My Day as a Pollwatcher in Cook County Jail

Left to right: Tashiana Stafford, Kiah Sandler, and Alana Reyes Jones prepare to begin pollwatching at Cook County Jail.

This year, Cook County Jail for the first time operated as an election precinct, allowing eligible voters in pre-trial detention to cast their ballots in person. During the weekend of October 16-17, volunteers with Chicago Lawyers’ Committee and Chicago Votes entered the jail as pollwatchers to observe the general election and help protect voters’ rights. 

Legal Intern Alana Reyes Jones recalls her experience as a volunteer pollwatcher below.

For me, being a poll-watcher in Cook County Jail was both humbling and eye-opening. I woke up on Saturday morning feeling eager and gathered together everything I’d need for the day: A water bottle and a sandwich, a mask and some hand sanitizer, and a notebook to help me keep track of any issues with voting. I had been to the Jail before, but only as a visitor. This was my first time as a pollwatcher, and I wanted to be as prepared as possible. 

Cook County Jail is a sprawling campus in Little Village that houses almost 9,000 incarcerated community members, the vast majority of whom are Black and Latinx. I was assigned to pollwatch in Division 3 Annex, a women’s detention center that looks a little more modern from the outside than many of the jail’s other imposing gray buildings. I left my cell phone in my car and signed in at the front desk with the officers, who then escorted me to the voting room. 

Inside the room, election judges from the Chicago Board of Elections and the Cook County Clerk’s Office sat at their tables ready to receive and register voters. Several private voting booths had been set up around the room and the ballot boxes were set up near the exit. As I introduced myself and got to know them, I was happy to hear most of the election judges were veterans who seemed  mindful of common registration pitfalls for incarcerated voters, and knowledgeable about the voting process.

Around 9am, the correctional officers began to bring in groups of incarcerated voters to our room, separated by “tier” (or floor) and divided into Chicago and Cook County voters. I noticed that the election judges from Cook County were able to register new voters quickly, which made voting for suburban residents go smoothly. Unfortunately, the City’s election judges were experiencing technical difficulties with their computer program, which lasted for about two hours and delayed voters from accessing the ballot until about 11am. 

Delays like this are much more serious for incarcerated voters than for others, because they have such a restricted schedule and a limited time window in which to vote.  Although both the election judges and the voters were frustrated, everyone remained calm and worked diligently to get the system rebooted. Once they were back online, the election judges thanked the voters for their patience and voting resumed. At 5pm, I counted about 10 voters who voted with Cook County and about 25 voters who voted with the City of Chicago.

Throughout the experience, I especially appreciated two women who worked hard to create a smooth voting experience. One of them, a young election judge, was adamant about sanitizing the ballot boxes, voting cards, and registration tables after every tier voted. She went above and beyond to ensure everyone’s safety that day. Another woman, the Sergeant on duty, was firm, conscientious, and helpful, which I expected. What I didn’t expect was her congenial spirit. She knew almost every detainee’s name and encouraged them each to make informed decisions and to feel good about claiming their voice at the ballot box. 

Many low-income folks who cannot afford to pay their pre-trial bond end up staying at Cook County Jail for long periods of time. My colleagues who pollwatched at other parts of the jail met voters who have been incarcerated between one and three years while waiting for a trial. Because of that fundamental injustice, it was inspiring to see women who have been stripped of most privileges prioritize voting. As they submitted their ballot to the election judge, I could only imagine what was going through their minds. 

I’ve volunteered in many spaces, but no other experience compares to seeing a first-time voter cast their ballot inside a jail. It was especially empowering to help voters understand some of the political jargon on their ballot. Many of the incarcerated women told me they were proud to exercise their right to vote, and I was grateful to witness it. I felt fortunate to be a pollwatcher in a place that many Americans don’t think about until they or someone they know is incarcerated.