Simon

History
Simon (Shimon) is a childhood friend of Erza's, and was part of the group who were attempting to rebuild the R-Tower in the Tower of Paradise Arc.

Tower of Paradise
After eight years pass, he, along with Shou, Wally, and Miriana, appers at a casino where Team Natsu is vacation at. Attacking Gray and Juvia and appearing to kill the former before kidnapping Erza and taking her back to the Tower of Paradise.

After Natsu invade the tower and Erza tell the group her past, he appears non-hostile this time and hug his childhood friend. He then goes on to explain that he realized something was amiss with Gérard long ago but kept silent as not to endanger his friends, but now feels the time is right to confront him, offering his services to the group. He force to split from the other after Shou turns Erza into a card and runs off, coming across Natsu's fight against Fukurou. He tries to help by using his darkness magic but Fukurou being an owl can see in the dark and attacks him, leaving him wounded and forced to watch the rest of the fight from the sidelines. After Fukurou defeat, Simon begs Natsu to rescue Ezra warning him that that Gérard will take advantage of her feeling to defeat her, which is enough to get Natsu involved in the battle between the two.

In the middle of the fight against Gérard, he sacrifices himself so that Erza would not be hit by Gerard's attack; he reveals just before he dies that he loved Erza all along.

Abilities
Darkness Magic: Simon's magic allows him to control the darkness and shadows in and area to turn everything pitch black
 * Yamisetsuna (Instant Darkness): magic that cuts out the lights in any room he in and plunges it into darkness, allowing him and his comrade to attack unseen.

Thought Transmission Magic: With this magic Simon is able to talk to other people through there thoughts and converse over long distances