Bobby Orr's arrival in Chicago in June 1976 was met with considerable excitement, as the Blackhawks signed the legendary defenseman to a lucrative five-year, $3 million contract. At the time, this was an enormous contract that staggered the sports world. Chicago President Bill Wirtz publicly stated his determination to sign Orr, emphasizing the gamble the team was willing to take on such a talented player. “We have gambled,” said Wirtz. “We have placed our bet down, but at least we have gambled on a thoroughbred."

Orr's career with the Boston Bruins had been nothing short of spectacular. From the 1967-68 season to the 1974-75 season, he secured the James Norris Trophy eight times, the Hart Trophy three times, the Art Ross Trophy twice, and led the Bruins to two Stanley Cups, earning the Conn Smythe Trophy twice. His speed, scoring ability, and play-making skills revolutionized the defenseman position. He holds the record for most points and assists in a single season by a defenseman. Over ten seasons with the Bruins, Orr helped the team to the playoffs eight times.

However, by the time he joined the Blackhawks, Orr's left knee was severely damaged. He had already played only ten games in his final season with the Bruins. Despite the optimism surrounding his arrival in Chicago, the Blackhawks were aware of the risks involved.

Before his first season with the Blackhawks, Orr played for Team Canada in the 1976 Canada Cup tournament, where he was voted the tournament's most valuable player.

Unfortunately, Orr's time with the Blackhawks was brief and largely marred by injury. In his first season (1976-77), he managed to play only 20 games. He sat out the entire 1977-78 season, attempting to rehabilitate his injured knee. Orr attempted a comeback in the 1978-79 season, but he played only six games before retiring at age 30. In total, Orr played just 26 games for the Blackhawks over three years, scoring six goals and 27 points.

During his time with the Blackhawks, Orr also briefly served as a co-coach alongside Bill White and Stan Mikita after the dismissal of coach Billy Reay.

Orr's final NHL goal was scored against Detroit in October 1978. He retired with 270 goals and 645 assists for 915 points in 657 games. At the time of his retirement, he was the leading defenseman in league history in goals, assists, and points.

The Hockey Hall of Fame waived its usual protocol and inducted Orr in 1979, making him the youngest living member at the time. In 2017, Orr was named one of the "100 Greatest NHL Players" in history by the National Hockey League.

Although his time with the Blackhawks was short, Bobby Orr's impact on hockey remains undeniable. His Blackhawks career is often considered a footnote to his illustrious career.