Druckenmiller Invests $146 Million in DocuSign Flutter Entertainment

Billionaire Stanley Druckenmiller has made significant investments in two key assets, according to recent filings with the U.S. Securities and Exchange Commission. As of the first quarter of 2025, Druckenmiller allocated approximately $146 million to DocuSign and Flutter Entertainment through his Duquesne Family Office.

Druckenmiller's investment in DocuSign involved the purchase of 1.07 million shares. DocuSign is a digital platform that facilitates the electronic signing, sending, and management of documents, thereby streamlining workflows and reducing reliance on paper-based processes. This investment appears to be a strategic move to capitalize on a dip in the stock price, which fell from a high of $97.70 in January to a low of $74.70 in March. At the time of publishing, the stock was trading at $76.47.

In addition to DocuSign, Druckenmiller dramatically increased his firm’s stake in Flutter Entertainment. The investment included the acquisition of 351,200 shares valued at $72.225 million, along with call options worth $8.203 million, totaling an allocation of $80.428 million. Flutter Entertainment is a global sports betting and gaming company, operating popular brands such as FanDuel, Paddy Power, and Betfair, which offer online and retail betting services across multiple markets. This investment also seems to be a response to a pullback in Flutter’s stock, which fell from a high of $240.60 in February to a low of $194.50 in March. At the time of publishing, the stock was trading at $278.68.

Druckenmiller's investments in these two assets reflect his confidence in the digital transformation and global gaming sectors. DocuSign's platform aligns with the growing trend of digitalization, while Flutter Entertainment's diverse portfolio of gaming and betting services positions it well in the expanding global gaming market. These strategic moves underscore Druckenmiller's belief in the long-term potential of these industries, despite short-term market fluctuations.