Nothing is known of Grady's background. However, it is revealed in the mission "On Shaky's Ground" that he has some involvement in criminal activities. Grady has a relative, Clinton Underwood, buried in Blackwater cemetery.
Grady plays a minor role in the mission "On Shaky's Ground", in which he is seen as one of the bandits interrogating Shaky. After John Marston breaks into the warehouse, Grady can be shot dead or hogtied.
Grady can usually be encountered in Blackwater and Manzanita Post, where he rides horses, or does a variety of odd jobs. However, he has been known to frequent multiple locations throughout West Elizabeth and New Austin.
- If the player decides to kill Grady in the mission "On Shaky's Ground", Grady can still be seen in his usual locations afterwards.
- Grady shares a character head with Roy Twaddle, Jeb Murphy, Coke Buckley, Tobias Finkelstein, Gus McCallum, and Virgil Scoggins.
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