ceege wrtoe: I think she found out about it before she left him stranded. Something happened to make Jefferson lose his fortune. Regina could be behind it. I think she stranded him in Wonderland as revenge for his role in the plot.
The reason Jefferson lost his fortune was because he lost his wife due to his profession as a realm-jumper. Then to make sure his daughter, Grace, didn’t also lose her father, he literally hung up his hat. Since he no longer could travel to other worlds to acquire items for wealthy patrons like Rumpelstiltskin, he only could support Grace by picking wild mushrooms in the Enchanted Forest. He only agreed to do “one last mission” for Regina in 1×17 because he was financially desperate and wanted to provide a better life for Grace, except then his worst nightmare came true as he ended up stranded in Wonderland.
"That’s how you know you’ve really got a home. When you leave it, there’s this feeling that you can’t shake. You just miss it." Neal Cassidy