Conrad O'Shea made a bet with Tombstone on the outcome of a basketball game. Shantee Williams, the star player had an altercation with Deadpool and decided to pull a gun. This resulted in a trip to the emergency room and some expensive surgery to reattach his fingers. As a result Conrad lost the bet. As it turns out it was a very large bet.
For reasons that have not been fully explained, Tombstone has agreed to a double-or-nothing bet with Conrad. Tombstone frames Deadpool for an act of terrorism and then sits back to see if Deadpool can survive the next 24 hours.
This proves to be an exciting time for our favorite mercenary as he is hunted by the Punisher. Spider-Man appears and tries to bring in 'Pool as well. Daredevil convinces both heroes that Deadpool is innocent and eventually learns of Tombstone's involvement.
At the end of last issue, Deadpool and Spider-Man were following Tombstone. They learn too late that it's a trap as he reveals some hired help: The Wrecking Crew.
The Wrecking Crew (Wrecker, Thunderball, Piledriver, and Bulldozer) square off against their targets. They recognize Spider-Man but have to ask about his girlfriend in matching tights. Deadpool introduces himself begins singing the first verse of The Joker substituting his name for "space cowboy".
With the formalities out of the way, The Crew attack. Wrecker catches Spider-Man in mid-leap and sends him airborne courtesy of his enchanted crowbar (the correct name, I swear). Deadpool becomes engrossed watching Spider-Man fly the unfriendly skies and gets a spinal tap courtesy of Bulldozer. At this point The Crew doesn't let up and deliver a massive beating. After all they are getting paid to do this.
At this point Spider-Man returns to Earth. When Piledriver is ready to put an end to Deadpool, Spidey saves his new friend. They stand back-to-back as the Wrecking Crew circles them again. Deadpool comments that this situation feels like Lethal Weapon. Spider-Man asks if he means the first one or the sequel. Deadpool is unaware a sequel was made. He does catch the Wrecking Crew's reference to The Warriors when Wrecker instructs his teammates to "make it rain".
Before they can make good on their threat, an unidentified accomplice knocks out Piledriver and Bulldozer with energy-based weapons. When the smoke clears their savior turns out to be the Punisher on a stolen goblin glider wearing the Unicorn's battle ram and Klaw's sound-generating prosthetic hand. It's so ridiculous that Deadpool asks Spider-Man to verify that what he's seeing is real and not "Pool-O-Vision". His other voices chide him for telling everyone about "Pool-O-Vision".
The Punisher then proceeds to take out Wrecker and Thunderball with pumpkin bombs that contain a powerful incapacitating agent that can stop a herd of elephants. They may be strong enough to take on Thor, but they have to breathe. Deadpool applauds the Punisher for his choice, calling it "Very Steve Ditko". When Spider-Man asks what he means by that, Deadpool just winks to the audience. Once Wrecker and Thunderball are unconscious, Deadpool encourages Punisher to pee on him. He knows Castle wants to. Spider-Man takes a firm stance against this action.
Tombstone and Conrad make their way to his private helicopter. Conrad eventually stands up to Tombstone, stating that he lost the bet. If he won't honor their arrangement, then just kill him and get it over with. He no longer cares. When Tombstone sees Deadpool approaching quickly, he throws Conrad in with his pet boars to cover his escape. Deadpool saves Conrad from being eaten alive but it costs him his right hand. Conrad quickly returns the favor when Deadpool is unable to defend himself. He quickly explains the bet they had. He bet Tombstone that he couldn't take out Deadpool.
As Tombstone prepares to board his helicopter, Deadpool taunts him by calling him a gangsta wannabe. Tombstone's ego will not allow this to go unpunished and decides to win the bet by getting personally involved. This proves to be a poor choice as Deadpool eventually gains the advantage. Deadpool grabs Tombstone and threatens to drive his bony stump through his eye (the one vulnerable part) into his brain unless he confesses. Tombstone reluctantly agrees and is taken into police custody.
When he returns Conrad to his father, his father pays him the money he is owed and then instructs Deadpool to turn Conrad over to the police. He has grown tired of bailing his son out of the trouble he causes and thinks he should face the consequences. Conrad is shocked. Deadpool is happy he got paid.
Later he buys Outlaw a new apartment and furnishes it to make up for destroying her old one. He admits that he doesn't have many friends and she helped him out when he needed it. She is overcome with emotions and decide to reward Deadpool by testing out the new bed he bought for her.
Yeah I was shocked at the ending too. Deadpool normally doesn't get to hook up with hot women. I will admit I was caught off-guard when she went from being "just friends" with Deadpool to "friends with privileges". Apparently she really liked her new furniture. There was some romantic tension between them in issue #2, so it's not completely out of left field.
We have a Deadpool/Spider-Man team-up that you can believe in, provided you ignore their first meeing in Cable & Deadpool #24. In this issue, Deadpool (accidentally) throws Peter off a bridge (it was a moving car going OVER a bridge). Not that he would tell Deadpool this, but it wasn't even referenced. Not sure if that is a good thing or a bad thing.
At any rate, their interaction was a great source of humor. Using movie references during their fight with the Wrecking Crew gave me a good laugh. Deadpool asking Spider-Man to confirm that he wasn't hallucinating when the Punisher intervened dressed as three different super-villains also cracked me up. The "Steve Ditko" comment was great. And finally having Deadpool encourage Punisher to urinate on The Wrecker was something completely unexpected and yet completely appropriate for Deadpool to say. Sophomoric mercenaries can be very entertaining.
It wasn't explicitly stated in this series why Tombstone would agree to go double-or-nothing with Conrad on this bet. Or for that matter, why Deadpool was chosen as the target. My best guess is that Conrad was somehow able to goad Tombstone into taking the bet. He figured he had nothing to lose and it should be easy for someone like him. As we saw in the helicopter sequence, Tombstone has the Marty "Nobody calls me chicken" McFly temperament and can be easily manipulated.
4 webs. The motivation behind the bet and choosing Deadpool as the target was never clearly established. This in turn reduces the score. Deadpool *was* inadvertently responsible for Conrad losing the bet,but that seems to be too loose of an association. To dedicate this much time and resources to win a bet, there should be a believable reason Tombstone chose Deadpool.
In any event, despite a few items, the series was fun to read. The pacing was nearly perfect, the dialogue was great, and Barberi's artwork was incredible.
Punisher broke into a cache of super-villain weapons in Punisher (Vol. 7) #2. This explains the goblin glider, pumpkin bombs, etc.