This is a real long-shot, but it turns out that George Cutshaw, a decent major leaguer and an Obak card subject, played for the Bloomington Bloomers in 1908 and 1909. Anybody have a nice head shot of him? Another big leaguer, Les Nunamaker, played for them in 1910. Fred Beck, who has his very own T205 and T206, was a Bloomer from 1905 to 1908.
There's a wonderful website about the Illinois-Indiana-Iowa League at
www.three-eye.com. And for what's worth, there's a rural community called "Kentland" in Illinois.
By the way, that's a great-looking photo ...