/\ I'd question those stories.
Don't forget, Jigga was in Big L's shadow for most of the 90's. Listen to "Da Graveyard" off Big L's first LP and it's obvious who the star is.
Then listen to L completely kill of Jigga on the 7-minute freestyle - Jigga tried to drop his early trademark double time flow, Big L did the same and shit on him "Ay yo my crew be delivering high lead when gats are clenched/rappers I jack and lynch/nobody can cope with the way I be killin that shit at rap events/Big L is that nigga you expect/to catch wreck on any cassette deck/I'm so ahead of my time my parents haven't met yet"
Jay had no swagger at this stage in his career, you can hear it in his voice, he was a rookie. And this was like '94/'95. If Jigga was that much of a don on the streets, he would have had way more swagger than that. There's almost a nervousness in his voice.
I'd give you '96, after Reasonable Doubt and after he started rolling with Big, because Big rolled with them dudes. The whole of Bad Boy was running with them flashy ass hood gangsters at the time and had been for a while. Not to mention due to Jay creating Roc-A-Fella with Dame and inking the Priority distribution deal, Reasonable Doubt, although not a massively high selling album at the time, earned Jigga a lot more scrilla than Average Joe Rapper on a major label. So he had his own scrilla by then........for the sake of a good story rumors may have been spread that he had been living that life a couple years prior...etc.