Timothy Olson, the man Milwaukee area investigators have called a “dating app predator,” is now set to speak for himself at his Milwaukee County criminal trial, which is currently scheduled to start March 9. Olson has been jailed since his late 2022 arrest, after Franklin police say he forced a 79-year-old woman into her car and used her cards, and prosecutors and investigators have also tied him to suspicious deaths in Racine and South Milwaukee. The case has dragged on while his legal team repeatedly changed and while the court has weighed his competency to stand trial.
Judge Signs Off on Self-Representation as Competency Review Looms
Online court records show 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 has sent multiple letters to the court asking to represent himself and has moved through several defense attorneys since 2022, with his trial still slated for March 9. “No one should represent themselves pro se in a criminal case, especially one as serious as Tim Olson is looking at,” 12 News legal analyst Dan Adams said, according to WISN.
Arrest in Franklin and the Wider Allegations
Franklin police arrested Olson in November 2022 after investigators say he forced a 79-year-old woman into her car at gunpoint, drove her to several 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 and warned women in the area that encounters with him sometimes left them disoriented or missing money. Details of the Franklin arrest and the Racine case link were reported by TMJ4, while Olson’s public denials were covered by FOX6.
Revolving-Door Defense and Victims on Edge
Court records and local reporting show Olson’s defense has been in constant flux, with multiple attorneys withdrawing or asking to withdraw since his arrest, a pattern that victims say has only deepened their frustration. A woman who said she was victimized years earlier told reporters she worries Olson could avoid accountability, and others have echoed concerns that the case is moving too slowly. Earlier coverage shows a judge rejected a previous request from Olson to represent himself in 2023 before this latest approval, a history and update that were detailed by CBS58.
What Going Pro Se Really Looks Like
The right to represent oneself in a criminal case is protected under the Constitution, but judges must make sure any decision to waive counsel is knowing and intelligent under Faretta v. California and related case law. Courts sometimes order psychiatric or competency evaluations when the record raises red flags. Self-representation can slow down a case, raise the odds of procedural mistakes and make it harder to handle evidence and witnesses, problems that legal researchers say are especially common in serious criminal prosecutions. For more background, see Oyez on Faretta and research from NCJRS on competency standards…