Kathryn I. Osborne

Kathryn I. Osborne
Distinguished female lawyer, donned in a sleek black blazered attire, with prescise eyeglasses illuminated against a refined gray backdrop, expertly symbolizing our esteemed Law Firm situated in Hamilton, Ontario.

Kathryn I. Osborne


About Kathryn I. Osborne


Kathryn is the Managing Partner at SimpsonWigle LAW, focusing her practice on corporate commercial law and commercial real estate. Her client base is comprised of all types of enterprises, from family-owned businesses, entrepreneurs and professionals to multi-jurisdictional organizations, across many sectors.

Kathryn has extensive experience in the purchase, sale and financing of businesses and major assets, shareholders’ agreements, partnership and joint venture agreements, corporate organization matters, the preparation and review of business contracts and commercial leases, secured transactions and commercial real estate. She represents both institutional and non-institutional lenders in secured loan transactions.

Holding a designation as a Family Enterprise Advisor (FEA) she particularly enjoys working with business family clients of all sizes as corporate counsel and as an advisor to those families on ownership and governance matters, transitions, corporate organizational planning and continuity.

Skilled in working collaboratively with other key advisors to the family business, Kathryn advises and guides business owners throughout the life cycle of their business. She is able to connect them, where appropriate, with other expert resources and in times of business turmoil, Kathryn  is able to assist clients with refocus and restructuring.


“I pay attention to the details, but never lose sight of the big picture. There’s no substitute for experience and fundamentally good judgement.”


“It’s important for clients to understand the potential risks they might encounter and then make a practical  decision that’s right for that client – I’m not afraid to make recommendations and to explore options to support that decision.  My clients trust me, even when I say things they might not want to hear.”


“A good lawyer is always developing. Any time I gain some new insight that I can bring forward to the next file is satisfying. This job is fast-paced and interesting – when I can apply learning from real people and actual experiences and bring greater value to the client, that’s rewarding.”


Kathryn is Co-Managing Partner of SimpsonWigle LAW LLP. As well, she is currently on the Board of Directors of Attorneys for Family Held Enterprises (AFHE), a U.S.  based organization.

In 2018 she concluded her term as Chair on the Board of Directors for Joseph Brant Hospital in Burlington. Her commitment to the hospital was extensive, including continuing leadership roles over several years including on various committees.

In the past, Kathryn has served on various other community boards in leadership capacities.

Admissions, Education & Associations


  • Called to the Bar in Ontario, 1989


  • FAMILY ENTERPRISE ADVISOR™ Certification, 2015
  • LL.B. University of Western Ontario 1988
  • B.A. University of Western Ontario 1985


  • Law Society of Ontario
  • Hamilton Law Association
  • Ontario Bar Association
  • American Bar Association
Contemporary office setting, adorned with a sophisticated glass sculpture placed on a polished wooden cabinet and a professionally mounted photograph of Hamilton, Ontario gracing the wall.


Services Offered