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The following year, Ditka's coaching career hit its pinnacle on January 26, 1986, with a 46–10 win over the New England Patriots in Super Bowl XX at the Louisiana Superdome in New Orleans, Louisiana.

Ditka has stated that one of his biggest regrets in life was not letting Walter Payton score a touchdown in the Super Bowl, instead opting for Jim Mc Mahon to run it in twice and rookie defensive tackle William "The Refrigerator" Perry to run it in once.

He was an NFL champion with the 1963 Bears, and is a three-time Super Bowl champion, playing on the Cowboys Super Bowl VI team as well as winning as an assistant coach for the Cowboys in Super Bowl XII, and coaching the Bears to victory in Super Bowl XX.

He was named to both the NFL's 50th and 75th Anniversary All-Time Team.

He is the only Head Coach in the history of the Super Bowl to score a touchdown in a Super Bowl as a player.In the letter Ditka said that he would like to come back to Chicago and be the head coach of the Bears "when he was ready".Meanwhile, the Cowboys continued to win games although they did not win another Super Bowl while Ditka was there.In his first season, Ditka had 58 receptions, introducing a new dimension to a tight end position that had previously been dedicated to blocking.He also scored 12 receiving touchdowns, which was the most by a Bears rookie. He continued to play for the Bears for the next five years, earning a Pro Bowl trip each season. Many of the players from that team, including Ditka, were drafted by assistant coach George Allen, a future Hall of Famer, who was then in charge of the Bears drafts.It was masterminded by defensive coordinator Buddy Ryan, with little oversight from Ditka; in fact, Ditka and Ryan had a largely adversarial relationship dating back to Ditka's hire as Ryan, who was already on the coaching staff when Ditka joined the Bears, felt that he should have been promoted into the head coaching position.

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