- "This is it, Mike. I've got a lot of heat on me from people I'm in debt to. I need to drum up some money fast."
Jonnie is in debt to King Courtney, leader of the Uptown Yardies, and needs money quickly to stop Courtney sending his men to hound him for the money. An associate, Freddy has been playing him for a fool and has some money, which Mike can take. Mike drives to Freddy's location and confronts him, demanding ten thousand dollars. Freddy states that he only has $1,000 on him right now and will go to get some more. Freddy leaves a briefcase with the thousand dollars in it and the player is given two options. The first is to play it safe by taking the $1,000 and walking away, or the second option is wait for Freddy to get more money. The first option allows Mike to return to the bar quickly and the second leads to Mike killing Freddy and some associates in an ambush. After Mike collects the money, he returns to the bar and finds Jonnie dead. A car speeds off with Mike giving chase, following the car on to Staunton Island.
If Mike takes the briefcase and runs off before Freddy returns, the reward for completing the mission is $1,000. Alternatively, if Mike waits for Freddy to get more money, the reward for completing the mission will be $5,000. Either way, Staunton Island and the mission Race to Run are unlocked by completing the mission.
- For some reason, Mike refers to Jonnie as "bartender" when finding his body.