|“|| Kill... me...
Leonard Cosgrove is one of three playable character in NightCry and is the teacher of both Monica Flores and Rooney Simpson, as well as Rooney's distant relative. In this sense, he is the closest thing to a father figure Rooney has. Leonard is only playable in Scenario 2.
Leonard is a British-born cultural anthropologist, and is escorting the heroines and her friends aboard the Oceanus cruise. He's hands-on, logical, and interested in occult phenomenon from an anthropologist's point of view, but has managed to get to the bottom of and debunk several occult deceptions.
In his heart of hearts, he is actually a single romantic and occult fanatic. He wants nothing more than to one day encounter an honest-to-goodness supernatural phenomenon that he’s unable to demystify.
Leonard is only playable in Scenario 2.
Due to the events of Scenario 1, Leonard attempted to find help, but his phone was unable to get a signal. To make matters worse, he also discovered that all of the life rafts were missing, implying that at least some of the crew members had in fact been involved in perpetrating the massacre. He, Eric and Cobie eventually found an emergency inflatable life raft and used it to head over to a nearby island.
Upon arriving on shore, Leonard volunteered to go out and investigate the island. He then uncovered the existence of a mass-murdering cult, as well as the fact that one of the high-ranking members had a false eye, also sending a text to his students warning them of this development. Later, he found a secret chamber, where he found Jerome Theuriau, who was abducted and tortured, and learned that the Oceanus was going to be the site for an arcane ritual.
When he returned to the beach carrying Jerome on his back, he, Eric and Cobie proceeded to try and hurry back to the ship. Unfortunately, when they returned to the ship, an explosion went off from the inside the ship. Leonard looked towards the source of it in shock and quickly turned around to tell the men to hurry up, but was caught off-guard by an unknown Faithful member. However, it is implied that this member is Eric or Cobie (most likely Eric), since Jerome is shirtless and the member appears to be wearing a crew uniform.
Leonard briefly appears in the beginning of Scenario 3, where he attempts to encourage Rooney to be more sociable during the party. He is also referenced by Maria Ortiz, where she expressed concern due to his disappearing after calling him.
After this, the events of Scenario 2 begin, and Leonard is flayed by the Faithful.
Rooney later finds him in a tub of liquid in the infirmary room and discovers that his body had been flayed from the neck down. He has been kept alive, but is trapped in agonizing pain, to the extent that he can only beg for death. Rooney ultimately heeds his request by shutting off his life support machine and euthanizing him. Connie appears, amused by the fact that Rooney is killing again just like how Rooney once killed Connie. When Rooney walks away, Connie tries to guilt trip Rooney into leaving so soon, since Leonard was a father figure to Rooney. Rooney orders to shut up, tells Connie the truth of her death, says she is going to continue with her life, and leaves.
- It's all too late: (Chapter Two) When Leonard enters the well, he falls to the bottom and is promptly killed by the Scissorwalker. A week later, a newscast reports how everybody on the Oceanus disappeared and that there are no clues to this mystery.
- Seduced by the snake: (Chapter Three) Rooney refuses to turn off the life-support machine and leaves the room. While she crosses the partially destroyed corridor, she hears Leonard calling out to her. Leonard's head floats past her, lamenting about being trapped between life and death and mumbles, "It's the curse of being killed by...". He is thrust out of the water before he could continue. Later, Rooney enters the staff elevator, only to see something slithering around her. Leonard's head suddenly pops into view. Soon after, he is seen reduced to just a head with a spine and coiled around Rooney, telling her they will be together forever.
- Leonard shares many traits with Professor Samuel Barton from Clock Tower.
- Leonard is the only playable character to never encounter Scissorwalker during standard gameplay. However, failure to complete certain objectives will result in Scissorwalker ambushing and killing Leonard in a cutscene when he fell to the bottom of the well.