Uncle Sam's image was frequently used on cigar box labels "Often seen with cigars spread across the globe, it cemented the idea of a ‘Prosperous Nation’ in the subconscious of Americans." (https://cigarlabelblog.wordpress.com/2010/06, accessed December 19, 2014). In this case, it's certainly possible to view the image as the U.S. exporting its unwanted cigars - particularly with an apparent smirk on Uncle Sam's face.
The date is estimated.