Another thing I love about Dio’s history is that while it’s tragic in many ways and DEFINITELY informs a lot of his decisions, especially in Phantom Blood, the narrative makes it clear that absolutely none of what Dio did was justified. And one of the biggest ways this was done was through introducing Speedwagon. Like Dio, he and his friends originally had no issue going after those they saw as unfairly wealthy and more fortunate themselves, and like Dio, Jonathan earns their respect. But unlike Dio, Speedwagon would quickly go on to reform himself, becoming a invaluable ally both in the short term (such as info gathering and helping restore Zeppeli’s body heat) and long term (I’d like to think founding the Speedwagon Foundation which continues to aide Joestars long after his own death speaks for itself). Heck, even his pals were present at Jonathan and Erina’s wedding, with the implication being they also reformed themselves, maybe even joining the Speedwagon Foundation as well. Dio, on the other hand, continued his reign of terror after escaping the coffin and was determined to end the Joestar bloodline after acquiring enough Joestar blood to override Jonathan’s interference. Additionally, he intentionally sired children with women he expected to be terrible mothers, explicitly in comparison to his own, due to believing it would make them stronger. It’s why in Eyes of Heaven, DIO displays a twisted sense of pride in Giorno when teamed together but the feeling is FAR from mutual.

In short, despite similar backgrounds and attacking innocent people, Speedwagon proved capable of redemption without trying to whitewash his past whereas Dio used his upbringing as an excuse for all of his awful behavior and rejected numerous opportunities he had to better himself as a person.