Trump's dad gave him millions of dollars to start businesses and then left him somewhere near a billion when he died.
I think those are two pretty different upbringings!
She was indeed a congressional intern, but then her father died and family finances got rough, and a year later Ted Kennedy died (August 25, 2009) so she lost the job in his office.
> Following the financial crisis of 2008, tragedy struck when her father passed away suddenly from cancer. The medical bills and other growing expenses placed their home at risk of foreclosure. Alexandria pulled extra shifts to work as a waitress and bartender to support her family,
Her father seems to have been in the business of home remodeling and renovations. I haven't found any source for "owned multiple brownstones", but a little bit of house-flipping or some rental properties wouldn't be weird to see in that kind of business. Being a landlord with a mortgage doesn't necessarily mean huge wealth, and it it's easy to believe a combination of cancer treatment bills/being unable to work/2008 housing crisis could take a situation like that from comfortable to house-poor to foreclosure on upside-down loans in an awful hurry.
The actual land records that prove this are impossible to link, for reasons that are charitably described as "Monstrous incompetence of government officials".
This article talks about her dad's Bronx condo that she lived in, or claimed to live in. No offense to the people of the Bronx, but that is not a "rich" part of NYC. Units for sale in the building mentioned are rather cheap for NYC, in fact.