|The following is based on Van Buren and has not been confirmed by canon sources.|
There are two ways to obtain this epithet. The Prisoner can try to convince Bear that Kyle needs to be replaced, thus no longer giving Kyle control over his fate, or, the Prisoner can reveal Presper's true plans of cleansing the wasteland with nuclear fire to General Coleridge and his men.
Beyond fuelling Bear's yearning for freedom there are no effects by obtaining it this way. Revealing Presper's plans, however, will cause strife among the NCR soldiers serving him presumably resulting in hesitation to attack the Prisoner.