https://www.techdirt.com/articles/20180718/09500040261/university-illinois-bullies-alum-out-making-make-illinois-great-again-shirts-through-tiny-settlement.shtml

You will recall that earlier this year we discussed the University of Illinois' attempt to trademark bully an alumnus out of making orange and black shirts that read "Make Illinois Great Again." The whole story surrounding the school's actions is somewhat more complicated than it might appear. Part of the issue is that the shirts in question used the image of Chief Illiniwek, something of a mascot the school abandoned a decade ago, and one that was the source of controversy given its cartoonish mannerisms as related to Native American tribes. So, when the school first objected to Ted O'Malley's trademark application, and then later filed suit against him, you should understand that it was done as the school remains under public pressure to disavow the previous use of this imagery. All of that being said, claims that the school's trademark gives it the right to control the word "Illinois" on all apparel were obviously silly.

But trademark bullying works, as we've stated many times in the past. And it tends to work all the more when the bully has a large war chest to fund its legal team and the victim is a much smaller, much less well-funded entity. Such appears to be the case with O'Malley, who has settled with the school and essentially agreed to its demands in return for a measly $7,500 payout.