I read
a second article which paints a very different picture of the situation. From what I gather from it, the situation is this...
The law (that the price of attending an "amusement" within the city is taxable) was already on the books.
People who bought PSLs directly from the Bears have already paid this tax. However, anyone who bought a PSL from someone else who owned it, rather than from the team directly, has not.
The city recently asked the Bears to supply the names of "transferees" since 2004... that is, people who bought a PSL from another PSL owner rather than from the team directly.
The city then sent a letter to these people that said, "You were party to a transaction wherein a ... permanent seat license was transferred to you. Such a transaction is subject to the Chicago amusement tax as the amount paid was for the privilege of witnessing an amusement in the city."
The letter asked the PSL holders to complete and return an attached affidavit "that will assist us in determining the amount to bill for this transaction."
If the affidavit is returned within 45 days and the debt is paid 30 days after billing, "The amount ... will include only the tax amount due," the letter states. If not, a 12 percent annual interest and penalties will be applied.
It doesn't sound like the situation is as bad as the article in the OP makes it out to be. This isn't a case of ex post facto taxation, the tax was previously levied and was being charged to people. But sales between private citizens were made without the tax being paid. I'd say the city/county is in the right in being able to go collect this. One can argue the seller is responsible and maybe there's a case there, though as far as what is "right" it would be the buyer who
should be paying it, so I think situation is already about as just as can be with them contacting the buyers for the payment.
One can still argue whether a PSL should be taxed under this amusement law in the first place, but that seems a separate argument.