With his head down on the table, dressed in his infamous hoodie, black mask and sunglasses, “Chalk Guy” (Henry Contreras) remained silent as he stood before a judge. 

On Wednesday, January 28, at 3:00 p.m., Contreras attempted to challenge the $5000 fine the city of Walla Walla had imposed on him for breaking the city’s Municipal Ordinance A-2405. He had been found liable on ten separate infractions for not removing his sidewalk chalk messages within a 24-hour window, according to Assistant City Attorney June Riley. 

Outside of the courthouse, messages such as “End victimless laws” and “Disobey unjust laws” were scattered on the steps. 

Contrares defended himself. Equipped with a rebuttal that the city had filed his paperwork incorrectly, the judge denied his motion.

“Have they signed the court order demanding I pay the money?” Contrares said.

These were the only words he spoke. Once the judge reinstated that he had been found to be held liable, he went quiet. 

After this moment, Contreras refused to address the court and sat with his head down, scribbling words on a piece of paper in front of him. The judge eventually had to put on record that Contreras was unresponsive to questioning.

With his hope eventually crushed, members of the community stand divided on the chalk ordinance itself and the hearing.

One such member is Andrew Hunt, 40, who started a GoFundMe for Contreras. 

“I created the GoFundMe strictly for finding Henry a lawyer, to fight these outrageous fines, and defeat a city ordinance that is targeting one man!” Hunt said.

Contreras, because it is a civil infraction and not a criminal trial, is not provided with a state-sponsored lawyer. This concerns Hunt, who believes that this hearing should be about the constitutionality of the ordinance, not if the city had provided the correct paperwork, as Contreras argued in court.

Hunt and Contreras have an exchange-based relationship, rather than a friendship, as he supports his constitutional right from the sidelines and they strictly talk about the chalk ordinance. Hunt remains steadfast in his belief that the chalk ordinance violates free speech.

“Henry has only peacefully protested his government,” Hunt said. “But we live in a time where our dear leaders can intentionally misinterpret a situation to create a narrative, and then attack our freedoms in the name of safety, and people eat it up.” 

On Whitman College’s campus, students hold a more nuanced perspective than Hunt, balancing what they believe is offensive speech with his right to express himself. 

Seniors Maille Moynahan and Caine Ryan expressed these ideas. 

“I think it’s pretty difficult to enjoy a peaceful day downtown when it’s disrupted by these hateful messages,” said Moynahan. “But I think that if we target this message and say we should make rules against this, it can be used very easily towards [any kind of] protests that I agree with. So it’s kind of a balance there.”

Ryan shares a similar sentiment.

“I personally have a lot of problems with him,” he said. “But I also don’t know if I necessarily agree with the city’s decision to really target him – it doesn’t feel like the best way to encourage free speech on all sides.”

The city’s attempts to restrict the use of chalk have simultaneously led people to believe that it had targeted Contreras in particular, but also poses the potential of consequences for chalk messages that others deem as counter-speech.

The two students also shared concerns that his mental well-being was a contributing factor to his constant chalking and potential financial burdens that could inhibit his ability to pay the fines. 

“I feel like something that is problematic to me is hitting people that are already kind of struggling [mentally and] financially,” said Moynahan. 

The Chalk Ordinance itself was created to protect businesses and the city’s influx of tourists drawn in from the flourishing wine industry. The City of Walla Walla spent $13,188 in 2024 to remove chalk messages from sidewalks, and this fine is intended to compensate the workers who dedicated their day to cleaning the messages. 

This fact is what leaves Hunt unsatisfied. He believes that the city is protecting businesses and tourism first, and leaving the First Amendment as an oversight. 

When asked about her perspective on the ordinance, Assistant City Attorney June Riley stood firm in their neutrality to the case.

“My opinion doesn’t matter,” Riley said. “I’m here to enforce the city’s ordinances, and that’s what I do, and this is an ordinance passed by the city, so I just do my job.”

Following the hearing, community members are uncertain if this ordinance will have any impact on Contreras’ behavior. 

“People just keep giving him confrontations and harassment, and that adds to content,” Hunt said. “As long as he has content, he will continue.”

“He knows people don’t like him. He knows the city is kind of trying to come after him,” said Ryan. “Now he can be a victim with the whole ordinances and everything.”

With Contreras at a standstill, the general public continues to question the validity, purpose and effectiveness of the city’s Chalk Ordinance.