“Segway Boy” Protester Habitual Lawbreaker

By: Brian Sikma

Jeremy Ryan is a habitual loser, or, to borrow a phrase from state Senator Glen Grothman, a slob. Ryan is known around Madison as the “Segway Boy” after his distinct mode of transportation that has made him nearly ubiquitous in the professional protest circuit of the city. Chances are, if you visited the state capitol at all since the protests were at their height this past spring, you’ve seen Ryan riding a Segway around the downtown area, or getting hauled out of the Senate or Assembly galleries after violating gallery rules with his antics.

Ryan’s public record as a protester has been well documented. Many of his protests have landed him citations from the police because he broke various ordinances, rules and laws related to public disturbances and public conduct. According to a Milwaukee Journal-Sentinel article in June, Ryan had received 15 citations and been arrested nine times in conjunction with his protesting. The 15 citations had, as of June, racked up a total of $3,604.50 in fines – not a penny of which Ryan seems to be intent on paying.

As a professional, full-time protestor Ryan has no income from a job. What little money he does seem able to scrape up through donations apparently goes to pay for medication that he needs to manage several health issues as well as fund his political action committee, Defending Wisconsin PAC. The PAC does not pay Ryan for his work as executive director. GAB documents show that the committee has raised $8,305.90, and had $4,452.08 still in the bank as of its latest report. Perhaps if Ryan collected a one-time salary from his PAC he could be responsible and pay his outstanding fines.

The state of Ryan’s personal finances can be determined on almost any given day by the pleas for money that he issues on his personal Facebook page. Interspersed between requests for people to help him land speaking engagements are updates about his financial status. His requests tend to generate responses from sympathetic friends and supporters who indicate that they have contributed to his bank account through a handy web portal that he set up.

Court records show that Jeremy Ryan’s financial and legal troubles didn’t start around the time of the spring protests. They started back in 2007 (around the time he would have been 18 or 19), with an eviction battle that he and his apparent then-girlfriend, Tatiana Castaneda, lost. They were evicted because of over $5,000 in unpaid rent. A mere five months later they lost another eviction battle because of over $4,200 in unpaid rent. Not long after the second eviction, Wisconsin Power and Light went after Ryan for his accumulated unpaid electric bill. Ryan was ordered to pay Wisconsin Power and Light $688.83 over a year after the suit was filed.

Another case, this time in July of 2009, involved a domestic dispute and temporary restraining order for Ryan. The plantiff’s name is not part of the available record, but another case dating from a month and a half later in August of 2009 documents a paternity dispute between Ryan and his ex-girlfriend, who was also his co-defendant in the eviction cases.

The final non-protest related case in Ryan’s history is a claim brought against him on November 17, 2010 by the company that owns Rocky Rococo, a regional pizza and pasta restaurant chain. The case settled with Ryan owing the company $617.13. Whether the money was owed for pizza and pasta purchased or something else is not clear.

In a recent story in the Madison State-Journal, the deputy district attorney of Dane County, Chris Freeman, cited “limited resources” when asked why the Dane County District Attorney’s office was not pursuing charges against some of the more outrageous and misbehaved protesters. It is understandable that not every protester who may accidentally violate a minor noise ordinance would be subject to prosecution. But some, like Miles Kristin (who poured beer on GOP lawmakers), and Jeremy Ryan, are habitual and knowing lawbreakers. Their inability to be responsible in other areas of life leaves them with fewer excuses to justify their wrong behavior.

If Mr. Freeman, and his boss District Attorney Ismael Ozanne, are serious about wisely using limited resources, they will enforce the law on habitual lawbreakers like Ryan, Kristin and others. Their job is to enforce the law and keep the public safe. Excusing the actions of irresponsible protesters isn’t a wise use of limited resources: it is a tacit endorsement of illegal behavior and an abdication of the responsibilities of the office of District Attorney.


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