What the data shows

Jev's ratings have essentially nothing to do with the voters'. The rank correlation is 0.02 across all captions and a median of 0.03 inside a contest, where the comparison is fairest.
- Picking the winner: Jev's top caption is the voters' top caption in 10% of 218 contests (those with 5 or more captions). Picking at random would get about 8%.
- Everything is "somewhat funny": Jev puts 86% of captions in the middle. The voters' most common verdict is "unfunny" for 99% of captions: a tough crowd meets a polite judge.
- Order doesn't explain it: with the answers reversed the correlation is 0.01.
What it means, and what it doesn't
Ask Jev which of your captions is funniest and you'll get something close to a coin toss, delivered warmly. Its middle-of-the-road "somewhat funny" isn't a verdict about the caption; it's the answer it gives almost everything.
It doesn't mean Jev has no sense of humor at all. On classic jokes whose reception is well known it agrees with crowds closely (see "Old jokes yes, new captions no"). New captions have no reputation to lean on, and the joke often lives in a drawing Jev never saw.