Bob is, in every respect, a normal guy. He signed up for Hydra believing that they have a dental plan (which they don't), and made $40,000 a year. Bob kept a blog while he was at Hydra, primarily remarking about the mundane like complaining about the commissary food. When Agent-X was captured when a pharmaceutical company hired him to infiltrate Hydra, the mercenary known as Deadpool mounted a rescue operation to free him.
At the time Deadpool was only three inches tall due to exposure to Pym Particles. His height did not stop him from taking down several Hydra agents before finding Bob. While Deadpool was beating an unnamed agent, Bob came running down the corridor to locate the intruder and was tripped by the tiny merc. Wade commanded Bob to take him to where Agent X was being held. Believing that Deadpool could not hurt him, Bob refused. Deadpool then hurt him... twice (because it was so much fun the first time). Deadpool used the string from a retractable I.D. card reel to aim Bob's head, and (somewhat) forced Bob to shoot his fellow Hydra agents. After being abused and mistreated by Deadpool, Bob introduced himself. Deadpool recognized Bob from his blog.
On the way out of the facility with Agent X Deadpool shot Bob so that he could claim he was being held at gunpoint and rejoin Hydra. The three stole a Hydra plane and Deadpool forced Bob to pilot it away from Hydra. Wade now runs Agency X in Agent X's stead and has kept Bob on as a teammate. His opinion of Bob changes from moment to moment, but generally regards Bob as either a friend or a pet. Bob is not unhappy with Deadpool, but may believe himself to be kidnapped from Hydra (Deadpool refers to the kidnapping as a "liberation"). Wade's friend Weasel was also taken into Hydra custody, and when Wolverine attacked the Hydra base that Weasel was at Wade was afraid that Wolverine would kill Weasel during the carnage. Deadpool forced Bob to tag along as an insurance policy. Unbeknownst to Bob, Deadpool planned to (possibly) trade Bob for Weasel if the need arose (but he would not admit this to Bob).
Mayor Story Arcs
Bob stayed with Deadpool after their initial encounter, because he had nowhere else to go. He and Deadpool had a few adventures, also traveling to several different mystic realms on behalf of Doctor Strange, to save the whole multi-dimensional existence by freeing T-Ray, and fusing his soul and body back together. They go to a swamp and meet Brother Voodoo, and Bob is knocked out and given nightmares, and Deadpool does all the work.
When they finish up, they return back to the Agent-X base. There him, and the rest of Agency X watch as Deadpool and Agent-X negotiate Deadpool's contract, by shooting at each other. Bob, Deadpool, and Weasel are then sent to the Savage Land. They get back to New York, and it has been infested with symbiote dinosaurs. Bob hides. Then one of the dinosaurs tendrils grabs Bob by the foot and starts to drag him away. While Bob is being dragged around the dinosaur, the dinosaur hits an electrical billboard, it falls on the dinosaur killing it. A reporter comes up to Bob asking him if the H on his uniform stood for hero because that's what he truly is?! Bob replies by saying: "Yes, it does stand for hero because that is what i truly am!". He then gets a text from his wife saying she saw him on T.V. and that he looked hot. Then Bob and Agency X is seen at Deadpool's place watching T.V.
Bob is seen in Dark Reign helping Deadpool by shooting a bullet at Tiger Shark, who is attacking Deadpool. Tiger Shark then takes Bob underwater. Deadpool then pulls Bob and the rifle he had out of the water and asks Bob how he found him Bob replies: "Saw you on the T.V." The next morning Bob and Deadpool are eating some food, Bob then grabs the rifle and says he's sorry but if he doesn't kill Deadpool the guy who hired him will kill him. Deadpool tells Bob that the person he should be afraid of is him. Tiger Shark comes in and Bob is sitting on the bed holding the rifle, Deadpool then attacks Tiger Shark and shoots him out the window. Deadpool then proceeds to shoot Bob in the hand for pretending to betray him. Bob then tells Deadpool that the man who hired him was Norman Osborn. Deadpool sends a note to Osborn saying he killed Bob and is coming for him. However, Bob turns up later to join Deadpool as a pirate. One day bob gets a cassette player with headphones and a tape in it from deadpool telling him to come join him because they are going to be pirates. Deadpool then dresses up as a pirate and makes bob dress up as his parrot and squawk before he says anything, deadpool shows bob some "tough love" but he catches on.
Six weeks later they hit land and are looking for a vet(because he is dressed as a parrot). They come across this need to find something ask booth, and inside is a blind girl that knows the island. While they are talking to the girl real pirates start attaching the island. Bob then tells the girl that Mr. Wilson has a lot of guns, then she asks who that is. Bob then proceeds to tell her that Mr. Wilson is the most feared and most badass-est mercenary in the entire world, and because he just got rich that he will defend the island for free. Deadpool agreed and Bob payed by being beaten with the stick for 5 minutes. So Bob rowed deadpool and the girl to Deadpool's ship to find out it was stolen by the other pirates. So Bob distracted the pirates while Deadpool took his ship back. After Deadpool went unconsious due to loss of blood, Bob used a machine gun to try to take out the other pirates ship but missed badly. After Deadpool regain consiousness he took out the other pirates ship by blowing up a nuclear sub making a tsunami that put Deadpool's boat onto shore. The girl asked if Bob could stay and protect the island but Bob declined saying he's married. Deadpool went to sea and left Bob on the island with a treasure chest of gold.
Hulked Out Heroes
In this arc, Bob has begun working for A.I.M. after being recruted by a (literal) headhunter. He wears the standard uniform but he still has his Hydra mask on underneath. Of course, since Bob is here, that means that Deadpool is not far behind, though he has since become Hulkpool. And Hulkpool hates Deadpool, so he recruits Bob to help him go back in time, using Dr. Doom's time machine, which was stolen by Red Hulk and Thundra, and kill Deadpool. However, Bob has trouble with the machine and creates some problems. Long story short, the first American President was The Thing, Captain America and Bucky were not caught in a missile explosion and instead bombed Hitler and Red Skull, every major superhero was prevented from experiencing the event which led to their life of heroism, and Bob became the new name for God. But these events became part of an alternate time line, so it had no effect on the real universe. So nothing was accomplished, save for Bob being stranded in the middle of the desert
Bob managed to get back home, where he took up his dream of growing genetically altered popcorn. Just as he had successfully grown the world's largest popcorn kernel, Deadpool crashed through his house and destroyed it. Bob texted Macho Gomez, who had organized a group of Deadpool's former friends ( Blind Al, Big Bertha, Weasel, Sluggo, and Taskmaster) furious at how Deadpool had treated them. Bob refused to be part of the fight, but ended up being shot in the leg by Deadpool anyway.
"He's like Deadpool's biggest and only fan. He thinks Wade is a guy who's got it together, which speaks volumes about how monumentally dysfunctional Bob is. He's kind of a supplicating sycophant, but I want to explore more of who Bob is and see if there's more to him than just that." - Daniel Way (writer)
Bob is a normal guy in absolutely every way. He is thirty-three, and possesses average (or below average) strength, agility, durability, and intelligence. Bob continues to wear his Hydra uniform despite his "liberation".
Bob "excels" in Stealth, thanks to the classes taught at HYDRA. The classes taught at HYDRA were Tactics of Retreat 101, Advanced Tactics of Surrender, and Hiding Places 301. Due to these classes, Bob is able to avoid danger most of the time.
In Deadpool Max, Bob is Deadpool's CIA handler. He was raped for weeks as a plan to kill the head of the Maggia crime family. In this universe, nobody believes Hydra exists except Deadpool. Bob uses this belief to control Deadpool by claiming targets are Hydra heads. He also claims he used to work for them. Despite nobody believing Hydra exists, Bob dresses in the Hydra attire and is shown wearing a ring with the Hydra symbol. Bob had a past relationship with a fellow handler, but she went rogue, messed up his life and caused him to be put on death row, and was claimed dead, later proving otherwise.