The Kaiser shipyards in California, during WWII and after in the 50’s had paid/provided healthcare and many other bennies. They built the Liberty merchant/supply ships in the Pacific.
Henry Kaiser, german immigrant industrialist. Also, Kaiser aluminum, Kaiser steel, American Shipbuilding, and vast real estate holdings.
After the war, they developed the first private health maintenance org. for their employees, savings plans, stock share etc.
Surviving to day as ultra lib mega company Kaiser Permanente.
That the one?
Googling 'bankrupt company run by progressive' had waaaay too many hits to scroll through!