Hmm, it looks like the Caddy web server got $50,000 at one point (in 2016 apparently). They were the ones who recently decided (in mid 2017) that it was a good idea to add HTTP headers advertising the names of their sponsors to their open source version. Then, when someone forked their project, they filed a GitHub issue one hour later accusing the fork of trademark infringement! See the discussion here:

https://news.ycombinator.com/item?id=15237923

As to this year's MOSS recipients, Ushahidi received almost $200,000. They're a Kenya-based startup that was the darling of the Nairobi tech scene a few years ago but have increasingly come under criticism for their leadership during a recent sexual harassment scandal:

https://qz.com/1026890/kenyas-ushahidi-is-investigating-sexu...

Furthermore, one of their affiliated startups, who was making a "rugged" router powered by OpenWRT, was violating the GPL and was being quite dismissive and condescending to those of us who pointed out that they should be releasing the source code of their product. I covered this on my personal blog at the time:

https://mjanja.ch/2015/05/brck-in-violation-of-the-gpl/