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Timeline
Zero
• Born to a seemingly-healthy mother and father.
• Mother is a house wife.
• Father is Army Veteran // Police Officer

Five
• Begins to have deranged fantasies, often involving killing mass amount of people.

Eight
• Parents become aware of his psychopathic tendencies.
• Deranged fantasies become more severe and occur more often.

Nine
• Parents hire a psychologist to work with him.
• Mother is diagnosed with cancer.
• Father becomes an alcoholic and takes a part-time job as a hired clown for entertainment to pay for the personal psychologist.

Ten
• Mother dies of cancer.
• Father consistently beats Wade, wearing his clown costume at times.
• Wade overhears his psychologist talking to his father about a mental institution.
• Kills the psychologist; as a police officer, father sweeps it all under the rug.
• Father quits part-time job.

Eleven
• Oddly develops a "friendship" with his father.
• Trains with father in hand-to-hand combat and whatnot.

Fifteen
• Enrolls in school for the first time.
• Is expelled his second day after kicking the s**t out of three other kids and a male teacher.
• Becomes very skilled at fighting.

Sixteen
• Father tells him about his mother's life insurance money.
• Father dies due to being accidentally shot by a drunk friend.
• Wade is formally introduced to firearms.
• Saves insurance money.
• Steals food and money to survive.

Seventeen
• Becomes proficient with firearms.
• Meets his first real friend, a Japanese foreign-exchange student.
• Starts learning swordsmanship.

Eighteen
• Becomes proficient in swordsmanship.
• Kills friend while sparring.
• Runs and hides from the law.

Nineteen
• Gets involved in mercenary work, most notably traveling to Asia.
• Disobeyed orders and did the exact opposite of what his assignment was.
• Travels to the U.S.

Twenty
• Joins the U.S. Army.
• Receives additional military training.

Twenty One
• Joins the U.S. Army Special Forces

Twenty Two
• Dishonorably Discharged due to constant disobeying of orders.
• Recruited into Weapon X.
• Discovers he has cancer.
• Receives his Mutant Healing Factor.

Twenty Three
• Again, disobeyed orders while under Weapon X.
• Sent to the Hospice, a place for failed operatives.
• Tortured and experimented on.
• Survived an execution (Ajax ripped his heart out of his body).
• Escapes from Hospice after killing Ajax.
• Names himself "Deadpool."

Twenty Four
• Uses money from his mother's life insurance to buy equipment, an apartment in Arizona, and, perhaps most notably, has a large amount of custom "costumes" created.
• Goes back into mercenary work.