By default, newsyslogd inserts a timestamp into a file after the log has been rotated - the new file receives the timestamp. Since emacs expects savehist files to be formatted correctly as elisp, this leads to the error I saw on startup.

The fix for this is to modify the newsyslogd command to use the “B” flag. For example:

# logfilename [owner:group] mode count size when flags [/pid_file] [sig_num]
/Users/username/.emacs.d/.cache/savehist username: 644 5 * $W0 JB