Jenna Bush Hager Felt Like a 'Failure' After Her 'Underage Drinking' Habits Sparked Scrutiny

Jenna Bush Hager is scarred by a negative headline once written about her.

During the Thursday, May 7, episode of TODAY With Jenna & Sheinelle, the host, 44, admitted she still thinks about past media coverage of her underage drinking days in college.

Co-host Sheinelle Jones asked her friend if she’s ever had a “big disappointment or failure.”

“When I was on the cover of People magazine for underage drinking,” she teased. “That type of failure? Is that the type of failure you’re referring to?”

Jones asked how it made her feel reading headlines about her behavior.

“Not great at the time, but I actually think it was such an important part of my life…it said, ‘Oops, they did it again,’” she recalled. “It was very ‘90s, early aughts. There was also a cover that called me ‘Jen and Tonic.’ They were ruthless back in the ‘90s. But I would say failing is one of the most important parts of life. If you don’t fail, you don’t learn to have grit.”

Jones emphasized that now, Bush Hager has a “hit me” mentality where she “doesn’t care” what anyone says about her.

“I think it makes you stronger, and it also makes you very likable,” she elaborated.

“I’m not so likable back then with my folks,” quipped Bush Hager, who is the daughter of George W. Bush and Laura Bush.

While her father was president, Jenna was arrested twice. In April 2001, she was charged with possession of alcohol as a minor in Texas. One month later, she was again handcuffed after using a fake ID to buy drinks.

During an August 2025 episode of Today, Craig Melvin teased his costar about her misdemeanors.

"I recall reading articles many years ago about you getting away with a fair amount," he said.

Jenna insisted that she "didn't get away with it.”

"I was arrested! There’s a mugshot that says I didn’t get away with it," she exclaimed, then clarified, "No, I wasn’t really arrested like that."

In 2023, the media personality explained what really happened during her run-in with the law.

"I didn’t actually go to jail, I just was arrested," she told Hoda Kotb at the time. "I wasn’t even arrested; I was never detained. I just got a minor in possession of alcohol when I was 20 years old because I ordered a margarita at Chuy’s with a fake ID."

The waitress at the restaurant allegedly called the police to spite Jenna because she didn't like George.

"To her credit, that was dumb," the 44-year-old expressed. "I mean, my dad was the president [at the time]."