From the Oct. 27, 1906 NYT:

LONDON - Thomas Henry Morris has been fined 2£ 10s by a Chester magistrate for squeezing a woman's hand so that her little finger was broken. The woman had lost her husband, and the man had called to offer condolences. It was as he was leaving her that he broke her finger. He put altogether too much muscle into his sympathetic handshake.

EH.net suggests that the fine is equivalent to £179.07 using the retail price index. At today's exchange rate, that would be about $340.