Do you Mean What you Say?

Thanks to Usual John for sending this in, and for useful email discussion! His focus is on the bottom strip, where we get amusing literalized visions of some common idiomatic expressions. Except — we apparently no longer have an idiom to match “He had a pony on his cuff”. So, what would that mean, apart from what’s in the literal illustration?

By the way, can anyone assist my memory and give me a clue why I remembered this Origins of the Sunday Comics feature as not always in the past being a genuine historical exploration, but rather including sometimes a parodic or fictive-history take? Maybe mental contamination from reading a sometime series of posts in Working Daze, pretending to trace a century-long history of that strip, thru different writers and artists, and even titles and publishers.