Ransomware has transformed from a nuisance affecting individual PC users into the most destructive form of cybercrime, causing billions of dollars in damages annually. This 2026 retrospective traces the evolution of ransomware and examines what the future holds. The first recorded ransomware, AIDS Trojan (1989), spread via floppy disks and used simple symmetric encryption, with keys mailed on paper to the attacker. The 2010s saw the rise of CryptoLocker, which introduced Bitcoin as an untraceable payment method and sophisticated encryption that made ransom payment the only practical recovery option. The 2020s brought Ransomware-as-a-Service (RaaS), professionalizing cybercrime with dedicated affiliates, 24/7 victim support teams, and sophisticated negotiation processes. LockBit 3.0 became the most prolific RANSOMWARE variant, generating over million in payments from victims including hospitals, governments, and critical infrastructure. Double and triple extortion attacks ??threatening to release stolen data and notify customers in addition to encrypting files ??became standard practice. In 2025, AI-generated polymorphic ransomware that automatically adapts to evade detection was documented in the wild. The economics of ransomware have created a professional underground economy with specialized roles: initial access brokers, malware developers, affiliates, negotiators, and money launderers. Understanding this evolution is essential for building effective defenses against modern ransomware attacks.