When Jag first went to the Humane Society, his name was Max. THEY changed it because they had just had a Max recently and didn't want to get all mixed up (that and he just is NOT a Max). They changed it to Jag because whenever they let him out of his 'kennel' (the bathroom) or let him out in the yard, he was just "jag" around. So they named him Jag. I wanted to change it, but the whole family couldn't agree on anything, so we just kept Jag.
Every name I could come up for Chester just did NOT suite him. My brother saw him, and immediately said "Chester. Or Charles, but I like Chester better." I looked at him, and said, "You're right. He's a Chester." He got the inspiration from Chester the Pug (you can look him up on YouTube. His 'dad' does a whole huge series on him and Charles, his two pugs, and writes/makes/records his own music for it. They're a huge hit, and absolutely adorable). Chester is just so incredibly goofy that he needed a goofy name. I had been calling him "Baby" all day for lack of a better term, and it seemed to calm him down.