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CheckOut is a Checkmate/Outsiders crossover written by Greg Rucka and Judd Winick, with illustrations by Eddy Barrows, Joe Bennett, Matthew Clark, and Ron Randall. It takes place in the Checkmate series between Corvalho and Fall of the Wall, and in the Outsiders series between Pay as You Go and Five of a Kind.
Checkmate begins capturing the Outsiders. Mademoiselle Marie seduces Captain Boomerang. Tommy Jagger surprise attacks Katana. Count Vertigo knocks out Metamorpho. Fire leads a team to take down Grace and Thunder. Nightwing breaks into The Castle and demands that Sasha Bordeaux explain why she's targeting his team. Sasha breaks out of Nightwing's grip, and Nightwing decides to break his friends out. Nightwing releases Grace, and they bust holes through the building to find the others. They're stopped by a tactical squad and taken to the conference room, where Checkmate and the Outsiders are meeting. The U.N. security council told Checkmate to shut down the Outsiders, but Checkmate intends to use them as a covert strike force. Bordeaux explains that the Science Squad is still active on Oolong Island, but the government cannot intervene without angering North Korea. They fly to Oolong in the Pequod, where they're immediately attacked by a giant monster.
Grace and Thunder defeat the monster. They land on Oolong and split up into teams. The infiltration team is Captain Boomerang, Mademoiselle Marie, Nightwing, and Sasha Bordeaux. Fire, Grace, Thunder, and Tommy Jagger are assigned to support. Count Vertigo, Katana, and Metamorpho are assigned to exfiltration. Boomerang lets it slip to Bordeaux that he did work for Amanda Waller in the last year. Vertigo reports this to Waller and King Faraday, who realize they must sabotage the mission or risk facing charges. The infiltration team breaks into the facility. They connect to the datahub and a computer virus is sent back to Checkmate. Mister Terrific is forced to disable their computers, leaving the infiltration team stranded with alarms going off. Oolong Island is overwhelmed with security robots. The infiltration team uses an EMP to survive the facility. Mademoiselle Marie escapes with the information they need on a T-Sphere. Boomerang, Bordeaux, and Nightwing are captured. Katana pilots everyone else off the island, where they're attacked by Immortal Man in Darkness of the Great Ten. It's revealed that Chang Tzu is still in charge of Oolong, and he's working with August General in Iron.
Chang Tzu does painful experiments on Boomerang and Bordeaux to understand the nature of their powers. This includes cutting off Bordeaux's arm. Ambassador Shi of China gives Checkmate permission to do a rescue mission without Chinese interference. Immortal Man in Darkness gives air support while they return to Oolong. Mister Terrific tells Amanda Waller that he knows about Task Force X. It's revealed that Chang Tzu has left the island, and he's now in North Korea. Checkmate cannot intervene in North Korea, but Batman arrives to volunteer his services. Mister Terrific and Waller cancel the Outsiders' deputization so they can deny responsibility. Checkmate's Knights and the Outsiders battle Chang Tzu's robots to create a diversion for Batman. Boomerang and Nightwing break out of their cells, and find Batman already there. Chang Tzu has escaped, leaving Sasha behind. Batman takes Sasha in his arms and carries her to safety. She asks that he does not look at her in this state, and he tells her things will be all right. In the aftermath, Nightwing tells Batman that he does not want to lead the Outsiders anymore after this. Nightwing suggests that Batman take control of the team again, and Batman says "maybe."