Milton Bobbit was a member of The Blacklist who performed contract killings by proxy.
Fifteen years ago, Bobbit was part of a rigged drug trial for a treatment for Type 2 diabetes. Unfortunately, the drug was highly defective and only made his condition worse. Once he realized that he was dying, he lost all fear of death, but started self-medicating on all manner of pharmaceuticals and alternative treatments, some of it involving fungi he grew in his home. Realizing that many other people suffered when their insurance company increased their rates due to a terminal illness, he offered these people enough money to give their families financial security in exchange for killing someone as part of a contract killing, using his day job at an insurance company to find potential killers. To make sure the seemingly random deaths looked more like accidents, he usually picked assassins whose illnesses also caused mental problems. A crucial condition of the agreements was that the assassin would kill themselves along with the victim to avoid leaving a witness for the police. In the criminal world, Bobbit came to be known as "The Undertaker".
Realizing that his illness was going to kill him soon, he began selling assassinations to kill the people involved in the rigged drug trials.
- Nasim Bakhash and Milton Bobbit operated in the same way. They worked as contract killers until they saved enough money to fulfill their personal contracts. In both cases Reddington was interested in their client list.
- Rebecca Thrall and Milton Bobbit used a variation of the same scheme.
- Milton Bobbit
- Rebecca Thrall
- Targeted the terminally ill so the corporation could collect on the corporate-owned life insurance.
- Paid the police officer in a loan that is not repaid.
- The mental illness explains the reason for the justified police shooting.
- The case is closed as the assassin can use the law to their advantage.
- The contractor secretly undermines the accuser and protects the assassin.