Milwaukee 'Dating Predator' Suspect to Represent Himself at Trial

Timothy Olson, accused of kidnapping and linked to two deaths, will act as his own lawyer despite warnings from legal experts.

Published on Feb. 21, 2026

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Timothy Olson, a man Milwaukee-area investigators have called a "dating app predator," is set to represent himself at his upcoming criminal trial on March 9. Olson has been jailed since late 2022 after being accused of kidnapping a 79-year-old woman and using her cards, and prosecutors have also tied him to suspicious deaths in Racine and South Milwaukee. Despite warnings from legal experts that self-representation is unwise, especially in serious cases, a judge has agreed to allow Olson to act as his own lawyer after he petitioned from jail.

Why it matters

The case has drawn significant attention due to the serious nature of the allegations against Olson and the concerns raised by victims and legal experts about the potential risks of him representing himself. The decision to allow self-representation raises questions about the court's handling of competency issues and the rights of defendants, especially in high-profile cases involving vulnerable victims.

The details

Olson has moved through several defense attorneys since his 2022 arrest, with his trial still scheduled for March 9. Franklin police arrested him in November 2022 after investigators say he forced a 79-year-old woman into her car at gunpoint, drove her to ATMs, and used her cards. Prosecutors later filed kidnapping, burglary, and related charges. Investigators in Racine and South Milwaukee have also identified Olson as a person of interest in two death investigations. Despite warnings from legal experts about the risks of self-representation, a Milwaukee County judge has agreed to let Olson act as his own lawyer after he petitioned from jail, and a doctor's report on his competency is expected next week.

  • Olson was arrested in November 2022.
  • Olson's trial is currently scheduled to start on March 9, 2026.

The players

Timothy Olson

The man Milwaukee-area investigators have called a "dating app predator" who is accused of kidnapping a 79-year-old woman and using her cards, and has also been tied to suspicious deaths in Racine and South Milwaukee.

Franklin Police

The police department that arrested Olson in November 2022 after investigators say he forced a 79-year-old woman into her car at gunpoint, drove her to ATMs, and used her cards.

Milwaukee County Judge

The judge who has agreed to let Olson act as his own lawyer after he petitioned from jail, despite warnings from legal experts about the risks of self-representation.

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What they’re saying

“No one should represent themselves pro se in a criminal case, especially one as serious as Tim Olson is looking at.”

— Dan Adams, 12 News legal analyst (WISN)

What’s next

A doctor's report on Olson's competency is expected next week, and the trial is still scheduled to start on March 9, 2026.

The takeaway

The decision to allow Olson to represent himself, despite warnings from legal experts, raises concerns about the court's handling of competency issues and the rights of defendants, especially in high-profile cases involving vulnerable victims. This case highlights the complex balance between a defendant's right to self-representation and the need to ensure a fair trial, particularly in serious criminal prosecutions.