Caleb Williams Received a Lesson in Humbleness from Ex-NFL Quarterback Boomer Esiason: “Keep Your Mouth Shut”
Boomer Esiason wants Caleb Williams to get his act together and play football instead of complaining.

Caleb Williams (Image via IMAGO)
It doesn’t take much for Boomer Esiason to lose his cool these days. But his rage reached a new high when discussing Caleb Williams and the Chicago Bears.
Esiason never played against the Bears’ direct rivals unless fans consider the Cardinals as one. The former NFL MVP caught wind of the latest streak news seeping out of Halas Hall.
In his upcoming book American Kings: A Biography of the Quarterback, ESPN’s Seth Wickersham wrote about the troubled 15 months of Caleb Williams’ life. The 23-year-old’s father, Carl, didn’t want his son to play in Chicago. They allegedly tried to blindside the Bears organization by dropping to the UFL and trying their luck in 2025.
Boomer Esiason was not at all happy with the revelation. He criticized Williams for his ‘entitled’ attitude on the latest segment of the ‘Boomer and Gio Show’ on WFAN.
Keep your mouth shut. You’re going into the greatest league that there’s ever been for the sport we all love. You’re going to have a chance one day to make $500 million because guys like me and guys before me all went on strike so you could actually make more money. So keep your piehole shut and go out and play football and earn your keep and earn your respect.
Williams Sr. never shied away from pulling all the stops, from hijacking his son’s move to the Bears before the 2024 NFL draft. The NFC North team held the first overall pick, and every mock draft mocked the former Heisman Trophy winner ending up in Chicago.
Boomer went off on Caleb Williams amid reports that he wanted to avoid the Bears to the point where he and his family looked to sidestep the CBA 😳 pic.twitter.com/Tk6N1zQXSa
— WFAN Sports Radio (@WFAN660) May 16, 2025
Offensive coordinator Shane Waldron didn’t strike Williams as the type capable of unlocking his potential. Despite Williams’ prowess as a player, he felt alienated in Chicago and reflected on his play. Midway through the year, the Bears fired both Waldron and head coach Matt Eberflus.
Caleb Williams received support from former NFL quarterbacks
Williams’ share may have gone down in Boomer’s eyes, but not everyone views him the same way. Former NFL quarterback turned ESPN analyst Dan Orlovsky reacted to Wickersham’s report.

There’s obviously a big piece of his reluctance to go to Chicago. My big takeaway is – no one was watching film with him. No one taught him how to watch film, taught him what to look for, what to study at the defensive level in the NFL. If that’s true, that’s a disgrace.
We wonder why young QBs fail!!?
— Dan Orlovsky (@danorlovsky7) May 15, 2025
(I lived this as a young qb at times also) pic.twitter.com/PGV1PQsKUF
Chase Daniel, who spent several years in the NFL as a backup quarterback, called Williams’ situation ‘insane.’ In a X video, Daniel explained his method of reviewing tape.
He assigned each day of the week to a different part of the tape—Tuesday for first and second down. Wednesday for third down because the following day, the team will run the drill in practice. On Thursday, after practice, Daniel advised Williams and any other rookie quarterbacks to “watch third-down (defensive) pressures and you’re going to watch third-down blitzes.”
Caleb Williams not knowing how to watch film or what to watch is a complete disaster.
— Chase Daniel (@ChaseDaniel) May 15, 2025
Let me tell you EXACTLY how you need to watch film as an NFL QB & it’s exactly what Drew Brees taught me ⤵️ pic.twitter.com/voVxrUVJZF
Despite not receiving much support from the Bears in his rookie season, Williams showed why he was taken first overall in the draft. He completed 63.5% of his passes for 20 touchdowns and only 6 interceptions.
The Bears appointed former Detroit Lions offensive coordinator Ben Johnson. Johnson helped Jared Goff rediscover his form, earning him a $50 million+ contract extension. The Bears want Johnson to wave his magic wand and help Williams reach his true potential.
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