Chicago strongman would be that by a load of measures, we're all better off in an absolute sense. Fewer kids dying, easier to treat disease, everyone is consuming more stuff. All due to various liberalizations ranging from tax cuts to less regulation (City / Big Bang) and generally less of the state. There's lots of opportunity to do stuff, generated by this fantastic economy. I think I lean more to the right than most people, and that's more or less the summary on that side.
My take is that absolute wealth hardly matters to most people. It's always been a question why Bob gets more than Alice, regardless of whether they lived in the stone age or the information age. People care about relative status a heck of a lot, and they will keep doing so. If absolute wealth were all that mattered, nobody would complain anymore because we all have much more than people of not long ago, and insanely much more than stone age people.
Look at various struggles between people of different status throughout history. The Barons and the Magna Carta (John), the French Revolution, the general strikes of the 20th century. All of them are somehow about what relative status people have, yet it makes no sense from an absolute point of view. The 20th century miners for instance had free healthcare and running water toilets, which the Barons and French aristocrats didn't have. Only the lens of relative disparity, aka common sense, explains it.
So if I now look at some factory worker in China, who is doing better than all her ancestors, do I take the view that she's simply spoiled and complaining too much? Not really.
The 99% strongman is, well, look at it: you can't even run for office in America without being really, really rich. Lobbying is a legit career. The wealthy are approaching gilded ages levels of relative wealth, and that buys power. There's no formal slavery, but loads of people are on a precarious treadmill, forcing them into negotiations that are only slightly better than slavery. You don't get whipped, and you're allowed to vote, but only for whichever rich guys are on the ballot. You'll never really be allowed to work your way up, because you need capital to grow capital, and you're not gonna get any.
What's wrong with this argument? Well there is a bit of choice at various levels in the tree. If you're on minimum wage, there's more than one thing you can do for that wage. A bit higher up the chain, a software dev has a bit of choice over who employs him, and can often take a break from the career. With a little luck you might also be able to get funded for your own shot at being wealthy.