The most awkward ad campaigns are always the ones that know that whatever it is they're pitching is kind of crappy. Usually, they just try to hide the crappiest bit and move on from there, like in the case of the Porsche Panamera. In the New York City Subway's case, they straight up said it was bad.
This series of ads was made in the late 1980s, when ridership on the subway was reaching record lows – and for good reason. For decades, the city's budget was even more horribly managed than it is now, with deficits and even a municipal bankruptcy. As a result, maintenance on the subway system was continually deferred, with a lot of the "shhhhhh, it'll be fine" sort of attitude going on.
All of that procrastination finally caught up with the subway in the 1980s, and the whole thing was a complete mess, as NYCSubway.org explains:
In the first half of the 1980s, service, infrastructure and crime were abysmal. There was no preventative maintenance - components were fixed as they failed - which was often. Breakdowns occurred an average of every 6,200 miles; down from 15,000 in the mid-seventies, also not a figure to be proud of. Signage was very poor, or unreadable due to the graffiti. By early 1981, one quarter of the trains were out of service, and thirty minute commutes ballooned to one and a half hours.1
The trains themselves were covered in graffiti, robberies were common, and there were a large amount of safety issues as well. While the subway now is merely inconvenient and a pain, in the 1980s it was downright dangerous.
Oh, and there was an official policy of placing the least reliable cars on the longest runs of the system. Try and explain that one.
Eventually federal funding was secured and the subway was improved kind of, and fares were raised in order to maintain the system as it was. Nowadays, the New York City Subway seems to be finding money everywhere.
But when the best thing you can say about something is "it's not great, but we're working on it," you know you've got trouble.