For some, Super Bowl media day can be even more exciting than the game itself, as athletes preparing for the biggest moment of their lives are forced into interacting with a whole cast of characters from the media. Characters including Guillermo the security guard from Jimmy Kimmel Live.

This year Guillermo one-upped himself, managing to not only have an intensely awkward moment with Bill Belichick, but also one with Tom Brady.

 Getting Bill Belichick to smile on command is surely an achievement that is more than worthy of being awarded a Super Bowl ring, no?