Live and Learn: reflections on life and the law from retired Osler M&A king Clay Horner

At Osler, Hoskin & Harcourt LLP until his retirement in 2018, Clay Horner earned a reputation as a nationally and internationally recognized leading advisor for mergers and acquisitions in Canada, with extensive experience in counselling senior management and boards of directors of leading public and private corporations. He acted on many significant transactions with US and international law firms and investment banks, particularly cross border transactions. He was the lead counsel to the “Wise Persons” committee appointed to recommend the best securities regulatory system for Canada and, as a former managing partner of the New York office, worked extensively in cross-border acquisitions, divestitures and financing.

Recently, Horner has become a keen user of LinkedIn, writing posts that have attracted thousands of impressions. Topics range from the state of M&A and leadership qualities to what he’d like law students and young lawyers to know. In this recent Q&A, Horner shares some of those thoughts.

So, you officially retired from Osler in 2018 – but have you really retired? What have you been doing?

After my [skiing] accident in December 2011, I returned to the office late in Spring of 2012. I had learned to walk again and, with 750 hours of practice, could walk as far as two kilometres with someone walking close to me. In August of 2012, I had surgery to address extremely intense neural pain in my injured arm. The surgery accomplished that but drastically did further damage to my spine and, consequently, to my other leg, which had only minimal damage from the original injury. I then returned to inpatient rehabilitation for four more months. Over time, both legs have suffered further decline, and I haven’t been mobile since 2015. 

Nevertheless, I returned to lead some of the most consequential transactions of my career, including Shoppers Drug Mart-Loblaw; Tim Horton-Burger King; TPG-Fosun-Cirque du Soleil; Valeant-Pershing Square’s offer for Allergan; and the Valeant acquisition of Bausch + Lomb.

I also focused intensely on preparing my mentees to succeed me, and I am very proud of the incredible relationships I left them to carry on. That is one of the most important obligations of senior leaders, and too often, it is not discharged by insecure senior partners.

By 2017, I was satisfied that I had set a great example in client transfer, but worried about some other developments. I decided to retire in April 2018. 

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Obviously, a life of travel and golf was not an option. On that matter, I had travelled a great deal, on business and with my family, and played a lot of golf. While many long nights or weekends were spent working on finalizing transactions, the law wasn’t my life, and I rarely thought about work when I was doing something else. I think it is a matter of priorities, how you are “wired.” I’m not impressed by anyone who brags about how many hours they work. I am a quality, not quantity, person.

I was very fortunate that I had several clients who wanted me to stay involved in their most important matters and that the timing of those matters worked out. 

I advised the board of a fantastic Canadian technology company named Ethoca in a sale to Mastercard, helped the Board of a Canadian gaming company realize a very successful transition to the London Stock Exchange, was the strategic advisor to long-time clients and wonderful friends John and Benjie Levy in the sale of The Score to ESPN Bet, and worked closely with another long-time friend, Geoff Gold, the executive VP of Kinross Gold. I was honoured that these longtime friends called on me to advise them. 

More recently, this year, I was involved in resolving the Rogers family matters and advising the special committee of Argonaut Gold. I am also involved in a couple of other confidential matters.

In 2023, I had a terrific experience advising the board of Bruce Telecom on a sale to a private equity firm. I grew up in a small town and enjoyed working with directors in selling one of the last community-owned telephone companies in Canada. I felt like a small-town lawyer helping steward a company of huge regional importance into safe hands in a digital age requiring a massive investment in delivering fibre to the whole region. I am now involved in a similar situation in another part of the province that has been of great interest to me.

A special pleasure has been working with amazingly talented lawyers at firms with whom I hadn’t done much prior work. As I have written on LinkedIn, there is greatness beyond the so-called “Seven Sisters” firms, and I am most impressed by the “best values” sisters. Changes in the economy now favour firms with outstanding leadership in particular sectors, not necessarily those just covering all bases.

So, I’m retired, but I have the time and interest to read the NYT, WSJ, the Globe and Mail, the Financial Times, and four horse racing publications every day. I only take on matters with people I like or believe I will like. That allows me to work with people I haven’t worked with before, concentrate on working with the most junior people on the matter, and be very direct about where I think the whole team can do better.

You’ve become very active on LinkedIn. What about the medium do you find useful or enjoyable?

I decided late in 2023 that I needed to engage with more people than my family and closest, long-time friends. I had joined LinkedIn several years ago but hadn’t really been active.

I found that a lot of my network was active and posting with some regularity. I instantly recognized how active law students were, and that got me thinking about how I might help them. Students have always been a huge priority for me. I loved law school when I discovered how I could combine my interest in business with legal subjects, particularly the law of transactions and fiduciary duties and the substantive role of boards, and that was enhanced while doing my LLM at Harvard Law School.

My real LinkedIn “career” began with a series of posts entitled “Lessons for Lawyers Speaking to the Board of Directors.” Out of nowhere, these posts had 20,000 readers. I recommend them to students and lawyers of all ages as they represent a distillation of what I learned and got the most credit for over 30 years of working with boards. 

I progressed from that to a series of posts on firm and leader values, highlighting people I admire and recommend as examples to law students.

You mention having talked to many law students and young lawyers – what are you learning from them?

First, I have seen how wonderful and engaged they are. I have learned that they support each other; in fact, many partners could learn from them. I have learned how varied their backgrounds and interests are. They are far less rigid than my generation was.

I have encouraged them to speak up and let firms know when they would like to do something else. I recalled my experience as an articling student. Late in the articling year, I got a big assignment from a crusty senior partner in an area he knew I was not interested in. Thankfully, I had three weeks to do it. I worked hard on it and advanced very definite views about the right way to proceed. I left it on his desk the afternoon before he was to return. I didn’t hear from him for a week and was getting ready for a “bruising.” He called me the next day and said, “I know you have no interest in this or my area [of law]. This is fantastic. I wanted to hate it, but you have given this the same approach as you would have for (Osler legend) Purdy Crawford. I admire that.”

It was the most valuable experience of my articling year, and I had a great relationship with him for the remaining years of his time at the firm.

Some of your LinkedIn posts deal with how those with disabilities, or who become disabled, are treated in society. What are your thoughts on that?

Before my accident, I had no experience with people who had suffered catastrophic injuries. If I can say anything positive, it is better to retain your mental faculties if possible! Law and business are about thinking.

I don’t think some businesses understand great disabilities. Failing to return calls or emails from people with disabilities is pure discrimination. So are unilateral changes to important business terms. I was very fortunate that I already had great relationships and a deal catalogue.

There is no greater truism for the catastrophically disabled than “You learn who your friends are!” Many people “wander” away. I have ten friends who have been “pure gold.” My American and Euro firm friends have been “pure gold.” Only one of my pure gold Canadian friends is a practising lawyer (executive), and another is a former lawyer.

My family has been an unimaginable “gold standard.” In almost 13 years, at least one of our children has been at home overnight for all but 150 days.

You’re considered a mergers and acquisitions dealmaker extraordinaire – what are the qualities an M&A lawyer needs to succeed?

The essential skills of a great M&A lawyer are: 

• A love of business and being current on what is going on.
• Preparation: know the interests (as opposed to the positions) of all parties.
• Understanding the zone of reasonableness. If there are five key issues and roughly evenly placed parties, each will win one issue outright, two will get reasonably divided, and one (hopefully one that matters) will go to best advocacy.
• Deals involving families or controlled companies are not like deals between widely held companies.
• Gain the confidence of the other professionals (particularly the investment bankers) on the deal.
• Show the CEO you can solve problems that matter to that person, which may be a function of your broader relationships.
• Treat everyone well and like they matter to the deal.
• Speak up with solutions, not a legal speech or canvas of far-out options.
• Have a great junior working with you.
• Understand the culture of international parties
• Show the board you know what matters.

What are your thoughts on M&A and deal-making today, and how may they differ from when you were in the thick of things?

In Canada, we are past the golden age of big companies doing big deals regularly. We have a concentrated corporate sector in key industries, fewer companies of scale of interest to non-Canadian companies, a declining stock market and US firms taking a big share of the cross-border deals.

I had the good fortune to practise in the golden age, with deals for or opposite each of the Bronfman, Eaton, Irving, McCain, Molson, Reichman and Rogers families. 

My favourite transactions involved truly different jurisdictions. One was the first Western mining acquisition in South Africa post-apartheid, and another was the first Chinese acquisition of a Western-listed oil company.

You were chairman of Woodbine Entertainment until not so long ago, and you are known for a strong love of horses and horse racing. Where does that stand today?

I spent 18 years on the Woodbine board, with 16 of those years as vice-chair or chair. I violated every rule of board turnover!

My interest in standardbred racing came from my father, a founding member of a local businessmen’s club that built its own training centre. A great benefit was that although we lived in a small Ottawa Valley town, I spent a lot of time in Montreal during the summer racing season. My brother and I started buying better-pedigreed horses when I was a fourth-year lawyer. 

I learned a lot on the Woodbine board in terms of strategic planning, real estate development, regulatory relationships and labour relations. I also met many Canadian, US and European businesspeople. Several of them became clients. We have been fortunate to have owned five Canadian champions and seven million-dollar winners. 

In 2020, I was asked to join a group of Canadians in a thoroughbred partnership managed by Donato Lanni, a Canadian who is the most prominent bloodstock agent in the US. Lanni generally buys for the American captains of industry and has selected many Kentucky Derby winners and horses syndicated for US $20 million.

Lanni’s dream was to buy a potential Queen’s Plate [now King’s Plate] winner at a working man’s (by thoroughbred racing standards) price.

Moira is her name, and she won both the Woodbine Oaks (by eight lengths) for fillies and the last Queen’s Plate in 2022 by nine lengths in an all-time Woodbine track record time (for now).

She is racing her final year in 2024 at the age of five, with the Breeders Cup World Championship as her goal. At four, she finished third as the top North American by only a length, defeated only by two European mares owned by Middle Eastern royalty and part of the greatest Irish racing dynasty. She has been a great tonic for me. 

Final thoughts for law students entering the profession? 

Do something you love, even if it takes several changes to find it. One of the best messages I have received on LinkedIn was from someone who thanked me for giving him the most important advice of his life. He asked me if I remembered it. I replied that I didn’t. He responded that I had asked him on an elevator, “Is something wrong? You look sad.” He responded, “I don’t enjoy doing this.” I said, “Quit as soon as you can and do something else.” He did that and filled me in on a great 30-year career outside law.

Be passionate about what you do, but don’t let it be your life or your most important thing. Participate in the community; it will make you more interesting and lead you to clients. Give back.

Find a real mentor who cares for you and is truly successful. Listen to them, and don’t be shy about asking them to watch out for you and help you. As soon as you can, do that for another student or young lawyer.