Here is the final artwork for a little bit of leisure time in the Enterprise Lounge.
If Captain Kirk spent time in the lounge, he was often in the company of his first officer, Mr. Spock, and they would play chess. Yeoman Rand spent quite a bit of time close to the Captain as well, so I thought it would not be too far of a stretch to depict them playing cards. The game they are playing is the inspiration for this artwork, but I will talk about that in another JSVB post in the future.
Before she "transferred off the ship", the Yeoman Rand character was planned as the lead female for the original Star Trek series. Just as Janice Rand was universally liked on the Enterprise, Grace Lee Whitney, the actor that played Rand, was reported to be well regarded on the Star Trek set. Even so, many dark rumours surround the early departure of Whitney from the series, including abuse and alcoholism.
It's my thought that Kirk and Rand could share a bottle of Saurian Brandy responsibly over a friendly game of cards, so that's what I drew.