Chicago Bears quarterback Caleb Williams is heading into his second year in the NFL. While his first season resulted in a 5-12 record, expectations for this team have increased drastically this off-season. New head coach Ben Johnson has added a substantial amount of talent on both sides of the ball and the fan base has noticed.
However, the 23-year-old is currently facing some embarrassing backlash after trying to tattoo a fan.
“That Looks Horrible” Bears’ Caleb Williams Tattoos Fan, Fallout Embarrassing (Picture)

Caleb Williams displayed his tattooing skills during the off-season:
Music video director and record executive Cole Bennett posted a series of Instagram photos featuring Williams giving him a tattoo of the Bears’ logo on his left shoulder.
Bennett was an outspoken fan of Williams throughout his rookie season with the Bears.
The pair showed up on stage together at Bennett’s recent Lyrical Lemonade Summer Smash Festival in Bridgeview, Illinois and had a social media exchange afterwards.
The signal-caller showed promise as a rookie despite getting sacked a league-leading 68 times and the Bears finishing with a 5-12 record.

Williams completed 62.5 percent of his throws for 3,541 yards and 20 touchdowns compared to six interceptions. He ended his inaugural campaign on a high note, racking up 1,525 yards and 11 touchdowns while getting picked off once over his final seven appearances.
As Williams prepares for his second season under center in Chicago, he took some time to give Bennett a Bears-themed tattoo.

Fans were quick to react to this picture:
That looks horrible
— McQuade Arnold – WISports (@mcquadewarnold) July 14, 2025
Caleb face 🤣🤣
— the last + left (@newjerseyplus) July 13, 2025
🤣
— Granimal_Farming (@HigherEdCanna) July 13, 2025
Alright now step in here and hold the tattoo pen just like that….. perfect 📸
— Granimal_Farming (@HigherEdCanna) July 13, 2025

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