SoftBank, the Japanese investment giant with $308.7 billion in assets under management, has re-entered the world of cryptocurrency by supporting a new bitcoin investment vehicle called Twenty One Capital. This venture includes partnerships with Tether, Bitfinex, and Cantor Fitzgerald, marking another step towards institutional adoption of crypto assets. Some experts see SoftBank as similar to a Japanese sovereign wealth fund, showcasing the growing interest from traditional financial institutions in the crypto space.

On the other hand, this move may feel like déjà-vu for some as SoftBank founder Masayoshi Son previously incurred a significant loss from a personal bitcoin investment back in 2019. Despite the potential profits he could have made if he had held onto his bitcoin investment until now, he sold in early 2018, resulting in a reported $130 million loss.

Given this history, the question arises whether history will repeat itself or if things will turn out differently this time. In a recent development, SoftBank, OpenAI, and Oracle announced a $100 billion initiative to build AI infrastructure in the U.S., which initially led to a positive outlook for Oracle (ORCL) stock. However, since the announcement, ORCL stock has dropped by 28%, compared to the overall 12% decline in the Nasdaq during the same period.

While various factors contribute to this market underperformance, some analysts have linked Oracle’s selloff to SoftBank’s involvement in the AI infrastructure project. According to Quinn Thompson, founder of crypto hedge fund Lekker Capital, investors tend to sell when SoftBank enters an asset they own. The correlation between SoftBank’s participation and the decline in ORCL stock highlights the complex and interconnected nature of financial markets.

In conclusion, while SoftBank’s foray back into the crypto world with Twenty One Capital is a notable development, past experiences and possible market correlations suggest a cautious approach may be warranted.