Rob Lilly is widely known and respected by other lawyers for his confidence and tenacity in everything he does. “Tireless”, “whip-smart” and “compassionate” are how clients describe him. Whether negotiating a large long-term disability settlement or helping an executive get a bonus wrongfully withheld, Rob will not let up until justice is served.  He also genuinely cares about his clients.  Read Rob’s reviews.

Rob is Levitt LLP’s long-term disability law specialist.  He has recovered millions in long-term disability settlements for his clients.  He also practices in employment law, personal injury and commercial litigation. Rob also writes columns for the National Post on employment law and long-term disability topics.

He has appeared before all levels of court in Ontario including the Ontario Superior Court of Justice, Divisional Court of Justice and Court of Appeal along with various administrative tribunals.  Read Rob’s recent cases.

Prior to joining Levitt LLP, Rob was a named partner at a disability and employment law firm for nearly five years.  Before that, Rob worked at a boutique employment and labour law firm and also for the largest insurance defence firm in Canada, where he learned the inner-workings of insurance companies and their weaknesses.

Rob received his law degree from the University of Victoria, where he developed his love for hiking and nature.


  • Employment Law
    • Wrongful and Constructive Dismissal
    • Severance Package Review
    • Employment Agreement Review
    • Non-Competition and Non-Solicitation
    • Workplace Investigations
    • Absenteeism, Disability Leaves and Leave Management
    • Human Resources Policies
    • Discipline and Termination
    • Occupational Health & Safety
    • Human Rights and Duty to Accommodate
    • Discrimination, Harassment & Sexual Harassment
  • Disability Insurance Law
    • Long-Term Disability (LTD) Appeals and Claims
    • Short-Term Disability (STD) Appeals and Claims
    • Critical Illness and Accidental Death & Dismemberment (ADD) Insurance
    • Independent Medical Examination Advice
    • Life Insurance
  • Commercial Litigation and Shareholder Disputes
  • Insurance Defence and Insurance Coverage Litigation
  • Personal Injury


  • Called to the Ontario Bar, 2010
  • Called to the British Columbia Bar, 2008
  • J.D., LL.B., University of Victoria, 2007
  • Hons. B.A, University of Victoria, 2004

Recent Decisions

  • In Gee v. Corus Entertainment Inc., 2023 CIRB 1090, Rob Lilly convinced the Canadian Industrial Relations Board to dismiss an unjust dismissal complaint on the basis that the complainant was an independent contractor, who was not entitled to the same protection as an employee under the Canada Labour Code.
  • After a 14 day reprisal hearing spanning over 1.5 years, Rob Lilly successfully argued for the dismissal of the application against our client.  In Lesa Bowen v Moore Packaging Corporation, 2022 CanLII 120951, the Ontario Labour Relations Board noted the Applicant was not credible on cross-examination and was terminated because of her escalating threats, not for any reason contrary to the Employment Standards Act.
  • In Ruel v. Air Canada, 2022 ONSC 1779, Rob Lilly secured his client the upper limit of common law damages (i.e.: 24 months of full salary, benefits, bonuses, stock options and pension), plus $65,000.00 for retiree health benefits and reinstatement into Air Canada’s flight pass program (which our expert valued at over $1.8M).  Mr. Ruel was awarded over $550,000 – which was about four times the amount Air Canada argued he should receive – plus bonuses, interest, costs and free flights for life or until the program ends.
  • In Lesa Bowen v Moore Packaging Corporation, 2021 CanLII 47575 (ON LRB), the Ontario Labour Relations Board granted Rob’s motion to dismiss the application against all four employees named personally in the application.
  • In Stahl v. 30 Forensic Engineering Inc., 2018 ONSC 1092, Rob Lilly successfully defeated the Defendant’s position that the Plaintiff was not entitled to his bonus because he was not “actively employed.” In doing so, Rob ably convinced the court to award his client $110,577 in a discretionary bonus and unpaid wages.
  • In Fermin v Intact Financial, 2016 ONSC 5631, Rob pushed back against “big insurance” and was able to get our client, a long-serving claims representative, 16 months of pay and benefits.
  • Jacobson v. Atlas Copco Canada Inc., 2015 ONSC 4, in which the employer tried to claim privilege over a human resources document which was effectively the smoking gun it did not want the plaintiff to see. Rob convinced the court that document must be disclosed to his client. Shortly thereafter, the defendant settled with his client.
  • Cilic v. Vivace Tavern Inc., 2015 ONSC 6169, in which after defeating the plaintiff’s summary judgment motion, Rob successfully opposed the plaintiff’s motion for leave to appeal to the Divisional Court of Ontario.
  • Faklan v. Niewiadomski, 2014 ONCA 697, in which Rob successfully opposed the plaintiffs’ motion to set aside an administrative dismissal order and the subsequent appeal to the Ontario Court of Appeal. In doing so, he had the claim for hundreds of thousands of dollars dismissed and recovered costs for his clients.

Read Reviews

Toronto, ON, 55-years-old, Operations Manager

“I am so thankful Rob for all you’ve done for me. From the first time I spoke with you I knew I could trust you. You listened so patiently to my situation; and made me feel important.

It was very stressful for me when my LTD got cancelled. I was so worried I would have to return to work. I was employed for 21 years with the same Company, 5 of which I had to be on LTD for severe neck and back pain, along with anxiety and panic attacks. After speaking to Rob about my LTD cancellation he explained the options for my claim. Rob, your knowledge and understanding of my claim made it easy for me to focus on my health. I appreciate you were always available to talk to me even after office hours.

I cannot begin to tell you the how much I appreciate all you’ve done for me, I have a better future because of you. Getting my settlement changed my life.I would say you are The Best. You’re confident in your ability to get the best for your clients.
Thank you, you changed my life.”

Guelph, ON, 58-years-old, Chief Executive Officer

“I was referred to Rob Lilly by a common friend.  I never met him, yet there was an immediate excellent work relationship.  Rob prudently but also forcefully and productively assisted me in a complex termination battle as former (Canadian based) CEO of an international professional organization. He managed superbly the legal AND the cultural complexities of my case, which also required affirming proper jurisdiction: an US incorporated entity, with a president from Argentina, a past president from South Africa and an ExCo roster which included a German, an American and an Indian.  Multicultural for sure.

Rob supported me working in perfect partnership, I found him fully reliable and trustworthy!  His legal expertise and strategic mind were superb.  Fast and considerate.  A fair person.

Long story short, the US lawyer folded quickly.  The more militant members of ExCo try to drag the process causing delays but eventually folded as well.  Their cultural diversity had (were advised by their lawyer ) to defer to Canadian law, a point masterfully argued by Rob!  The final transaction was financially very satisfactory.

Can only say: THANK YOU Rob!  Highly recommended!”

Bradford, ON, 45-years-old, Program Administrator

“I wanted to Thank You for all of help, support and professionalism with my case. I never thought in a million years I would of been going through this situation but sometimes in life there is no exceptions, but I am glad that I had the best person and team alongside during this transition. I will gladly recommend your services to anyone that may ever need it. Thank you again for your help.”