Tom Reagan serves as the right-hand man to mob boss Leo O'Bannon. He secretly sleeps with Leo's girlfriend, Verna, and pressures Leo to sacrifice Verna's brother, Bernie, to rival Johnny Caspar. After being publicly beaten and cast out by Leo, Tom allies with Caspar but fakes Bernie's execution. He manipulates internal gang tensions, orchestrates the deaths of Caspar and Bernie, and ultimately refuses Leo's offer to return to his position.
Tom is Leo's chief adviser and organizational lieutenant.
Tom serves as Leo's right-hand man and advises him during the conflict with Johnny Caspar.
Their affair destabilizes Tom's loyalty to Leo and contributes to his expulsion.
Verna secretly sleeps with Tom behind Leo's back.
Tom is ordered to kill Bernie but initially chooses deception and mercy.
Tom leads Bernie to Miller's Crossing for execution but fires into the ground and lets him escape.
Caspar temporarily recruits Tom into his organization.
After Leo casts Tom out, Tom turns to Caspar, who gives him the loyalty test of killing Bernie.
The Dane repeatedly tests Tom and threatens to expose his deception.
The Dane suspects Tom's loyalty and takes him back to Miller's Crossing to verify Bernie's supposed death.
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