I think he may have but could he have lived on the street?
If he did he was already in a dreadful state and more gore on him might not have been noticeable. People who live on the street usually have some sort of bags or a way to keep what little belongings they have, a perfect way to hide a knife, and any thing else.
Thats one aspect of the more entrenched views about Jack that I question a lot....why would this man have to be poor and homeless? What in the evidence suggests that the man had no means or no place to call his own?
I suppose its the locations of the murders.....in a ghetto, and the feeling that the man must have lived in that ghetto to know it so well.
The truth is that he may well have been a toff for all we know, and could have lived 10 minute walk or more from the Whitechapel/Spitalfield killing ground.
In fact one might suppose that one of the reasons that he was never caught leaving a crime scene is because he immediately left that specific area afterward. Its one thing to imagine him weaving in and out of alleys dodging patrols, by passing potential witnesses....then slipping back into his lodging house and plunking the organs in a tankard by his bed....and quite another to have him slip off his gloves, place a hanky wrapped package in his coat pocket and stroll away into the night.
But either could be possible based on what we see in the evidence.