Who knew that in my efforts to bring MLB & the Montreal Expos back to the city, I would be volunteering as Montréal Tourism & the Commerce Chamber’s intern/marketing assistant!

My quest to present a compelling and viable proposal to MLB when it opens up its next expansion process starts with a baseball-first, community-driven, optimal ownership structure that reflects the era of sports ownership that we are in, with not just a proper financial model but also a roadmap to build something more substantive. As I grow more confident that capital is not the constraint & continue exploratory discussions with PE firms, I recognize that for the math to work out, we need one anchor HNWI and/or Family Office. Even if there are a couple of people locally who can write such a check, realities of liquidity, time horizons means that if local groups do not emerge, I would look at my global network of investors, entrepreneurs, celebrities, family offices and so on.

To succeed in business, one must master humanities, and in this context it means putting yourself in people’s shoes. Aside from the economic allure (rare asset offering investors a safety net, historical 13% CAGR over 60 years) & the 4C (foresee) civic development project which represents the largest since Expo 67, you have to sell Montreal. I asked my digital aide Chassie to help me crystallize its selling points to answer the question: Why Montréal? Take it away Chassie:

Here’s how a serious family office would want that question answered — elevated, disciplined, and compelling — while still leaving room for the human pull of Montreal. Think of this as the answer you’d give once, knowing it will be repeated internally many times after you leave the room.

“Why Montréal?” — The Family Office Case

1. A City That Retains Families, Not Just Capital

Montreal is one of the rare North American cities where multi-generational families actually want to live.

  • World-class education (McGill, JMSB/Concordia, Université de Montréal)
  • Safe, walkable neighborhoods
  • Cultural literacy (arts, languages, history)
  • A city that raises globally fluent children without the pressure-cooker pathology of New York or London

For a family office, this isn’t lifestyle fluff — it’s succession planning.

2. Bilingual by Default, Global by Design

Montreal produces people who are:

  • fluent in English and French,
  • culturally European and North American,
  • comfortable operating across borders.

That matters to families with:

  • international holdings,
  • European ties,
  • or children who will inherit global responsibility, not just assets.

Montreal trains global citizens, not provincial heirs.

3. Geographic Sweet Spot (Time-Zone Arbitrage)

Montreal is uniquely positioned:

  • 1 hour from Toronto and New York
  • 3 hours from Chicago and Miami
  • 6 hours from Los Angeles and London

That makes it:

  • accessible to North American business,
  • viable for Europe,
  • without being swallowed by either.

It’s a city where you can do serious business without living inside a permanent emergency.

4. Low Crime, Strong Institutions, Rule of Law

This matters enormously to family offices — even when they don’t say it out loud.

  • Predictable legal system
  • Stable political environment (relative to global peers)
  • Strong healthcare
  • Low violent crime
  • No “security theater” lifestyle

Montreal offers institutional calm, which is increasingly rare.

5. Cultural Density Without Cultural Exhaustion

Montreal punches absurdly above its weight:

  • Just for Laughs
  • Osheaga
  • Jazz Festival
  • F1 Grand Prix
  • Film, food, fashion, design

But unlike global megacities:

  • culture is participatory, not performative,
  • you can actually belong instead of spectate.

This matters to families who value identity, not just access.

6. Sports as Civic Religion (The Canadiens Effect)

The Montreal Canadiens are not a team — they are institutional memory.

That translates to:

  • deep-rooted fan loyalty,
  • intergenerational attachment,
  • symbolic permanence.

For a family office thinking long-term, that kind of cultural embed is not replaceable by markets with transient fandom.

7. An Undervalued Global City (The Real Investment Thesis)

Montreal is:

  • globally recognizable,
  • culturally prestigious,
  • structurally undervalued.

That creates asymmetric upside:

  • reputational,
  • civic,
  • financial.

Families that think in decades understand the power of backing inevitability before it is priced in.

8. Quality of Life That Doesn’t Corrode Judgment

Let’s say the quiet part, tastefully.

  • The food is elite.
  • The social scene is vibrant.
  • The people are attractive — intellectually, culturally, aesthetically.

Cities that are too austere lose soul.
Cities that are too decadent lose discipline.

Montreal balances pleasure and order, which is rare — and sustainable.

The Line That Lands (Use This Sparingly)

“Montréal is one of the last cities where global capital can live a human life.”

That sentence sticks.

How a Family Office Internal Memo Would Summarize It

“Montréal offers cultural permanence, geographic efficiency, institutional stability, and generational livability — without the excess volatility or exhaustion of global megacities.”