Kevin O’Leary in 2026: From Crypto Deals to Political Firebrand and a $70B Alberta Bet
Kevin O’Leary, the sharp-tongued “Mr. Wonderful” from Shark Tank and Dragons’ Den, is making headlines across the board as 2026 kicks off. Far from a quiet retirement, the Canadian billionaire is actively shaping the crypto landscape, dropping blunt financial advice, and making colossal investment bets, all while remaining one of the most provocative political commentators in North America. His moves offer a real-time case study in high-stakes investing and unfiltered opinion.
Whether he’s warning homebuyers about “money traps” or announcing a data centre project worth more than the GDP of some provinces, O’Leary’s influence stretches from Main Street to Bay Street and beyond. Here’s a breakdown of what the iconic investor is up to now.
The Business Moves: Crypto, AI, and Building a Legacy
O’Leary’s portfolio is as diverse as it is ambitious. His venture firm, O’Leary Ventures, is behind some of the most talked-about deals in Canada.
WonderFi’s Regulated Crypto Play
In a landmark move for the Canadian cryptocurrency sector, WonderFi—a company backed by O’Leary—is set to purchase Bitbuy’s parent company, First Ledger. This marks the first takeover of a regulated crypto platform in the country, signaling a major consolidation and a bet on the future of compliant digital asset trading.
The $70 Billion Alberta Gambit
Perhaps the most staggering news is O’Leary’s vision for a massive technology investment in Alberta. He has announced plans to develop a $70 billion AI tech park and data centre, a project that could fundamentally transform the province’s economy and position Canada as a heavyweight in the artificial intelligence infrastructure race.
| Key O’Leary Business Ventures (Recent) | Details | Estimated Value/Scale |
|---|---|---|
| WonderFi / Bitbuy Acquisition | First regulated crypto platform takeover in Canada. | Deal value not publicly disclosed. |
| Alberta AI Tech Park & Data Centre | Proposed development to host AI infrastructure. | $70 billion (CAD) |
| Wonder Valley Fund | O’Leary Ventures’ investment arm for tech startups. | Portfolio includes AI, fintech, and renewable energy. |
O’Leary’s Unvarnished Financial Advice
Never one to mince words, O’Leary has been vocal about personal finance, specifically targeting what he sees as a critical error for Canadian homeowners.
“Mortgage payments should not be a source of constant financial stress. The biggest money trap people fall into without noticing is buying a house that’s simply too large for their needs.”
His advice is straightforward: prioritize affordability and liquidity over square footage. He argues that oversized mortgages drain capital that could be better deployed in investments, a classic O’Leary stance that prioritizes money-making assets over depreciating liabilities.
Political Commentary: A “Brutal” Critique of the Election
Following the 2024 U.S. election, O’Leary emerged as a fierce supporter of Donald Trump’s economic policies and an equally fierce critic of the Democratic campaign. His appearances on CNN and other networks were marked by characteristically blunt assessments.
He labeled Vice President Kamala Harris a “broken candidate with no compassion” and a “loser” who was “slaughtered” in the election, comments that sparked intense debate and highlighted his role as a conservative business voice in media. He has consistently framed the Trump economic approach as more favourable for investors and growth.
From TV to the Silver Screen
Adding a dash of Hollywood to his resume, O’Leary recently discussed landing a cameo role as a wealthy businessman in the film Marty Supreme. He recounted getting the call while relaxing at his lake house, proving that even for a billionaire, the chance to play one on the big screen is still a thrill.
The Foundation of the Fortune
For those wondering how O’Leary bankrolls his opinions and investments, his wealth was built on a few legendary deals. The cornerstone was the sale of his software company, SoftKey, to Mattel in 1999 for approximately $3.8 billion. This table breaks down the man behind the money.
| Biography at a Glance: Kevin O’Leary | |
|---|---|
| Full Name | Kevin O’Leary |
| Known For | Shark Tank (U.S.), Dragons’ Den (Canada), Investor, Entrepreneur |
| Key Wealth Event | Sale of SoftKey to Mattel (1999) for ~$3.8 billion (USD) |
| Recent Major Project | Proposed $70B AI Tech Park in Alberta |
| Public Persona | Direct, contrarian, pro-business political commentator |
As 2026 unfolds, Kevin O’Leary remains a multifaceted force. He is simultaneously a deal-maker pushing the boundaries of crypto and AI, a personal finance pundit warning against debt, and a political lightning rod. For investors and observers alike, his next move is always worth watching.
Frequently Asked Questions
What is Kevin O’Leary’s biggest investment in 2026?
His most ambitious announced project is a proposed $70 billion (CAD) AI tech park and data centre development in Alberta. This represents one of the largest private investment proposals in Canadian history.
What did Kevin O’Leary say about buying a house?
O’Leary has strongly warned against buying a house that is too large, calling it the “biggest money trap.” He advises that mortgage payments should not cause financial stress and that excess capital should be directed into income-generating investments instead.
Why was Kevin O’Leary in the news after the U.S. election?
He made headlines for his blunt political commentary, fully endorsing Donald Trump’s economic policies and offering a harsh critique of Kamala Harris’s campaign, which he described as a failure and labeled her a “broken candidate.”
How did Kevin O’Leary make his original fortune?
His wealth was cemented by the sale of his educational software company, SoftKey International, to toy giant Mattel in 1999 for approximately $3.8 billion (USD). This deal transformed him into a multi-millionaire and provided the capital for his future ventures.