Monday, December 22, 2025

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Shocking Connection Revealed Between Bill Belichick And Bears

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Nobody disputes that Bill Belichick will end up in the Hall of Fame five years after he retires. The six-time Super Bowl winner is arguably the greatest coach in NFL history. Architect of the league’s greatest dynasty. Now he is chasing history. With his win over Cleveland last week, he reached the milestone of 324 career victories, tying him with iconic Chicago Bears founder George Halas for the second-most all-time.

It’s rather poetic he will seek to take sole possession of that spot tonight in Foxborough against the Bears. Belichick is a football historian. He delights in talking about the old days and deeply respects and admires Halas. People might be shocked to hear that the New England Patriots head coach has deeper ties to the man than you’d think. In his latest column, Mike Reiss of ESPN dropped some wild details before Monday Night Football.

Belichick’s ties to Halas came through his father, Steve, the longtime college football coach who knew some of the assistants on Halas’ staff in the 1950s and 1960s. Steve Belichick had also coached quarterback Bill Wade at Vanderbilt before Wade went on to play for Halas’ Bears, helping lead them to the 1963 NFL championship.

The Belichicks were based in Annapolis, Maryland, so when the Bears visited the Baltimore Colts, further connections were made.

We would go to the locker room after the game. They were always very gracious and generous, let me hang around and stuff like that,” Belichick recalled. “I have a ton of respect for Coach Halas and the McCaskey family and what he did for professional football.”

Bill Belichick came close to joining the Bears.

In 1999, Chicago fired Dave Wannstedt after his second straight 4-12 season. They needed a new head coach. The New York Jets were fresh off reaching the AFC Championship and their defensive coordinator, Belichick, was a big reason for that success. The Bears reportedly interviewed him, according to longtime insider John Mullin. It must not have gone how then-team chairman Michael McCaskey wanted. The Bears opted for Arizona Cardinals defensive coordinator Dave McGinnis, who they claimed accepted the job but soon found out they were mistaken when he withdrew his name from consideration. That forced a pivot to Dick Jauron instead.

After another year in New York, Bill Belichick was promoted to head coach after Bill Parcells resigned. That didn’t last long before Belichick did the same and was eventually traded to the Patriots. The rest is history. It is difficult not to wonder what if. Maybe the 2000s would’ve been so different for the Bears had they recognized what Belichick had to offer. Sadly their ability to recognize coaching talent has always been a central part of their failures for the past 30 years.

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