who took great pride in the life he built and, above all, in the family he and his beloved wife, Jane Ann, created together.

A Love Story of 69 Years

Jim was a devoted husband to his loving wife, Jane Ann (Fox) Drill, with whom he shared an extraordinary 69 years of marriage.

Their life together was a testament to enduring love, partnership, commitment, and family. Through nearly seven decades, Jim and Jane Ann shared life’s greatest joys and challenges, raised a large and close-knit family, celebrated countless milestones, and created a lifetime of memories.

While Jim accomplished much throughout his professional life, his family remained at the center of it. He was a loving and devoted husband and a proud father who took tremendous joy in the lives of his children, grandchildren, and great-grandchildren.

An Illustrious Career as a Trial Lawyer

Jim dedicated more than six decades of his life to the practice of law and became widely respected as an accomplished trial lawyer and passionate advocate for people who had been injured or wronged.

He earned his B.B.A. from the University of Wisconsin–Madison in 1959 and graduated from the University of Wisconsin Law School in 1961. From his first days in law school, Jim knew he wanted to become a trial lawyer and represent people seeking justice in the courtroom.

That calling brought him to New Richmond in 1961, when he joined Doar & Knowles, a law firm whose roots in the community stretched back to 1883. The firm had already been shaped by generations of distinguished Wisconsin lawyers and public servants, including W.T. Doar and future Wisconsin Governor Warren P. Knowles. In time, Jim would become an important part of that history, and the firm would eventually become known as Doar, Drill & Skow.

Jim built his practice primarily around representing injured people and their families. His cases arose from automobile and machinery accidents, medical malpractice, and other serious injuries. He advocated for his clients before juries, trial judges, and appellate courts in both state and federal court systems.

Jim’s approach to the law reflected many of the qualities that defined him throughout his life: preparation, persistence, intelligence, determination, and a deeply held belief in standing up for people who needed an advocate.

He became a formidable courtroom lawyer, but his career was about more than winning cases. He understood the responsibility that came with representing people and families during some of the most difficult moments of their lives.

His influence eventually reached far beyond his own courtroom practice. Jim served in leadership roles within the legal profession, including as President of the Wisconsin Academy of Trial Lawyers and as a member of the Wisconsin Judicial Council. His professional affiliations also included the American Association for Justice, Association of Trial Lawyers of America, American Board of Trial Advocates, Wisconsin Association for Justice, State Bar of Wisconsin, American Bar Association, and St. Croix Valley Bar Association.

Jim was also an author and teacher. He wrote A Systems Approach to Personal Injury Litigation and frequently lectured other lawyers about personal injury litigation, sharing knowledge accumulated through decades of courtroom experience.

His commitment to service extended beyond the legal profession. Jim served his community as a member of the New Richmond City Council, reflecting a tradition of public service that had long been part of the firm he joined as a young lawyer.

Over the years, Jim received numerous professional honors and recognition, including recognition by Wisconsin Super Lawyers and Best Lawyers in America.

Perhaps one of the most meaningful parts of Jim’s professional legacy was that the connection between his family and the law did not end with him. His daughter, Lisa M. Drill (Cichy) followed him into the legal profession and became an attorney at Doar, Drill & Skow, carrying the Drill name and a family tradition of advocacy into another generation. His daughter, Jennifer Drill (Lutz) also obtained her law degree.

After more than 60 years in the practice of law, Jim became Attornatus Emeritus at Doar, Drill & Skow. His name remains woven into the history of a firm that has served New Richmond and western Wisconsin for generations.

For Jim, being a lawyer was more than a profession. It was a calling — an opportunity to advocate for others, seek justice, serve his community, and give people a voice when they needed one most.

His Greatest Accomplishment: His Family

Jim leaves behind a remarkable legacy.

Part of that legacy can be found in a legal career spanning more than six decades, in the clients for whom he fought, in the lawyers he taught and influenced, in the community he served, and in a respected New Richmond law firm that still bears his name.

For all that Jim accomplished professionally, the achievement that mattered most to him was the family he and Jane Ann, his wife and partner through 69 years of life, built together. It is in their 7 children, 21 grandchildren, and 6 great-grandchildren. It is in the stories they tell, the traditions they continue, the lessons they carry with them, and the love of family that Jim and Jane Ann placed at the center of their life together.

Jim and Jane Ann raised seven children:

Peter Drill; Lisa Drill Cichy(Steve); Andrew Drill (Stacy); Mary Drill Hermanek (John); John Drill; James (Gump) Drill; and Jennifer Drill Lutz (Lon).

Jim and Jane Ann have 21 grandchildren and 6 great-grandchildren

Jim took enormous pride in watching his family grow. He delighted in their accomplishments, personalities, adventures, and the individual lives of each one of them. Family gatherings, storytelling, traditions, celebrations, and simple time spent together at the lake became the most meaningful parts of his life.

Away from his work, Jim enjoyed hunting, fishing, and watching kids play sports.

His Roots

Jim was born in Princeton, WI, the son of Victor Drill and Dolores (Airoldi) Drill. His older sister, Donna (Drill) Drexler still lives in Manitowoc WI.

His life was long and full. His accomplishments were many. But his greatest legacy will always be his family. His family and friends will deeply miss him, but they will carry forward the lessons he taught, the stories he shared, the standards he set, and the love he gave them.

Memorial Mass of Christian Burial will be Tues, Sept 8, 2026 at 12 noon at Immaculate Conception Catholic Church, 151 S Washington Ave, New Richmond, Wisconsin. Visitation will be from 10:30-12:00 at the church. Luncheon to follow at the church.  The service will be livestreamed.  Link for the livestream will be updated soon.

Arrangements by Bakken-Young Funeral & Cremation Services. In memoriam, the family encourages gifts to a charity of your choosing.