SoftBank Reinvests in Bitcoin After $130M Loss—Will This Attempt Be More Successful?

After a notable absence from the crypto market following a heavy personal loss, SoftBank is reentering the world of digital assets, this time by supporting a new bitcoin investment venture, Twenty One Capital. This latest initiative, in partnership with Tether, Bitfinex, and Cantor Fitzgerald, signals SoftBank’s renewed commitment to bitcoin, even though its founder, Masayoshi Son, faced a significant financial setback just a few years ago.

For some, SoftBank’s involvement in bitcoin again is seen as a positive shift for the cryptocurrency ecosystem. The firm, which manages over $308 billion in assets, has the potential to drive further institutional adoption of digital assets. Jeff Park, head of alpha strategies at Bitwise, likens SoftBank’s move to a major sovereign wealth fund stepping into the crypto space, providing additional legitimacy to the industry.

However, for those who remember SoftBank’s earlier foray into bitcoin, this return might stir up feelings of déjà vu rather than optimism.

Back in 2019, SoftBank’s founder, Masayoshi Son, made headlines for a disastrous personal bitcoin investment. Son jumped into the crypto market in late 2017, during the height of the ICO boom, when bitcoin’s price had skyrocketed to nearly $20,000. But by early 2018, as the market began to crash, Son sold off his holdings, incurring a loss of $130 million, as reported by the Wall Street Journal.

Given bitcoin’s current price of $93,000, Son’s original investment would have been highly profitable had he held onto it. This raises an important question for investors: could this time around be more successful for SoftBank?

To gain some insight, one could look at SoftBank’s recent involvement with AI. In January, U.S. President Donald Trump announced a major $100 billion push for AI infrastructure, with SoftBank collaborating alongside OpenAI and Oracle (ORCL). While one might expect this to boost Oracle’s stock, it has instead fallen by 28% since the announcement, while the broader Nasdaq has dropped by only 12%.

Some analysts have linked this underperformance to SoftBank’s participation in the project. “When SoftBank enters an asset you own, you sell. I don’t make the rules,” joked Quinn Thompson, founder of crypto hedge fund Lekker Capital, in a post on X.

Now, as SoftBank reenters the crypto world through Twenty One Capital, investors are left wondering whether this second attempt at bitcoin investment will result in a profitable venture or whether it will end in another missed opportunity.