Check Mate
For: Billy Grey
Location: Chase Point, Bohan
Target: Oliver Pegorino
Conditions of mission failure: Player or Billy is killed
Reward: 10000$
Unlocks: Tough Times
Unlocked by: Log Out, Make Your Move
Check Mate is the twenty second story mission in GTA: Playboy Life given to protagonist Playboy X by The Lost MC President Billy Grey.


Playboy meets Billy Grey and the Lost MC at the bridge construction site in Chase Point, Bohan. Oliver Pegorino is there, having a meeting with the Angels of Death. Playboy and Billy have arranged to work together and take down the AoD and Oliver in order to prevent his plan of hiring the bikers to kill his father, Jimmy Pegorino, from succeeding.

Billy's men attack the Angels of Death members, while he and Playboy proceed towards Oliver, killing the body guards on the way. They catch up with Oliver on top of the unfinished bridge. Oliver curses Playboy and Lugiano Lupisella for putting their noses in his business, before he's shot in the knee by Playboy. Oliver lose his balance and falls down into a ferry full of explosives. Such an infelicitous end.

Playboy thanks Billy, who then rides into the night with the rest of the Lost. Playboy calls Lugiano, and informs him of Oliver's demise. Lugiano thinks Jimmy Pegorino won't believe his own son plotted to kill him, so Lugiano decides to tell him Oliver commited suicide.


  • Follow Billy
  • Take down Oliver's Body Guards
  • Chase Oliver 
  • Take down Oliver Pegorino
  • Escape the collapsing bridge

Gold Medal Objectives

  • Time - Complete in 5:00
  • Accuracy - Finish with an accuracy of at least 70%
  • Headshots - Kill 10 Enemies via Headshot


The reward for completing is 10 000$.

Post Mission Phone Calls

Playboy: Lugiano, Oliver is dead, Jimmy and your truce with him are safe. Lugiano: So, how did it go? Playboy: Well, the building of that bridge is going to have to start over.. No witnesses. Lugiano: Pegorino ain't never gonna believe his own son tried to kill him.. We'll gonna call it suicide. Playboy: That was one showy suicide. All those explosions and shit. Lugiano: Hm.. I'm gonna leave the explosions out of it. I'll inform Jimmy about his loss. Goodbye, Kid.

Dwayne: Trey, son.. I need you now. More than ever.. Playboy: D-Dwayne..? Everything alrig... Dwayne: OF COURSE NOT! It's Jayvon.. That little shithead slithering snake.. GOD DAMN. Trey, Playboy, what ever the hell your name is.. GET HERE NOW!


  • This is one of the missions where you are able to get one of the Golden Weapons. A Golden Scorpion is in the closet of Oliver's hideout.

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