Sometimes, a joke goes too far—and in the case of Missouri prosecutor Tom Hollingsworth, it cost him everything. The former Jefferson County Assistant Prosecutor pulled a “prank” that set off a chain reaction ending in professional ruin.
It all started in 2023 during a courtroom session. Hollingsworth and other attorneys were waiting their turn when an assistant public defender stepped out, leaving their laptop unattended. Seizing the opportunity, Hollingsworth sent an email to the county sheriff from the public defender’s account, cheekily stating, “You look sooooo good in khaki pants and that black shirt.”
Funny? Maybe. Career-ending? Definitely.
When the prank was uncovered, the fallout wasn’t limited to embarrassment. The Missouri Supreme Court got involved, pointing out the severity of Hollingsworth’s actions. Beyond the email, he had gained unauthorized access to all the public defender’s client files in the Hillsboro trial office—a serious breach of ethics and privacy.
As the dominoes fell, Hollingsworth was disqualified from handling 19 cases, with his legal career effectively derailed. The Missouri Supreme Court suspended his law license indefinitely, citing his reckless behavior and breach of trust.
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