I drew both of these almost twenty years ago around the same time that Generations
was in theaters. Captain Greene is my fanfic captain of a Galaxy-class starship and a contemporary of Picard, Sisko and Janeway, but many of his details have changed since I drew this picture (most notably that he doesn't die in 2372) and as I slowly refined the characters in my stories and firmed up who they are and where they come from. In my stories he no longer has such a decidedely Shatnerseque appearance or hair.
The "#29 of 31" at the top of Greene's picture is because he was meant to be one of a whole series of pictures I would draw of my fanfic crew, their ship and alien adversaries, but I never drew more than a few before dropping the idea of numbering them like collector/trading cards.
I did kind of like the idea of a late 24th century trading card company that would print cards featuring famous starship commanders, explorers and other luminaries of the era. You know, for the kids of all different Federation species.