Ruby Yubiwa is a fan made alternate of Shizuo Heiwajima. His character and name came from the song "Ruby No Yubiwa" from the Durarara!!x2 Bonus CD VOL.2.
Even though not much is known about Ruby’s personality, his occupation would indicate him being someone much more cold and collected than Shizuo, who is capable of analyzing things around him and concentrate in order to do his job right. He has also been portrait as acting a little clumsy, forgetting the picture of his target in punibuni’s comic. Some also see him as somewhat cruel and sadistic towards his victims, having fun with his job as a hit man and him being portrait with a smirk on his lips as he is about to take down someone.
His song would also indicate him as enjoying his loneliness since it allows him to act as he pleases and lead a careless life, but at the same time shows him as someone who longs to be beside the one he loves.
Ruby wears a striped shirt which is usually white, but sometimes pink, underneath a white suit. His suit’s jacket is always casually open. He wears a necktie which varies in color. His shoes are white. One of his most unique features in comparison to Shizuo Heiwajima’s other alternates, are his pink, brass knuckles. Ruby also smokes and carries a handgun either in hand or partially tucked inside his pants.
Relationships Editpunibuni, posted on tumblr, Ruby is a hit man for the underground organization, Awakusu-kai. He has many interesting stories involving his job which leads to Toudaimoto wanting to spend more time with him.
It is believe that the two met when Shiki sent Ruby to go kill Toudaimoto for unknown reasons. Forgetting to take the picture Shiki had shown him, Ruby got out of the car and began to look for the man without knowing his appearance. Asking around, Ruby was left with no luck in till he eventually talked with Toudaimoto. After finishing telling the raven haired manga artist about the red hat he remembered from the picture, he asked if the other had seen him. Of course, Toudaimoto replied with a smirk saying he was not him but he knew where to find him.
This then leads Toudaimoto to bring Ruby around with him as he collects information from gangs and other very dangerous people on the streets. Which results into Ruby saving him multiple times.
The short comic then ends with the two back at Toudaimoto's house, (after Toudaimoto had found out Ruby was a hit man), writing down various things that Ruby was telling him about his life so far.