Caleb Keireiji

Caleb Keireiji (敬礼寺 ケイレブ) is a Japanese gangster. While initially appearing as a well-connected bar patron, Keireiji is later revealed to be the boss of the Caleb Family.

Background
During the war, Keireiji worked as a drill instructor.

After the war, Keireiji took up a position as managing dock workers and used his money and charisma to clandestinely build a force of ex-soldiers who work under him. He views it as his responsibility to save the postwar Japanese from their oppressed lifestyle and believes he can fulfill this by gaining exclusivity rights over his district and eliminating the outsourcing of labor.

Personality
Keireiji suffers from severe PTSD due to his time in World War II, leading to recurring nightmares. He spends nights walking through town, leaving cigarettes in place of incense as a form of memento for the dead.

Season 1
Caleb first appears as a bar patron who meets Leo Shishigami at Nobushi. The two become friends and Caleb helps Leo find a missing American lieutenant. Soon afterwards, he helps Leo find and eliminate Alfred Akagi.

After this point, Caleb reveals his position as boss of the Caleb Family, a crime family who were at odds with Alfred. Caleb takes complete control of District 23 and takes money from several smaller mafia groups and businesses. He attempts to coerce money from Primavera, however Rose Haibara refuses, leading Caleb to kidnap her. Rose is then tortured by Miguel Kurashiki and is released shortly afterwards.

Caleb attends a meeting with Philip Butler and attempts to negotiate for complete ownership of the exclusivity rights to District 23; Butler requests a one-hundred-million dollar payment. Caleb manages to come up with this money by coercing more businesses under his control and taking over Primavera with his lover, Amanda Amamiya.

Rose orchestrates a plan to assassinate Caleb with the help of Philip Butler and Meijiu Lee, which culminates in the Night of Roses and Guns. The plan succeeds and Caleb is seemingly killed.