I lied about not focusing on ducks, have some more Duck Thoughts.
Scrooge is the richest dude in all of the Radiant Garden and Twilight Town area, and tends to have a chauffeur drive him between the two and around RG. But he'll ride public transit if:
It's a free ride day. He's cheap as hell; he simply can't resist.
Gas is more expensive than usual
The triplets want to take the train/tram for fun, because Scrooge is a huge softie actually
All this to say, Scrooge and Cloud have ended up in the same train compartment a few times. Sometimes Scrooge rants about things in the business section of the newspaper to anyone within earshot. When he looks around for validation, Cloud just nods awkwardly because his mamma taught him to respect his elders, even though he frankly has no idea what's going on.
Cloud is the first Strife to meet Scrooge actually, since he lived in Radiant Garden before the rest of his family moved to Twilight Town. One night on the phone he's telling the twins stories of the interesting people he sees on the train, and the twins DEMAND proof of his claim that there's sometimes a man who wears an honest to god top hat. They tell him to take a photo next time, but Cloud retorts, "I'm not carrying around a camera just to take sneak shots of strangers."
"Your phone has a camera."
Another time on the train, Cloud finds himself in the company of an exhausted looking man and a pair of rambunctious, identical young boys. The kids run around the train car, climbing on seats to look out the windows, and chattering nonstop to anyone who makes eye contact. The tired man tries to rein them in, apologizing to Cloud, who happens to be sitting closest to him. Recalling his own single mother struggling to wrangle him and his brothers at that age, Cloud tells him not to worry about it. As the boys start a tug of war over something, Cloud adds, "My little brothers are twins too."
That's when a third identical boy pops out of the overhead rack and chirps, "Actually we're triplets!!"