SoftBank Bets on Bitcoin (Again): Can Masayoshi Son Rewrite His Crypto Legacy?

Japan’s Tech Powerhouse Re-Enters Crypto via Strategic Backing of Twenty One Capital

SoftBank Group, the $308.7 billion Japanese investment titan, is diving back into Bitcoin—despite its painful $130 million loss during the 2018 crypto crash. This time, however, it’s doing things differently.

In a move that could reshape institutional sentiment, SoftBank is now backing a new Bitcoin investment vehicle called Twenty One Capital, alongside crypto heavyweights Tether, Bitfinex, and Cantor Fitzgerald. With Bitcoin hovering around $93,000—a stark contrast to the ~$20,000 peak during SoftBank’s original investment—the question for investors becomes: Is this redemption or repetition?

Déjà Vu or Game Changer?

A Painful Past: SoftBank’s 2018 BTC Exit

To understand why this story matters, you have to revisit SoftBank’s infamous crypto misadventure.

In late 2017, as Bitcoin reached its then-all-time high, SoftBank founder Masayoshi Son personally invested in the asset at the peak of the ICO frenzy. But when Bitcoin started collapsing in early 2018, Son exited his position—locking in a massive $130 million loss, as reported by the Wall Street Journal.

Had Son simply held that investment, it would now be worth nearly 5x more, a stinging lesson in long-term conviction.

That past has loomed large over SoftBank’s public image in the crypto world—until now.

Why This Time Could Be Different

Institutional Infrastructure, Not FOMO

Unlike its prior speculative entry, SoftBank’s 2025 reentry is more strategic and institutional in nature. By backing Twenty One Capital with partners like Tether and Bitfinex, the firm is signaling a measured, high-conviction approach focused on infrastructure rather than price action.

In fact, Jeff Park of Bitwise argues that SoftBank’s involvement is more akin to a Japanese sovereign wealth fund engaging with Bitcoin—a significant departure from speculative plays.

This means SoftBank isn’t just buying Bitcoin. It’s backing the platforms and financial rails that support Bitcoin’s long-term adoption—placing it at the center of the next institutional wave.

The Bigger Picture: SoftBank, AI, and Market Psychology

Connecting the Dots: Oracle, AI Infrastructure, and SoftBank’s Influence

Interestingly, SoftBank’s involvement in cutting-edge technology isn’t limited to Bitcoin. It’s also participating in a $100 billion U.S. AI infrastructure initiative alongside Oracle (ORCL) and OpenAI, as announced by President Trump earlier this year.

In theory, that should have been bullish for Oracle. But ORCL stock has fallen 28% since the January announcement, while the Nasdaq dropped just 12% in the same period.

Some analysts attribute the slump to broader macro headwinds and geopolitical uncertainty. Others, like Quinn Thompson, founder of crypto hedge fund Lekker Capital, took a more humorous—and ominous—view:

“When SoftBank enters an asset you own, you sell. I don’t make the rules,” he posted on X, suggesting SoftBank’s entrance is often followed by asset underperformance.

Investor Sentiment: Fear or Opportunity?

The SoftBank Effect: Bad Luck or Self-Fulfilling Prophecy?

This brings up a key tension: Does SoftBank’s presence invite market skepticism? Or is this a rare chance to front-run long-term institutional capital?

For skeptics, SoftBank’s return to crypto may feel like a warning sign—especially for those haunted by the collapse of high-profile tech investments from the Vision Fund era. For optimists, however, this could be the early innings of SoftBank’s redemption arc in the Bitcoin narrative.

The difference this time? SoftBank is not going it alone. With support from major players in both TradFi (Cantor Fitzgerald) and crypto (Tether and Bitfinex), this is more than a solo gamble—it’s a coordinated institutional push.

CEO Playbook: What This Means for Business Leaders

1. Bitcoin Is Institutionalizing—Again

SoftBank’s strategic backing of an investment vehicle signals that Bitcoin is no longer just retail-driven. Global power players are shaping infrastructure behind the scenes.

2. Skepticism Can Be a Signal

While market jokes about the “SoftBank curse” continue, the firm’s reentry during a bullish Bitcoin cycle is notable. Smart money is often contrarian in the face of short-term fear.

3. AI and Bitcoin May Be Interlinked

With SoftBank involved in both crypto infrastructure and AI development, the convergence of these technologies should be on every executive’s radar. AI needs decentralized data. Bitcoin provides decentralized trust. Their overlap will be fertile ground for innovation.

Is SoftBank’s Bitcoin Play a Signal to Buy?

SoftBank’s history with Bitcoin is a cautionary tale—but it’s also a story of timing, conviction, and long-term potential.

This time around, Masayoshi Son and his team seem to be embracing a deeper, more systemic role in crypto’s evolution. They’re not chasing price spikes; they’re helping build the pipes and plumbing of digital finance.

If they succeed, SoftBank may go from being Bitcoin’s most famous loser to one of its most strategic champions.

And that’s a narrative the markets—and CEOs—can’t afford to ignore.

Disclaimer: The above press release has been provided by a third party. We do not verify or endorse the content and will not be responsible for any inaccuracies, claims, or damages arising from the same.