OOTP used to do Jr. for fictional players, then sometimes you'd see Jr. Jr. which obviously was a bug, but no longer. Now just fictional Jrs happen at times.
I often create generational players for my leagues, and when they go on for 100s of seasons, it's not odd to see III, IV, V players from time to time.
I had one series of families where the greatest player of all-time had so many legacies that another family name (via his great granddaughter) spun their own dynasty. It's a lot of fun for me and a good way to remember certain players.
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