Ditka, Flores, Gary Kubiak, and Doug Pederson are also the only people in modern NFL history to win a championship as head coach of a team for which they played previously.

During the season, against the Los Angeles Rams, Ditka tied Harlon Hill's franchise record for the most receiving touchdowns in a game with four.

Ditka was also noted for decking football fan Felix Carbajal, who had run onto the playing field late in a Week 2 31–17 loss to the Rams at the Los Angeles Memorial Coliseum on September 16.

[16][17][18] On April 26, 1967, Ditka was traded to the Philadelphia Eagles along with a 1968 fourth-round pick (#106-Alan Bush), in exchange for quarterback Jack Concannon.

The transaction was intended to fill roster vacancies created by the retirements of Eagles' tight end Pete Retzlaff and Bears' quarterback Rudy Bukich.

[20] His time as a Bears player bitterly came to an end with a parting shot in which he stated that Halas "threw nickels around like manhole covers.

The Cowboys reached their first Super Bowl, losing 13–16 against the Baltimore Colts, by way of a field goal scored with five seconds left in regulation time.

He started all 14 games, posting 17 receptions for 198 yards and one touchdown, while alternating in some passing situations with rookie Jean Fugett.

In 1988,[24] his blocking and 427 career receptions for 5,812 yards and 43 touchdowns earned him the honor of being the first tight end inducted into the Pro Football Hall of Fame.

During his tenure, the Cowboys made the playoffs eight times, won six division titles, three NFC championships, and a Super Bowl victory in 1977.

In the meeting, he warned that the team would experience some turnover, but if they were all willing to work hard for him and stand with him, Ditka promised a trip to the Super Bowl within three seasons.

The following year in 1985, 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.

Nevertheless, Ditka has contended that his reluctance to give Payton the ball was justified on account of the disproportionately heavy coverage the Bears' star running back faced from the Patriots' defense, and insisted that Payton's mere presence on the field was a decisive factor in the Bears' crushing victory notwithstanding personal statistics.

With the Bears trailing by three touchdowns in a late-season Monday night game against the Miami Dolphins, the team's only loss, Ryan finally snapped after Ditka, as he recounted in 2006 for NFL Network, told him that the defensive scheme was not working.

[29] The NFL Network series America's Game rated the 1985 Bears as the second-best Super Bowl champion, only behind the 1972 Miami Dolphins.

The first of those years saw the Bears finish the regular season with a 14–2 record to tie the eventual Super Bowl champion New York Giants for the best in the entire league.

[31] In 1997, after a four-year absence in which he had served as a television analyst, Ditka returned to the NFL to take over as the permanent replacement for Jim Mora with the New Orleans Saints.

Still, they were in playoff contention toward the end of the season, and defeated the eventual NFC East champions in Ditka's other former squad, the Dallas Cowboys, to get to 6–7 with three games to go.

After winning the season opener against the Carolina Panthers, the Saints dropped their next seven games, including a loss to the expansion Cleveland Browns.

After a late-season practice with the team sitting at 2–7, a grumpy Ditka gave a sixty-second press conference where he was very short tempered and dismissive of what he thought were stupid questions.

He also cited the Saints’ lack of playmaking ability, as they dropped several passes and failed to take advantage of three Falcons fumbles while turning the ball over seven times themselves.

In his first NFL start, Delhomme threw for two touchdowns and ran for a third, and Fred Weary took a forced fumble 56 yards for the game-winning score, as the Saints knocked off the Cowboys, 31–24.

He wrote Ditka: An Autobiography with friend and sports journalist Don Pierson;[36] he authored The 85 Bears: We Were the Greatest with Rick Telander.

[45] Ditka has made guest appearances and cameos on several other shows, including L.A. Law, Saturday Night Live and 3rd Rock from the Sun.

In 2005, Ditka had a major role in the comedy Kicking & Screaming, playing himself; he was recruited by Will Ferrell's character to be an assistant little league soccer coach.

Ditka performed "Take Me Out to the Ballgame" during a Chicago Cubs game at Wrigley Field in 1998, the first season after the death of Harry Caray, who had previously led the song.

Angry at the wealthy NFL for ignoring the players who helped to create the league, Ditka and other former players have since been attempting to raise funds, in the words of Hall of Famer Joe DeLamielleure, "for guys who made this league and built it on their backs, their knees, their legs and now they're all broken down and they can't even get a decent pension.

"[47] Ultimately, however, in December 2007, Ditka folded his "Hall of Fame Assistance Trust Fund" charity amidst revelations that, "in 2005, the group gave out more money to pay celebrities to play golf than the group in its entire three years of operation gave out to injured players", according to Laurie Styron of the American Institute of Philanthropy.

Local and national political leaders, from Illinois Republican Party Chair Judy Baar Topinka to National Republican Senatorial Committee Chair George Allen, whose father by the same name was an assistant coach with the Bears in the 1960s when Ditka played, met with Ditka in an effort to persuade him to fill the spot on the ticket.

[72] In stark contrast to the above-stated positions, Ditka appeared in an ad during the 2010 Illinois gubernatorial election for incumbent Democratic governor Pat Quinn.