Montgomery has been a Deadpool supporting cast member since the early issues of Deadpool's '97 series. Montgomery's (Monty's) precognitive abilities where the reason for the entire Mithras Directive and contributed to the cataclysmic events of the Deadpool story arc Dead Reckoning. At one point in his service at Landau, Luckman, and Lake Deadpool kidnapped Monty and took him to a Monte Carlo casino. Deadpool implored (threatened) Monty to use his precognitive abilities to win Deadpool money at a number of casino games. After Deadpool rashly made a large bet of 2,000,000 dollars with a gaudy Frenchman Monty initially refused to help him. But that gaudy Frenchman insulted Monty and as vengeance Monty helped Deadpool win the bet.

Back up in their hotel sweet Deadpool was doing swan dives into his money as the door is kicked in and it is revealed that that gaudy Frenchman was Batroc the Leaper. He wanted his money back. Fighting ensued. Deadpool wins and gets in another argument with Monty. Monty complains about never being surprised. He always knows whats going to happen. As a solution to this problem, the ever rash Deadpool throws Monty out of the window of the high-rise hotel. Monty at the bottom, in a swimming pool, is overjoyed. He exclaims that he is so excited that there was a 6% chance of him living through that ordeal and he had no idea whether he was going to live or die. He thanks Deadpool and the exit via teleportation door to return Monty to L-L&L.

Soon after returning Overboss Dixon, of the Mithras Directive mind wipes this eye-opening ordeal from Monty's brain.

The Mithras Directive goes into full effects thanks to Monty's pre-cog powers. After the events of the Mithras Directive Deadpool takes Monty (who at this point has been decommission from LL&L for "unauthorized emotions") to his new and very secluded home.

Monty remained there and enthusiastically aided Deadpool on several missions before the return of T-Ray. To let Deadpool know that he had returned T-Ray beat Monty to within an inch of his life and sent his body to Deadpool.

Deadpool, not knowing where else to go, took Monty's body to LL&L where Zoe Culloden had taken over as Overboss after Dixon's death. Zoe eventually revives Monty. The two realize their love for each other. Zoe resigns rather rebelliously and the two go into hiding through a teleportation door. Monty sincerely bids Deadpool farewell.

He is presumed happy wherever he is with Zoe.