In the summer of 1892, Jack went on a long cross-country train trip. It was big news. When he hit Richmond, VA that August, the Richmond Times described his appearance as follows:

“When he arrived in Richmond his toilet was simple and cool for traveling as he was attired merely in a tall Cleveland beaver.”

Wait, what?!? Was Railroad Jack, a small terrier, wearing a hat?

Ok, let’s back up for a second. On this extensive road trip, Jack accrued many, many odd gifts. We’re talking human skull level of weird (seriously). One of the less bizarre gifts he received was a “white Cleveland beaver” hat.

People ascribing political affiliations to Railroad Jack and Owney was actually a pretty common occurrence. Legend has it that Jack attended Cleveland’s inauguration, but I’ve never been able to confirm that.

Apparently the hat came with the following notes: “This is not grandfather’s hat. Jack is a good democrat and this is a hat that belonged to a Cleveland democratic club. Hurrah for Grover!” and “I’m Railroad Jack, a Democrat, And always wear a Cleveland hat.”

Again, there’s a reference to Jack “wearing” the hat. Did he really wear a tiny, doggy hat? I don’t know. I want to believe it, but I suspect this is just one more instance of exaggeration that peppered reports of his travels. But, since we don’t know for sure, let’s just all keep imagining a little hat perched atop his scraggly head. It’s funnier that way.