Both spellings are acceptable, per the dictionary. However, even though I most commonly see it spelled “judgment,” it makes much more sense to spell it “judgement,” based on how it’s supposed to be pronounced.
It definitely appears to be an old strip, and the first frame saying they’re celebrating 101 years may also imply such. They should’ve included the original date.
The punch line should’ve been that he always relished giving good news in person. If he enjoys it, then to him it would be good.