Well, how do you want to capture him?
This will put it at the beginning of all the relevant lines:
:%s/^-\+\%(\s-\+\)*\s\?$/\=strlen(submatch(0)) . ': '. submatch(0)
\=allows you to substitute the result of a vimscript expression for the corresponding string.
submatch(0)matches the string ( submatch(n)will be the nth group).
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