The Chicago Tribune probably felt Trump described Chicago.
Shitholes tend to remain shitholes since the inhabitants do not work to improve it.
As the Chosen Man noted:
There's no shame in being born in the shite, lads, but there's ever so much for wanting to stay in it.
--Sgt. Maj. Patrick Harper, South Essex
Apparently, it is the US's responsibility to transform these shitholes, some of whose transformation into shitholes were performed by European countries vying for colonies. But that would be "wrong" what with imposing US "ideals" upon others. In some ways, that could be a fair criticism of the missionary work. Instead, European countries--and pretty much all Asian countries--would rather the US simply move all of the inhabitants of said shitholes to America.
These are all nice slogans, with little actual solutions.
Though I am reminded that a very long time ago, someone I knew who was a freshly-made lieutenant, traveled to Haiti on one of Reagan's "mercy missions" or whathaveyou when that particular shithole got flushed by a hurricane or "Baby Doc" had an enema or something.
The first thing he saw getting off his transport plane was the charred body of a woman hung and burned as a witch.
Some things are hard to fix. Why politicians kick cans and spout slogans. They--from all countries including said shitholes--hate it when made to do