If you know Deadpool, there is a big chance you have at least heard about Taskmaster, One of their most iconic interaction being the battle they have while Deadpool was shackled. Taskmaster’s line “The things I do for friends I can’t stand” comes from there. (For those who want to check that battle out it’s Cable and Deadpool #36).
Meeting and the consequences
The first interaction we see of the two is in
Deadpool Vol 1 #2 (February 1997), Wade and Taskmaster knew of the other but had never met before and they didn’t get to meet on good terms. Taskmaster ‘kidnapped’ Weasel to offer him a new job, Wade tracks Weasel to one of Tony’s many training schools and starts fighting, Tony observes him through the camera-feeds and copies Wade’s moves. Tony states that Wade’s moves are redundant (repetitieve and unneeded) as he uses them on Wade.
When Wade comes to he is informed about the job offer by Weasel and that he is considering to accept it, Wade won’t have any of that of course. So Taskmaster decides to battle Wade in front of his pupils to try and convince Weasel he’s the superior mercenary and thus a better employer (more money coming in).
Now Taskmaster can copy everything he sees, later on a misunderstanding was formed that he couldn’t copy Wade, this isn’t true, but the mistake stems from this comic, their first appearance together, since Taskmaster can indeed copy Wade, he can not predict Wade, not like he can predict other people he studied. Mostly because Wade can’t really predict himself, so how would anyone else? So at first it looks like Wade is going to lose until he gets serious (since his friend is on the line).
Taskmaster swears to learn to understand Wade and tame his chaotic nature as a form of revenge after he is beaten, to which Deadpool leaves after giving Weasel a wedgie (because he’s a delightful friend that way).
In Deadpool Vol 1 #35 (December 1999) we learn in a flashback that shortly after their first meeting they were both hired as henchmen by the Wizard, something that didn’t really end well for any of them. of course a lot happens off panels that we get hints at but never gets fully explored.
In Deadpool Vol 1 #39-40 we see Deadpool take a gig for Taskmaster instead of Titania (actually Copy Cat) where he goes up to a space station with three of Taskmasters trainees, it’s actually a trap to take revenge on Wade for humiliating him. Sending a fat mind wiped Wade into Space.
Of course in Deadpool fashion he survived had an epic space adventure and returns back to earth so that in Deadpool Vol 1 #45 it can be revealed that it is in facts Copy Cat and not Titania he and Constrictor had been living with. It is revealed that Copy Cat was working for Taskmaster and Wizard to get revenge on Wade for his failures while working with them and for humiliating them.
Copy cat gets Wade’s bank codes so she can rob him blind, after which Wizard blows the home Deadpool had been staying at up, Taskmaster seemed to be content with the amount of damage they had done to Wade as payback, seeing as they realized they couldn’t actually kill him.
Respect for the dead
It’s in Deadpool Vol 1 #67 (July 2002) - Deadpool Vol 1 #69 (September 2002) that we see Taskmaster make his appearance again, as Deadpool made a name for himself as mercenary having a big office and a manager/assistant Sandi; who turns out to be a friend of Taskmaster. (after taking credit for a hit taken by Black Swan, but Wade didn’t know he didn’t hit them).Wade’s mind has been infected with a virus by the black swan as payback for stealing the credit, Sandi asks Taskmaster for intel on the situation.
Taskmaster has grown to respect Wade by now, they have a drink together where they exchange the intel and even though he still thinks Wade is mad, it also seems to be what he enjoys about Wade. He even offers to go on the hit with him, when Wade thanks him for it he quickly states it’s so Sandi doesn’t lose her job (but he later expresses a fondness for Wade in Agent X #1).
Since Deadpool goes after black swan on his own and died (for a second time in his run) and Alex Hayden shows up Taskmaster is convinced Alex is actually Wade pulling the amnesia stunt, which he expresses a hate for (I got some bad news for you Tony). Tony accepts in the first comic of the agent X series that Alex is indeed not Wade, but still somehow is convinced Alex might still be Wade somehow (since Alex has part of Wade’s brain he’s not exactly wrong).
Alex his instinctual hate for Wade makes Alex shoot him (the guy is in the body of a Dead guy who believes Wade killed his brother, has some of Black Swan’s hate for Wade and has Wade’s self loathing, no wonder his first instinct is to shoot Wade through the head). Taskmaster and Sandi instantly try and patch Wade’s skull back together so it can heal better (Stapel gun Tasky really?)
All of the members of Agency X work together to undo what has been done due to Black Swan and work together for a while outside of comic view, next thing we hear of Deadpool is alongside Cable.
(Also bonus panel from agent X 3: Inez (left) and Sandi (right) discussing if Alex and Tony should kiss, important to note that both of these woman are friends of Tony)
Friends I can’t stand
As said in the introduction
Cable & Deadpool Vol 1 #36 (January 17 2007) holds one of the most iconic interaction between these two doofs mainly one of Wade’s crazy ideas to proof to the world that he is indeed a great mercenary.
He breaks out Taskmaster telling him he just wants to fight him, Taskmaster agrees realizing Wade needs a reputation boost, to which Wade knocks him out cold because it’s easier for him.
Wade gave himself a challenge by manacling himself to fight Taskmaster making it more challenging for himself that way. He still managed to win simply due to his healing factor.
Expressing his respect for Deadpool’s skill Taskmaster leaves reminding Wade once again he has to learn to be professional (aka tame that chaos in his head).
In Thunderbolts Vol 1 #130 (2009) Deadpool is messing around with Osborn and his Thunderbolts, we see Deadpool hire an unnamed party who then stays incognito.
In Deadpool Vol 2 #9 (June 2009) they meet up in a warehouse building where Taskmaster isn’t so supportive of Deadpool’s crush on Black Widow, they have some really humorous insult banter together until Wade tells him to disguise as him if he wants to get paid.
Where as in Thunderbolts Vol 1 #131 we see Taskmaster who is pretending flawlessly to be Deadpool getting captured and of course saved by Wade before getting paid from several ATM’s using Osborns gold card.
Kill me if you care
In Deadpool Vol 2 #36 (April 27 2011) Wade sets out to find out if his friends love him. Meanwhile most of his friends have banded together to kill him. Wade sees this as a betrayal until Death reminds him this is exactly what he wanted from his friends, what he has always pushed them towards. That them wanting to kill him meant that they cared.
Battle Scars Vol 1 #3 (January 11 2012) Taskmaster was hired to go after Sergeant Johnson and Wade was lied to and told the guy killed his mom so Wade was going after him as well. Taskmaster stabs Wade to make him pause from killing Johnson to avoid losing his contract.
Deadpool ends up saving both Taskmaster and Sergeant Johnson before it turns into an all out brawl with other mercenaries since everyone seems to be after Sergeant Johnson.
When Wade no longer has his healing factor he realized he had to relearn what he had forgotten due to his years of being careless. Wanting to relearn how to be a mercenary who could survive without his healing factor he trusts on Taskmaster to be able to do so.
In Deadpool Vol 2 #56-57 (July 2012) Wade asks Taskmaster to teach him for free, Taskmaster decides to take him along on a mission with him, telling Wade he wanted to do this two mans job with him and him alone.
Taskmaster took wade along as a distraction, while he was inside waiting for Wade to join him Wade convinced himself Taskmaster had send him to die. Still he went to save Taskmaster from S.H.I.E.L.D. guard robots, but he was very mad about the whole deal, which Taskmaster made worse by revealing he had sold Wade out to Black box.
Taskmaster got away from Wade alive, only to have Wade ‘come after him’ in Deadpool Vol 2 #62 (October 2012). After a small fight Wade reveals he’s there for a job and willing to forgive Taskmaster (gassing him with a taco bell fueled gas attack first). Taskmaster reveals that some of Wade’s enemies are in town before he wants to discuss jobs, but Wade suddenly is more interested in the enemies than the job. Taskmaster gives him the info before contacting the team of enemies about Wade being on his way in return for money (Tasky sure loves his money doesn’t he?)
In Deadpool Vol 3 #10 (May 22 2013) we see Taskmaster make a brief appearance as a merc hired by someone who Wade wants to take out, but Taskmaster asks Wade to take him out because he really doesn’t care about the job.
On Deadpool’s wedding (Deadpool Vol 3 #27 April 2014) Taskmaster is one of the guests who before leaving talks to Wade a bit about love and the life they both had chosen.
Mercs for Money
Everyone who ever read Marvel knows that continuity ain’t exactly their forte. This shows once again in the Mercs for money mini series. In this 5 issues miniseries Tony appears in issue #2-#4.
We meet up with Tony in issue #2 where he gets approached to steal from Deadpool, something Tony said would make his day even better than it already was.
At the end of the issue we seen Evil Deadpool approach Tony saying they are hired for the same gig and that he considered working together, but it was neither of their style’s so he tells Tony they should just kill eachother.
The great thing to happen in #3 however is the fact that the normal Deadpool is the one who narrates the fight and he he makes a remark about there being sexual tension between Tony and his evil self.
Tony managed to take down Evil Deadpool, but he gets away with a trick (letting his detached hand shoot Tony from behind. Tony misses his shot to fulfill his mission then and there and tails the Mercs.
Jump to #4 the last that has Tony, Tony has a chance to take the cargo and leave without a fight but instead choses to attack the Mercs.
He states that it is to pretend them from following him, but Tony is a pro at shaking off tails so I kind of doubt that would be the canon reason, especially because a statement later on makes it seem more personal than that.
Wade knocks Tony out from behind while he’s focused on his opponent and that’s the last we see from Tony around Wade. Just one extremely bitter Tony talking about how selfish Wade is.
So what happened between the wedding and now? We know there is a time gap of a few months in Marvel’s canon as they never really show how Wade suddenly became popular, did something happen then between him and Tony? Or did Jordan D White’s team just decide that it be more interesting for Tony to suddenly hate Wade again. It doesn’t seem like Tony to risk his connection with the one person who knows what he looks like.
While they started out as enemies Wade is one of the few people who Taskmaster showed his face to (Bonus: might even have left a mask at Wade’s place), They have a love/hate relationship but they both confirm their friendship at several occasions and Wade is the only person Taskmaster has revealed to be able to remember since the amnesia retcon from 2010.