The Cavaliers opened their inaugural season losing their first 15 games and struggled in their early years, placing no better than sixth in the Eastern Conference during their first five seasons. The team won their first Central Division title in 1976, which also marked the first winning season and playoff appearance in franchise history, where they advanced to the Eastern Conference Finals. The franchise was purchased by Ted Stepien in 1980. Stepien's tenure as owner was marked by six coaching changes, questionable trades and draft decisions, and poor attendance, leading to $15 million in financial losses. The Cavs went 66–180 in that time and endured a 24-game losing streak spanning the 1981–82 and 1982–83 seasons.
George and Gordon Gund purchased the franchise in 1983. During the latter half of the 1980s and through much of the 1990s, the Cavs were a regular playoff contender, led by players such as Mark Price and Brad Daugherty, and advanced to the Eastern Conference Finals in 1992. After the team's playoff appearance in 1998, however, the Cavs had six consecutive losing seasons with no playoff action.
Jewish billionaire Dan Gilbert has owned the team since March 2005.