"Boss" from Roper Bros. Inc.

Boss citrus crate labelMeet the Boss. He's an imaginary character who ran the Roper Brothers citrus groves and cattle ranches. This image was probably created around 1930 and harks back to the field boss with the grueling job of running operations in the sweltering Florida sun. It’s safe to say people probably didn't mess with him.  

The Roper family settled in Florida in 1857. Sidney Emmett Roper, the family patriarch, was the first Orange County school superintendent and a grocer. Back in those days, if customers didn't have the cash to pay their grocery bill, they'd commonly offer land in exchange. Sidney started in this fashion to build his citrus empire, since much of the land he traded for came with orange trees already growing on it.
 Roper brand label
Roper Brothers was formed in 1920 by Bert, Fred, and Frank Roper. Before long, the family would say that the only piece of land Frank wanted was the piece of land next to his. 

Today Charlie Roper, Sidney’s great, great, great-grandson, runs Roper Brothers. The family still grows citrus on 1,400 ares of land in Winter Garden and surrounding areas and has expanded to producing a number of other crops.

Boss was just one of many colorful citrus crate labels created by Roper Brothers. Sometimes they brought the influence of the cattle ranch over to the labels of their fruit operation, since the Roper family name fit nicely with the lassoes they used on the ranch.

Though decades have passed since the Boss graced the labels of Roper Brothers citrus, he still remains the figurative head of the shop. Coincidentally, Charlie says the Boss image bears a strong resemblance to his dad, though his father wasn't quite as stern.

Good thing. The guy in the picture may have been good at running the field. He doesn't look like Father of the Year.