I think I filed about 60 cases in total. So, off the top of my head... one that is still ongoing is that newspapers are banned inside the Cook County Jail for "security" reasons. You actually have a Constitutional right to access newspapers under the 1st Amendment, but that doesn't stop an agency from blocking this right and then making you sue them.

The primary reasons given by detention facilities for blocking newspapers are fire, flooding, gang information and hidden messages in classifieds. The argument is that newspapers are easy to burn, that you can block the toilets with them, that you can find out what gang members are upto and that you can get messages from the outside (all communications are monitored in custody).

These excuses used to be taken as gospel by the courts, but lately there has been a little pushback from the rare judge. Fires have been ruled out - you usually have books, magazines, legal work that you can burn instead. Flooding is ruled out - you can use clothing, towels, sheets, blankets instead, and of course, other paper goods. Messages can be hidden inside magazine ads too, and magazines are usually allowed. Gang information - well, you can get this from the TV and telephone. I don't know a single gang member who wants a newspaper to get gang information. They just call their people on the telephone.

This was a similar suit won against the same jail a few years ago:
http://archive.today/2021.10.23-004355/https://www.prisonleg...

One suit I won $1000 for was because I used a Freedom of Information law to try to get the disciplinary record of my arresting officer because the prosecutor told me he was bogus. I tried three times and the police refused to reply, so I sued and asked them to settle immediately. They gave me the records and offered me $500. I asked for $1300 and said I wanted them to bring me Five Guys cheeseburger and fries to the jail. They replied $1000 and "lunch is not part of the deal." So I got the cash at least.

They were giving us 45 minutes less sleep than they should, and an hour less than they should out of our cells during the day. I won that, which was a big logistical nightmare for the jail and sent me to the Hole for the 2nd time with a fake contraband charge.

I sued because they put you in the Hole without giving you a hearing to determine if you are guilty of any infraction. I lost that in the trial court and appeal court. They ruled that pretrial detainees can be punished for any reason without any justification.

I sued because county sheriffs in Illinois aren't bound by any limits on punishment. I'll explain. Crimes are regulated by statutes which tell you exactly what you should not do, in detail, and the punishment expected if you commit them. These statutes are written by democratically-elected lawmakers. In county jails the sheriffs make up all the "crimes" and the punishment. Anything they say is a crime. And they can assign any punishment. Therefore if you "cause a disturbance" (one stated crime which is so vague it can mean anything) they can punish you by sending you to the Hole. But they could also just get out a knife and chop your hand off. Or they could just shoot you dead on the spot. There is nothing to protect you right now. I sued to limit this, but the courts said the constitutional protections on proportional punishments (punishment must fit the crime) under the Illinois and federal constitutions do not apply to pretrial detainees in Illinois.

I tried to get workers comp for the people in the kitchen who had lost their fingers in the meatball-making machine, but the statute requires that you must be a "person performing a service for the Sheriff" to get workers comp and the Attorney General basically ruled that detainees do not fit the legal definition of a "person".

I could go on all night LOL