|“||I was cocky. Never actually thought I'd lose. But I was wrong. Dean...I was wrong.||”|
Dean and his brother Sam had a falling out. Shortly after, Sam chose to say "Yes" to Lucifer in Detroit. By obtaining his true vessel, Lucifer was able to decimate the human population and unleash the Croatoan Virus.
Realizing this, Dean offered to become a vessel for Michael, and despite going blue in the face from screaming for Heaven's attention, but the Heavenly Host had abandoned Earth, leaving Lucifer the undisputed winner of the war.
At some point, Dean gathered surviving humans and formed a team of resistance fighters that battled demons and annihilated anyone infected with the virus. The angel Castiel stayed by Dean's side as he slowly became human.
In 2014, Dean found another version of himself from the past, sent here by Zachariah. Knocking him out, he brought him to his camp and saw that he was a human after doing tests. Once his counterpart woke up, he informed him of how got sent there from 2009. Though suspecting of Zachariah's strategy, he has him further confirm his identity. Past Dean revealed a personal secret only they knew, which was their preference in wearing pink satin panties. Future Dean knew the person really is him but doesn't let him go.
Due to their different experiences, the two Deans did not see eye-to-eye. After obtaining The Colt, 2014 Dean decides to go on a suicide mission and confront Lucifer once and for all. Although his men know that they was a high chance of dying on the mission, they all agreed to participate. Past Dean also joined them on the mission, even though he thought it was highly reckless. Before leaving, he instructed his counterpart to consent to Michael and reveals Sam's fate as further reason to do so but realized the latter won't do it.
In Detroit, Dean ordered his men to act as decoys while he confronted Lucifer alone. To prevent his counterpart from intervening, he knocked him out and went to confront his enemy himself.
Unfortunately, the archangel easily overpowered him and by the time Past Dean arrived, Lucifer was seconds away from snapping Dean's neck with his foot and he shared one last look with his counterpart before he was killed. His death took away all hope of humanity reclaiming the planet.
This Dean was described as ruthless. He had become cynical after five years of fighting a losing battle against the forces of Hell. He was willing to kill anyone who showed signs of being infected, and did not allow his men to give suggestions. He was keen on using torture for interrogation. He was willing to sacrifice his men in order to defeat Lucifer.
Dean's biggest regret was not saying "Yes" to Michael when he had the chance. He even ordered his counterpart to say "Yes", as it would promise mankind a fighting chance against Lucifer. His pleas ultimately fell on deaf ears, and he too died due to his reckless and "do or don't" nature.
- It is unknown if Dean ever managed to use the Colt on Lucifer before being killed. However, either way it wouldn't have worked because, as revealed in Abandon All Hope..., Lucifer is one of five things that the Colt cannot kill.
- This Dean was killed in 2014, the same year his counterpart was briefly killed by Metatron.
- This Dean's goal of killing Lucifer was ultimately accomplished in 2018 of the Main Universe when Dean killed Lucifer with the help of Apocalypse World Michael.
- When his world ended, Dean attempted to say "Yes" to Michael but was ignored. He later urged his present-day counterpart to do what he was unable to do, but he initially refused. The present-day Dean later said "Yes" to the Apocalypse World Michael with conditions in a successful effort to defeat his Lucifer.