Regardless of any break-up situation, there are always second thoughts; it isn’t easy to break off a meaningful relationship. In fact, feelings, sentiments, emotions tend to last years after the end of a relationship.

This idea is mirrored in the music. As Paul says “stop”, the music does so, and the intensity of his singing indicates assertiveness; he’s made a decision. Then the music comes back as he second-guesses himself, with a “well, maybe…” kind of attitude.

Mr. Leitch is the tailor that Paul Simon was in a previous life. This is a reference to the singer Donovan, whose last name is Leitch, and was suggested by the woman who says these lines, since she was friends with him:

As for Leitch, the girl who said that on the record, her name was Beverly Martyn (…) I knew her from way back in English scufflin' days, and we brought her over to sing at the Monterey Pop Festival. (…) And she was friendly with Donovan. So, we decided to make up this little vignette about the shop – we wanted to come up with a name. She said, well, let’s put in Donovan’s name.

Like the previous “dubious soul” line, he’s again speculating as to the source of his lack of confidence in his actions. Similar to a tailor who is fashioning clothes according the the client’s exact specifications, he is directed by the wishes and whims of others in social settings — that is, reacting and responding rather than interacting fully.

The idea of Paul Simon being a tailor came from his wondering what he would have worked as in the past:

During some hashish reverie I was thinking to myself, “I’m really in a weird position. I earn my living by writing songs and singing songs. It’s only today that this could happen. If I were born a hundred years ago I wouldn’t even be in this country. I’d probably be in Vienna or wherever my ancestors came from – Hungary – and I wouldn’t be a guitarist-songwriter. There were none. So what would I be?

“First of all,” I said, “I surely was a sailor.” Then I said, “Nah, I wouldn’t have been a sailor. Well, what would a Jewish guy be? A tailor.” That’s what it was. I would have been a tailor. And then I started to see myself as like, a perfect little tailor.

Then, once talking to my father about my grandfather, whom I never knew – he died when my father was young – I found out that his name was Paul Simon, and I found out that he was a tailor in Vienna. It wiped me out that that happened. It’s amazing, isn’t it? He was a tailor that came from Vienna.