Newly released documents reveal a long-running and close relationship between convicted sex offender Jeffrey Epstein and crypto entrepreneur Brock Pierce, dating from 2011 until shortly before Epstein’s 2019 death. Pierce and Epstein frequently discussed business, especially cryptocurrency investments and networking, as well as women in a transactional manner. Epstein invested in crypto companies—including Blockstream and Coinbase—sometimes through or alongside Pierce. Their communications also referenced “Alice,” a woman who had declined Pierce’s marriage proposal but remained connected to both men. Epstein, who sometimes referred to Alice as his assistant or Pierce’s “little girlfriend,” maintained regular contact with her, offering personal advice and assistance, while also discussing her with Pierce. The documents show Epstein using his influence to connect Pierce with powerful figures, and vice versa; they also raised concerns about improper redactions that exposed the identities of possible victims. Pierce’s representation of his association with Epstein—posthumously described as minimal and professional—contradicts the evidence of personal and ongoing email exchanges. The documents provide new insight into how Epstein cultivated influential contacts within the crypto world after his 2008 conviction.