If you strip away the emotion, nostalgia and spectacle of sports, what remains is the rarest asset class in modern capitalism.
There are only 30 MLB teams on Earth.
You cannot manufacture more supply.
But demand keeps rising, especially as franchises have generated roughly 13% annualized returns over the last 60 years. That track record rivals or exceeds top-tier private equity performance.
In that context, match-making becomes the most important part of any ownership bid.
Not spreadsheets.
Not logos.
Not slogans.
Matching the right partner to the right project, and managing rights, vetoes, expectations and time horizons, is the whole game.
And if Montreal is going to return to Major League Baseball, we must get the match-making and packaging right.
Why Not Every Billionaire Is a Fit (and Why Fit Matters More Than Net Worth)
One of the odd ironies of sports is the assumption that wealth alone makes someone a viable owner. It does not.
Owners must align with:
• League governance norms
• Multi-decade time horizons
• Structured veto rights
• Private equity as a co-equal partner
• The civic responsibilities unique to their market
In Montreal’s case, there is an additional dimension. Our city responds to civic-minded builders. Montreal has never been impressed by arrogance or absentee capital. It responds to people who engage with the city and understand its culture.
The founders of Montreal’s great business dynasties were not establishment figures when they began. Sam Bronfman, Pierre Peladeau and John Molson were entrepreneurs who built the families and institutions we admire today.
If I appear bold in this journey, it is only because I am acting in the same civic spirit that built modern Montreal. If I absolve them of the community’s unrealistic expectations to act as white knight and saviour, it is because I understand finance & am an empathetic person.
The HNWI and Family Office Quadrant Map
Below is a simple matrix outlining possible profiles of high net worth individuals and family offices who could, in theory, align with a modern sports ownership model. Some of these are just examples and not a fit; while other more obvious fits I envision are omitted (because while I am transparent, I am not stupid).
This is an intellectual exercise, not an outreach list. It illustrates the complexity of structuring a 21st century ownership group.
Quadrant 1: Prestige and Legacy Ownership
Motivated by symbolism, influence and platform value: Jeff Bezos, Vince McMahon, Tom Brady, Jeffrey Katzenberg etc.
Quadrant 2: Emotional Baseball Fit
These individuals love the game or love the narrative around it (and may appear in other quadrants) Tom Brady (drafted once by Expos), the Bronfman family, etc.
Quadrant 3: Montreal and Canada Connection
These individuals understand Montreal or have meaningful ties to Canada: Alain Bouchard, Stephen Bronfman…
These are not just investors, they would be stewards – whether they have the capacity and temperament, or not.
Quadrant 4: Financial Diversification and Asset-Class Exposure
These investors view sports as an inflation hedge, a scarcity asset, a platform play and a hedge against media fragmentation: Jeff Bezos, Sergey Brin, Larry Page, Alain Bouchard, etc. But even if you check off all boxes, it’s still a tall ask to expect one person to write a multi billion dollar check, which is why PE has entered the chat and the funding model I outlined per transaction and roadmap to build a global holding company of sports & entertainment assets signals the future.
It is not just “rich families.” It is a coordinated ecosystem:
• A few multigenerational business families (Bronfman, Molson, Desmarais)
• A handful of billionaire entrepreneurs (Couche Tard’s Bouchard, CGI’s Serge Godin)
• Quebec Inc.-aligned financial institutions (CDPQ, Desjardins, National Bank)
• Political insiders (past ministers, chiefs of staff, city hall operators)
• Cultural stewards (Cirque du Soleil alumni, Juste Pour Rire, Evenko)
• Old-guard CEOs (retired and current)
• Media owners
• Law firms (the gatekeepers of legitimacy)
Montreal’s establishment is smaller, tighter, more relational, and more cautious than London, New York, LA, or Toronto. But, I empathize with each person/group, and recognize each one’s personal (what drives them) and professional (is it legacy? capital preservation, growth of net worth, etc) needs and wants. They are, after all, humans like you and I.
Why “Wealthy” Doesn’t Always Mean “Available or Interested”
- Many of these individuals/families — especially legacy names like Bronfman or Molson — may have diversified portfolios, philanthropic commitments, or legacy constraints. That means liquidity, willingness to invest, and strategic interest can vary widely.
- “Rich” doesn’t equal “risk taker.” Someone deciding to back a sports/entertainment project like your Expos bid or “Willpower: Mojo Risin” concept (a Moneyball/Field of Dreams adaptation) would need not just capital, but alignment in vision, appetite for media/entertainment, and a sense of legacy or personal connection (to Montreal, legacy teams, or storytelling).
- Public net-worth estimates fluctuate with markets, currency changes, private holdings, etc. Use publicly available numbers as rough signals — not guarantees.
Why the Identity of the Anchor Matters More Than the Check Size
Private equity will fill roughly 15 to 30% of the cap table. That part is straightforward.
The anchor investor is different.
Private equity firms have defined hold periods, governance preferences, fiduciary requirements and predictable exit strategies.
Family offices do not. Their decisions are philosophical, emotional and reputational as much as financial.
That is why choosing the right anchor matters.
You are not matching a wallet to a project. You are matching values, temperament, time horizons, governance discipline, civic alignment and narrative fit.
The perfect partner is not the richest one. It is the one whose worldview matches the responsibilities of owning a franchise and the responsibilities of being a Montreal steward. In fact:
The Key: Rights, Vetoes and Alignment
Every serious investor will ask:
What are my rights
What are my vetoes
How do decisions get made
Who has operational control
What happens in deadlock
What is the exit pathway
This is normal.
I have spent 20 years building WatchMojo with zero drama, strong governance, disciplined operations, risk management and diplomatic leadership. Notably, doing our 2020 recapitalization and bringing on a PE firm taught me a ton in managing that process, and then ensuring investors were satisfied and assured post-close. That track record exists for a reason.
People will offer talking points.
I know what to expect.
I know how to respond professionally and respectfully. And, how I am going about it remains less brash than what Montreal’s builders did when they were building their alcohol, media or financial empires.
This is a marathon, not a press conference.
If I Remain Patient, This Is All Achievable
MLB controls outcomes.
I control inputs.
And Montreal controls the heart.
Everything else comes down to sequencing, governance, fit and patience.
The team is the spark.
The 4C district is the engine.
And the right anchor investor will turn both into a generational project for Quebec and Canada.
This is match-making.
This is packaging.
It requires sequencing.
This is the real work. And, thankfully for Montreal (and hopefully MLB, but other leagues if not), in the spirit of Liam Neeson’s famous monologue from Taken, while I don’t have billions or know any MLB executives/owners personally, I do have “a very particular set of skills… skills acquired over a very long career… skills that make me uniquely suited for certain mandates.”
Game on.
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