In 1988 Chicago made a 30-second ad to call visitors home. A cab pulls up to a bar on Division Street. A man who’d left for California walks in. Mike Ditka looks up from his table and says one word, his old friend’s last name. Dick Butkus answers with his. On Friday, Ditka’s family said he had died. He was 86. He’d moved back to Chicago for good a few years ago.
Jason Gay’s obituary in the Journal covers a lot of ground. Ditka played, coached and made the Hall of Fame twice, in college and the pros. He sold products on TV, worked as an analyst and acted, as long as the part was himself. There were restaurants, wine and tobacco. Some ventures worked and some didn’t, and he got up every time. He came out of Aliquippa, Pennsylvania, a steel town, on football. As a tight end he played for the Bears, Eagles and Cowboys. Gay quotes his best line. “If God had wanted man to play soccer, he wouldn’t have given us arms.”
His peak came in Chicago. He played for the Bears in the 1960s and coached them in the 1980s. The 1985 team, with Walter Payton, Fridge Perry and Jim McMahon, went 18-1 and crushed New England in Super Bowl XX. Those Bears cut a bragging record before the playoffs even started, then won it all. Ditka let the song slide, and McMahon’s fights with the league over the dress code too. His own look was a dress shirt, a tie and a sweater vest with the team’s name stitched across the chest. Saturday Night Live built a sketch around the city’s love for him.
A whole draft for one player
New Orleans went worse. The Saints went 6-10 twice under him. Then Ditka sent every one of the team’s 1999 draft picks away for one man, Texas running back Ricky Williams. The season ended 3-13, and his NFL coaching career ended with it. Public life kept him busy. A long run of commercials, a Will Ferrell comedy, and in 2004 a possible Senate run against Barack Obama. He thought about it and said no, and later said he wished he’d run. The trade he never took back. He said he’d do it again.
He did come to regret something bigger. He’d watched football hurt people. Teammates, former players like McMahon and the late Dave Duerson, and himself. In 2015 someone asked if he’d let an 8-year-old son start playing. He said no. “And my whole life was football,” he added.
Our read
This is a risk story (Investments/Risk, IN04), and a behavior story. Ditka gave up a whole draft class for one exciting player. All the chips on one square. When it failed, the team had no draft class to fall back on and he had no job. And he said he’d do it again. We see the same thing in portfolios. One stock, one rental, one business, and a story about why this time is different. Never let one position decide the whole season. Write that rule down before you fall for the player.
There’s a retirement point too (Retirement, M10). He never coached in the NFL after that 1999 gamble. He lived until 2026. That’s a long second act, and he filled it with ads, restaurants and wine. He had a place in Florida. A few years ago he went home to Chicago for good. Where you spend your last years is part of the plan. His 2015 answer about a young son shows the cost side of the career. A review is where we ask both things. Name the one bet that could sink you. Name where you want to end up. It’s easier to find the umbrella while the sky is still blue.