“A Minnesota attorney grounded in fairness and law”
Jonathan Woolsey is an American attorney whose legal career reflects a deep commitment to the principles of fairness, diligence, and the rule of law. Based in Chaska, Minnesota, Woolsey has spent more than a decade working across multiple areas of legal practice, including workers’ compensation, litigation, corporate law, and public service. While he may be best known to the public for his 2024 candidacy for the Minnesota Court of Appeals, his professional story extends far beyond that single race.
Key Facts About Jonathan Woolsey
| Field | Details |
|---|---|
| Full Name | Jonathan Woolsey |
| Known For | Minnesota attorney and 2024 judicial candidate |
| Profession | Attorney |
| Based In | Chaska, Minnesota, USA |
| Bar Admission | Minnesota Bar (2011) |
| Education | University of St. Thomas (Bachelor’s), William Mitchell College of Law (J.D.) |
| Legal Specialties | Workers’ compensation, civil litigation, corporate law |
| Current Role | Corporate Counsel at InfoSync (since 2023) |
| Judicial Campaign | Minnesota Court of Appeals, District 12 (2024) |
| Election Outcome | Lost to Judge Diane B. Bratvold |
| Years Active | 2011–present |
Early Life and Educational Foundation
Jonathan Woolsey completed his undergraduate studies at the University of St. Thomas, where he earned his bachelor’s degree in the mid-2000s. While year is not publicly listed, his academic timeline aligns with his entry into legal profession.
He went on to earn his Juris Doctor from William Mitchell College of Law, now part of Mitchell Hamline School of Law. Although his graduation year is not publicly documented, he was admitted to the Minnesota Bar in 2011, indicating he completed law school around 2010 or 2011.
During law school, Woolsey gained practical legal experience by clerking for a workers’ compensation attorney and serving as a certified student attorney with the First District Public Defender, preparing him for a professional legal career.
Entering the Legal Profession
Jonathan Woolsey was admitted to the Minnesota Bar in 2011, officially beginning his professional legal career. He started practicing law in the Twin Cities area, where he joined a mid-sized Minneapolis firm that specialized in workers’ compensation and insurance-related litigation.
This early phase of his career gave him deep insight into Minnesota’s workers’ compensation system. He represented employers and insurers, handling claims related to workplace injuries, medical benefits, and disability disputes.
Working on these claims also provided him with a balanced understanding of both employee and employer perspectives. Even while representing companies and insurers, he was required to evaluate medical evidence, legal standards, and the human realities of workplace injury.
Developing a Broad Legal Skill Set
As his career progressed, Woolsey expanded beyond workers’ compensation into broader areas of litigation and legal support. His early background in criminal defense during law school allowed him to maintain familiarity with the criminal justice system, while his workers’ compensation work gave him extensive experience in civil law.
Over time, he moved into contract-based legal roles for various government agencies. In these positions, Woolsey worked on compliance, document review, and regulatory matters. These assignments allowed him to see how legal systems function at the administrative and policy level.
He also served as an eDiscovery client manager at Thomson Reuters, one of the world’s leading providers of legal and financial information. In this role, Woolsey worked with law firms and organizations to manage digital evidence, litigation data, and legal technology systems.
Transition to Corporate Counsel
In March 2023, Jonathan Woolsey took on a new role as Corporate Counsel for InfoSync, an outsourcing firm that specializes in accounting and payroll services. This marked a significant shift from traditional litigation into corporate legal leadership.
As corporate counsel, Woolsey became responsible for advising on contracts, regulatory compliance, risk management, and business operations. Rather than focusing on individual disputes, his role involved helping a growing company operate within legal boundaries while expanding its services.
Corporate law requires a different set of skills than courtroom litigation. It involves anticipating problems before they occur, ensuring agreements are properly drafted, and protecting both the company and its clients. Woolsey’s background in litigation, government compliance, and eDiscovery made him well suited to this responsibility.
This phase of his career highlights his versatility as an attorney, someone capable of moving between advocacy, analysis, and business-oriented legal strategy.
Judicial Candidacy in 2024
Jonathan Woolsey became more widely known to the public in 2024 when he ran for a seat on the Minnesota Court of Appeals, District 12. He challenged incumbent Judge Diane B. Bratvold in a race that attracted attention within Minnesota’s legal community.
Although Woolsey did not win the election, his decision to run was rooted in his belief in the importance of judicial independence and strict adherence to the rule of law. In his campaign materials, he emphasized that judges must apply the law impartially, without political influence or personal bias.
Attorney polls showed overwhelming support for the incumbent, and Woolsey’s campaign faced long odds. Nevertheless, his candidacy reflected a willingness to engage in the democratic process and to put his legal philosophy before the public.
Commitment to Legal Education and Public Understanding
Beyond his formal legal roles, Jonathan Woolsey has contributed to the legal field through writing and informal education. He has maintained a personal blog focused on Minnesota workers’ compensation law, where he explains technical topics in a clear and accessible way.
Subjects such as intervention rights, benefit calculations, and procedural rules can be confusing even for legal professionals. By breaking these issues down into practical explanations, Woolsey has helped students, attorneys, and interested readers better understand how the system works.
This educational outreach reflects an important aspect of his professional identity: a belief that law should not be hidden behind unnecessary complexity. Making legal information more accessible promotes fairness and strengthens public trust in the justice system.
Professional Philosophy and Legal Values
Throughout his career, Jonathan Woolsey has demonstrated a consistent commitment to legal integrity. Whether representing insurers, advising corporations, or campaigning for judicial office, he has emphasized the importance of rules, structure, and impartiality.
His statement during the 2024 campaign, that he believes deeply in an independent judiciary that adheres strictly to the rule of law, summarizes this philosophy. For Woolsey, the legitimacy of the legal system depends on judges, attorneys, and institutions following established legal standards rather than personal or political agendas.
Current Role and Ongoing Work
Today, Jonathan Woolsey continues to practice law in Minnesota while serving as corporate counsel for InfoSync. He remains active in the legal community through his professional work and ongoing engagement with legal issues.
His career reflects the evolving nature of modern law, where attorneys often move between litigation, corporate advising, technology, and public service. Woolsey’s ability to navigate these different environments speaks to his adaptability and dedication to legal professionalism.
Why Jonathan Woolsey’s Career Matters
Jonathan Woolsey’s story is not one of celebrity or headline-making cases, but it is a meaningful example of what it means to build a responsible legal career. He represents the many attorneys who work behind the scenes to keep systems functioning, businesses compliant, and disputes resolved fairly.
His journey, from student attorney to workers’ compensation specialist, from eDiscovery manager to corporate counsel, and from private lawyer to judicial candidate, shows how law offers multiple paths for service and impact.
For aspiring attorneys, his career demonstrates the value of gaining experience across different areas of practice. For the public, it highlights the importance of lawyers who respect legal principles and work to uphold them in every role they take on.
Conclusion
Jonathan Woolsey is a Minnesota attorney whose career reflects dedication to fairness, professionalism, and the rule of law. With more than a decade of experience in workers’ compensation, litigation, corporate counsel, and legal education, he has built a reputation as a thoughtful and capable legal professional.
Although his 2024 judicial campaign did not result in election, it underscored his commitment to an independent and principled judiciary. Through his ongoing legal work and public engagement, Woolsey continues to contribute to Minnesota’s legal community in meaningful ways.
His story is a reminder that the strength of the justice system depends not only on judges and high-profile cases, but also on the many attorneys who work every day to uphold its foundations.
