Question of the Day: Which All-Time Chicago Bears Players Would You Draft for a Flag Football Team?

It’s official! Flag Football is an Olympic sport that NFL players can participate in! Which current or former Bears would you roster on such a squad?

After my attempts at becoming a professional football player failed, I turned my attention to flag football and was fortunate enough to play in three national tournaments in my college days. Having won numerous championships at various levels and tournaments, I never won on the nation’s biggest stage.

And then flag football blew up.

Now official: NFL owners voted today to permit players to participate in flag football at the 2028 summer Olympics in Los Angeles. pic.twitter.com/KiZoq1QdRn

— Adam Schefter (@AdamSchefter) May 20, 2025

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You can now watch flag football on ESPN, and it has recently been named an Olympic sport, which got me thinking…

Which Chicago Bears players would you select on a 5v5 flag football team?

I will go first.

QB: Caleb Williams – While Justin Fields may get the nod for most people here, I am going with Caleb. Not only can he make all the throws, but his agility, quickness and speed are underrated aspects of his game and will make defending him near impossible.

Chicago Bears v Green Bay Packers — Caleb’s ability to use his legs to avoid pressure and throw on the run would be diabolical in flag football.

WR/DB: Devin Hester – this one was easy. Hester is arguably the most elusive player of all time, any position, and has experience playing on both sides of the ball.

Green Bay Packers v Chicago Bears — Not only could Hester avoid people, but most often he did so without being touched. In flag football, that would be lethal.

WR/DB: Brandon Marshall – B-Marsh was another easy call. Not much you can do when the ball is thrown up to a 6’5” phenom, but many people didn’t also know Brandon played some Safety in college at UCF. He would be a stud.

Chicago Bears v Detroit Lions — An underrated athlete for his size with plenty of make-you-miss ability, B-Marsh would be unstoppable in flag football with his routine ability to “Moss” defenders.

WR/DB: Tim Jennings – Tim Jennings was one of the fastest DBs in Bears history, having run a 4.34 forty at the 2006 NFL combine. He also had excellent hands, as evidenced by his league-leading 9 interceptions in the 2012 NFL season. He would be a lockdown CB for us.

Chicago Bears v Oakland Raiders — An explosive athlete with top-notch cover skills in his prime and exceptional hands, Tim Jennings would lead the Bears Defense in flag football.

RB/DB/C: Walter Payton – Sweetness not only personified selflessness, but was also a phenomenal athlete with a well-rounded game. I would expect him to snap the football and use his agility/vision and hands to quickly become an asset to Caleb in the short passing game while also being a leader on defense.

Walter Payton Runs Against Kansas City Chiefs — Watching “Sweetness” avoid defenders in flag-football would be poetry in motion much like it was on the gridiron. But perhaps even more fun would be watching him compete on defense.

Reserve: Tarik Cohen – Rik would be a nightmare for opposing defenses to catch. He’d also be a legit pass rush threat. My main concern with him is his coverage ability and size on defense. But trying to pull his flag would not be fun.

NFL: Minnesota Vikings at Chicago Bears — Cohen’s low center of gravity, elite agility and burst are made for flag football.

What about you? Which 5 past or present Chicago Bears players would make your flag-football team?