In the 1988 first round playoffs, the Cleveland Cavaliers met MVP and Defensive Player of the Year Michael Jordan and the Chicago Bulls. No one expected the Cavs to push Jordan and the Bulls as hard as they did as they forced a deciding fifth game. Though the Cavs lost that fifth game, a new rivalry was born between two teams eager to be next in line as one of the best nab teams in the East.
Bolstered by their performance, the talented Cavs worked their routine for the ’89 season to attain the second best record (57–25) in the east. And with the fracturing of the talented but selfish team ethic of the Bulls, the Cavs seemed poised to avenge their rematch with Chicago in the first round. The Cavaliers swept the 1988–89 season series against the Bulls [6–0], outscoring the Bulls 635 to 561. True to form, the series went to a deciding fifth game. But with three seconds left on the clock Jordan scored one of the most famous game winning shots in basketball history. Dubbed “The Shot” by Cleveland fans, Jordan shot over the outstretched arm of Craig Ehlo to score a buzzer-beater. While the Cavs would rebuild and recover over the next three years, the Bulls would go on to championship status before their next meeting.
In 1992 the second seeded Cavs met the top seeded champion Bulls in the Eastern Finals. Though putting on another tough effort, the Bulls beat the Cavs 4–2, but not before Cavs reserve Danny Ferry attacked Michael Jordan with a flurry of seemingly unprovoked punches in one game. The Bulls went on to win their second NBA title.
The two teams met again in the 1993 semifinals but the underdog Cavs were swept by Jordan and the Bulls on the way to their third NBA teams title. Jordan’s game winning shot in Game Four only went further to prove that the Cavs seemed cursed never to defeat number 23.
With Jordan’s unexpected retirement prior to the ’94 season, the Cavs readied themselves to finally end the Chicago curse. Meeting once again in the first round play-offs, the Cavs would once again face defeat. Though Jordan was gone, Scottie Pippen would lead Chicago to a 3–0 sweep over Cleveland, and prove that it was the team, not Jordan, who beat the Cavs. The Cavs would remain an unremarkable team throughout the rest of the decade while the Bulls would go on to win three more championships.
The two teams didn’t meet each other in the playoffs until the first round of the 2010 NBA Playoffs. The Cavaliers, along with their superstar and the reigning MVP, LeBron James, were the strong top seeded, and the Bulls with their young star Derrick Rose, were the #8 seeded underdog. LeBron James took over this series, scoring 31.8 ppg in the series, and the Cavs went on to beat the Bulls for the first time in their history, 4 games to 1. But in the next round, the Cavs were eliminated by the Boston Celtics, and this Cleveland franchise remained with no titles in their case.
