Sometimes the phrase is embodied in a simile: “as smart as,” or “as tricky as,” or “as shrewd as a Philadelphia lawyer,” or in such form as, “it would take a Philadelphia lawyer to figure that out.”
But always the “Philadelphia lawyer” is an exceptionally astute person and, nowadays, the implication is that he is given to somewhat shady practices.
Originally, however, to be compared to a Philadelphia lawyer was high praise. Prior to 1800 and for some time thereafter the City of Brotherly Love was the most important and the most beautiful city in America.
It held, until 1800, the seat of the new federal government and was the financial center of the country. It was also the center of literature and intellect. Naturally the city attracted the best legal brains of the country, men constantly obliged to sharpen wits against others equally sharp and more than a match for other men with lesser opportunity.
But when wits become too sharp, practices are likely to become less scrupulous, so what had been praise turned to satire as lawyers began to become less honorable.