I’ve been speculating for awhile now that one of the heads of the Home Office, if not the current head, was Dorothy. There have been many Oz references his season and I think it makes sense if Dorothy’s time in Oz was more negative.
Well here’s some timeline goodness for you then RG. We know that around the time that Jefferson was getting Frankenstein to help con Regina (who was just becoming the queen so may 10 years pre-curse…) Jefferson was bringing Rumple stuff from Oz because Rumple asked about the slippers but they had already been used by the time he got there….so maybe a late 20s / early 30s at most Dorothy! (Depending on how old they make her when she goes to Oz but still…totally plausible she’s still around and fairly young).