Deborah O'Keefe of Jason & Deb Sues 101X Owners Waterloo Media

Lawsuit alleges misogyny and discrimination by owner Bob Sinclair, station countersues

Waterloo Media's offices and studios in North Austin (photo by John Anderson)

Former 101X radio host Deb O'Keefe has filed a lawsuit against station owners Waterloo Media, seeking monetary relief of over $1 million. O'Keefe was fired in February 2021, following the 2019 acquisition of the station by Waterloo. The legal filing, obtained by the Chronicle, says Waterloo breached a contract agreement with the longtime host to keep working through the end of 2022.

The suit, filed back in Dec. 2021, also states: "101X's culture became toxic shortly after [Waterloo owner] Bob Sinclair began managing it. One way in which Bob Sinclair did this was by continually making misogynistic, racist, and discriminatory comments."

In March 2022, Waterloo filed an answer with the court denying "each and every allegation" made by O'Keefe, followed by a September 2022 counterclaim saying the host had breached her own contract. According to the claim, O'Keefe was fired only after "she was issued eight written warnings … regarding excessive absences and habitual tardiness from December 2018 through January 2021." O'Keefe declined to comment to the Chronicle, and representatives of Waterloo did not respond to our requests for comment.

In addition to work performance, the station's counterclaim adds that O'Keefe also violated her contract by "publishing disparaging or damaging information concerning Waterloo on her public social media accounts." Following her 2021 firing, the longtime host posted online: "Our owner has extreme dislike for me, and used a petty reason to get rid of me … He is a petty, Trump loving moron, who has decimated our staff and affected our company [morale] horribly since he took over, and who has more money than sense."

A minority owner in the cluster of radio stations since 2003, Bob and David Sinclair's Waterloo Media is now the majority owner of eight Austin outlets: 101X Alternative Austin, Austin City Limits Radio, 103.5 Bob FM, ESPN 102.7, KLBJ-AM, KLBJ-FM, 107.1 La Z, and Lucy 93.3.

In 2006, O'Keefe joined as co-host of popular morning show Jason & Deb. Known for her British accent and crank phone calls getting strangers to say, "I love you," she won Best Radio Personality in the Chronicle's 2008 and 2009 Austin Music Awards, as noted in her lawsuit. The suit says she had a "great working relationship" with former owners Emmis Communications prior to the 2019 acquisition of 101X by Waterloo.

Describing Bob Sinclair's management style after taking over the business, O'Keefe's suit alleges that "in his first conversation with a female Hispanic employee who was born in Mexico, Bob Sinclair told her, 'If you slip up, I'm calling immigration.' … On other occasions Bob would jokingly ask if the Hispanic co-worker left her sombrero at home."

The lawsuit claims that Bob Sinclair "was willing to damage the careers of female employees in order to prop up the careers of male employees." Cited incidents include the alleged demotion of Melissa Vasquez "La Chilanga" at 107.1FM La Z, the firing of Imari Mora at KGSR 93.3FM, and the firing of 101X Marketing Director Berenice Guzman. The suit also states that, "When discussing issues related to 'The Jason and Deb Show,' Bob Sinclair would say that 'Jason wears the pants, so I'll talk to Jason about it.'"

Regarding accusations made by O'Keefe, an anonymous former Waterloo employee told the Chronicle that they have known Bob Sinclair to be both "sexist and racist," as well as to have "issues with employees' progressive politics."

Describing the time leading up to O'Keefe's departure, one passage of her lawsuit states:

"[O'Keefe] did not feel she could go to the Human Resources Department because Bob Sinclair appointed his nephew, Chris Sinclair, as head of HR at Waterloo. [O'Keefe] believes that nonetheless management reported [her] opposition to sexism and gender discrimination to Bob Sinclair. [She] believes Mr. Sinclair retaliated against her for that report. [She] was terminated by Bob Sinclair / Waterloo soon after …"

O'Keefe's suit accuses Waterloo of various violations of the Texas Labor Code, including a hostile work environment, age discrimination, disability discrimination, and gender discrimination. The document describes O'Keefe as a woman over the age of 40 with a "diagnosis of depression stemming from a head injury she suffered around 10-15 years ago." According to her petition, O'Keefe was approved for work leave in June 2020 "to receive inpatient treatment for depression and related alcohol abuse," ultimately taking four weeks off.

O'Keefe's suit says that she had to call in sick or late "on several occasions" because of depression and headaches, and concludes that Waterloo's "stated reason for firing [her] – tardiness – was pretext for discrimination." Waterloo's counterclaim argues the company rightfully fired the host following "excessive absences and habitual tardiness" over a period of multiple years. The company's countersuit further details O'Keefe's alleged breach of her contract agreement with Waterloo following multiple notices:

"O'Keefe breached the Agreement by failing or refusal to comply with Company rules, policies, or directives after receiving notice of such failures. O'Keefe further breached the Agreement through her unsatisfactory performance of obligations under the Agreement following thirty days' written notice and her subsequent failure to cure non-performance within [the time] period."

Following O'Keefe's 2021 firing, 101X rebranded the Jason & Deb morning show as Jason Dick & Friends. The show introduced Emily Svahn filling in beside Dick and co-host/producer Nick Hajda. O'Keefe launched her own podcast with local Hot Pie Media in 2021, which ran for less than a year.

Regarding the shift, O'Keefe's lawsuit states: "In 2021, Jason Dick was consistently tardy or absent, but was not fired … [O'Keefe's] position after her termination was offered to a 23-year-old female who had no professional on-air experience."

But in December 2022, Dick was also told his contract with the station would not be renewed. Asked about O'Keefe's court filing at the time, Dick told the Chronicle: "I cannot comment on the lawsuit other than to say it is my opinion our terminations are not related." The morning spot has yet again been rechristened as The Morning X, presumably accommodating any future shuffling of personnel.

"I don't think there's anyone actually managing over there anymore but Bob," the anonymous former employee told the Chronicle. "Not renewing contracts and letting go old hosts makes sense in this market, with as bad as radio is.

"Sinclair's gonna delay [the lawsuit] until O'Keefe can't afford it anymore, is my guess. It'll be interesting to see if others are subpoenaed. If I am, I'll certainly go."

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Deborah O'Keefe, Waterloo Media, 101X, Jason Dick, Bob Sinclair, Jason & Deb, Emily Svahn, Emmis Communications, Alternative Austin

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