The response to my exploration of a return of MLB to Montreal has been extremely positive. For anyone trying to understand where sports ownership is going — whether as a civic leader, entrepreneur, fan, or investor — you really need to look at the last 30 years through a very simple lens:

Era 1: The Founder / Solo-Led Era (1990–2010)

Era 2: The Institutional Capital Era (2010–Present)

These two chapters tell us everything about how we got to today’s world of billion-dollar valuations, multi-sport platforms, and sovereign wealth/P.E. funds owning pieces of the global sports economy.

And they tell us a lot about where the next chapter is heading.

Era 1 — The Founder / Solo-Led Era

(Vision-driven individuals buying iconic teams for $100–300M and riding them to multi-billion-dollar valuations)

This was the era of “one person buys a team and holds it for life.”
The multiples these owners generated — mostly unintentionally — are staggering.

Here are five of the clearest examples.

1. Jerry Jones — Dallas Cowboys (NFL)

  • Bought: 1989 for $140M
  • Current value: ~$12.8B (2025 estimates)
  • Multiple: ~90X over 36 years

Why it matters:
Jones is the archetype: one owner, one vision, one of the greatest financial returns in sports history.

2. Robert Kraft — New England Patriots (NFL)

  • Bought: 1994 for $172M
  • 2025 transaction: sold 8% stake at a $9B valuation
  • Multiple: ~52X over ~30 years

Why it matters:
Classic founder-owner who later brings in institutional capital (Sixth Street) without ceding his legacy position.
A perfect hybrid for today’s world.

3. Mark Cuban — Dallas Mavericks (NBA)

  • Bought: 2000 for $285M
  • Sold majority: 2023 at a $3.5B valuation
  • Multiple: ~12X over 23 years

Why it matters:
Cuban represents tech wealth entering sports before it was cool — modernizing brands and eventually partnering with real estate capital.

4. Wyc Grousbeck — Boston Celtics (NBA)

  • Bought: 2002 for $360M
  • Sold majority: 2025 for $6.1B
  • Multiple: ~17X over 23 years

Why it matters:
Proof that patient, financially disciplined ownership can deliver venture-like outcomes in legacy sports.

5. Malcolm Glazer — Manchester United (Premier League)

  • Bought: 2005 for ~£800M (leveraged buyout)
  • Partial sale (2024–25): ~27% at ~$5–6B valuation

Why it matters:
One of the earliest examples of modern capital structure applied to sports — LBO mechanics before PE formally took over the category.

The Big Picture of Era 1

This era produced legendary multiples because timing + scarcity + media-rights expansion worked in favor of individuals who bet early.

But that era is gone.

Teams are now worth $2B–$8B+.
A solo operator rarely writes that check today.

Which leads to…

Era 2 — The Institutional Capital Era (2010–Present)

(Sports as a formal asset class: yield-focused, risk-managed, platform-driven)

As valuations exploded, the sports world entered a new phase:

  • Private equity approval in multiple leagues
  • Family offices partnering with operators
  • Data-driven optimization of stadium assets
  • Multi-team portfolios
  • Cross-border ownership
  • Media/IP arbitrage

Here are five clean examples illustrating the shift.

1. RedBird Capital — AC Milan (Serie A)

  • Bought: 2022 for €1.2B
  • Structure: RedBird control + Yankee Global Enterprises minority

Why it matters:
A PE firm running a top global football club with a platform mindset — stadium, content, commercial optimization, global brand scale.

2. Clearlake / Todd Boehly — Chelsea FC (Premier League)

  • Bought: 2022, £4.25B package (~$5.2B)
  • PE stake: Clearlake holds ~60%

Why it matters:
The largest PE-powered club acquisition to date.
Textbook consortium governance.

3. CVC Capital Partners — LaLiga Commercial Rights

  • Deal: 8.2% for €1.9–2.0B (2021)

Why it matters:
PE is no longer buying teams — it’s buying leagues and media rights ecosystems.

This is sports-as-IP-business, not sports-as-entertainment.

4. Arctos Sports Partners — Golden State Warriors (NBA)

  • Bought: 5% at ~$5.5B valuation (2021)

Why it matters:
Arctos pioneered “minority stake aggregation,” creating diversification across franchises while teams retain control.

5. Sixth Street — San Antonio Spurs (NBA)

  • Bought: 20% stake at ~$1.8B valuation (2021)

Bonus:

  • Sixth Street later invested in the Patriots (3% at $9B valuation).

Why it matters:
Sixth Street is the clearest example of PE entering legacy leagues that once prohibited institutional capital entirely.

So What Does This Mean for Montreal — or Any New Franchise Story?

The ownership landscape has evolved into two clear historical eras, but we are now entering a third:

Era 3: The Hybrid Operator Era

(Founder energy + PE discipline + multi-platform media + civic narrative)

This is the model where:

  • A mission-driven operator leads the vision (your equivalent of a Jones/Kraft/Grousbeck/Cuban-era “architect”)
  • PE provides institutional ballast
  • Family office/HNWI provides continuity + prestige
  • Media assets provide narrative power and global reach
  • City + league alignment provide legitimacy
  • Digital fanbases create momentum before shovels hit ground

This is where your story — the Peanut Project / Expos Return — fits.

You’re not trying to be Jerry Jones in 1989.
You’re trying to be:

  • The operator
  • With PE backing (minority)
  • With one HNWI or family office (prestige anchor)
  • With governance discipline
  • With a media engine no owner in history has ever had

In other words:

The first digitally-native sports ownership model.

A model that MLB, MLS, NHL, and other leagues will increasingly find attractive because:

  • It is financially stable
  • Culturally modern
  • Narrative-powered
  • Risk-managed
  • Less ego-driven
  • More institutionally compatible