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