John Constantine has been many things to many people over his long and storied career in comic books: a charming con man, a reckless sage, a star-crossed drinking buddy. Yet one constant for the character – aside from his penchant for silk-cut cigarettes – has been his ability to negotiate his morality for the sake of a plan.

RELATED: 5 Times John Constantine Was A Hero ( &5 Times He Was Worse Than The Villain)

Of course, it's usually Constantine himself who benefits from these various plans, damn the fates of the others involved. But what are the choices he makes that would cause readers to cringe? What are the most morally questionable things that John Constantine did?

10 Being Cold To A Dying Man

As one of the only Americans to write Hellblazer, Brian Azzarello took Constantine out of England and smack-dab into the United States. His adventures yielded many squeamish results, but one of the worst things Constantine did was literally talk a man to death.

In Freezes Over, Constantine is held hostage by gunmen during a snowstorm. One of the gunmen, Lamar, has a gunshot wound and is bleeding profusely. While Lamar is watching the captives, Constantine begins speaking to him, keeping his focus off of the injury, letting him bleed to death. Now that's ice cold.

9 Giving Demon Blood To His Poor Protégé

Angie Spatchcock was an aspiring witch working in a diner when her paths crossed with John Constantine. Ever the sucker for a pretty face, he brought her into his world, using her nascent magical talents to work on a scouting mission for him. Her night ended in a hospital, covered in her own blood.

Yet that’s not the worst part in this tale from Red Sepulchre: Angie was comatose, barely hanging on to life, but in order to revive Angie to get information Constantine injected his tainted demon blood into her IV bag.

8 Right In Front of Grandad

For years Chas has been one of Constantine’s best (and only) friends. Readers got to see him age in real-time alongside Constantine. In All His Engines, readers also saw Chas’s granddaughter Trisha captured by a demon named Beroul and held hostage unless Constantine became Beroul’s errand boy.

RELATED: Justice League Dark: 20 Of The Most Powerful Members, Officially Ranked

Ever the strategist, Constantine enlisted an ancient Aztec god to destroy Beroul and restore Trisha. However, the god took possession of the girl, and Constantine threatened to kill Trisha to destroy the demon. The god released her, but Chas never forgave his friend.

7 Mocking An Angel In Rock Bottom

Gabriel the archangel is most assuredly a snob. He dwells in the poshest English gentlemen’s club, harshly judging anyone who manages to get into his presence. Once, in need of a miracle, John Constantine came to him and was dismissed.

Constantine took that grudge and pushed it until it became a mountain of hate. In Fear and Loathing, Constantine enlisted his succubus friend Chantinelle to seduce the angel and literally rip the heart from his chest. As if that wasn’t bad enough, Constantine gloated as he shredded Gabriel’s wings off with a chainsaw.

6 Intentionally Losing His Innocence

Constantine’s pursuit of magic over his lifespan has been a twisted thing, especially in regards to what (or who) he would be willing to sacrifice to gain the upper hand. Apparently, he’d even sacrifice a bit of himself, like in the Books of Magic/Hellblazer crossover.

As a child Constantine removed his own childhood innocence, considering it a weakness. Stripping himself of that special part of youth sent him down his path to the supernatural. Years later, young magician Tim Hunter found it and offered it back to Constantine… who declined it.

5 Fibbin’ His Family

In The Devil’s Trenchcoat, Constantine visits hell to find his sister Cheryl. What’s more shocking was when he learned she chose to be there, damning herself for giving up her first child. John promises to find her son, as long as she will let herself leave hell. She agrees and ascends. Except…Constantine lied.

The First of the Fallen tells Cheryl the truth – that Constantine never actually intended to search for her son – and once his lie was exposed, she went right back to hell, righteously ticked off at her brother.

4 Still Being a Jerk After Rebirth

After being cursed by a demon, Constantine fled London to keep the mystical sickness at bay. But in the Hellblazer: Rebirth special he shows how stubborn he is and returns to his hometown and transfers the curse onto the entire city.

The demon, staring down the barrel of having to collect eight million additional souls, announces he won’t remove the curse unless Constantine had its true name. With the help of a psychic friend, Constantine bluffs the demon into removing the curse with its name, leaving moments to spare. Was he remorseful? Nope.

3 Trapping The Lord of the Flies

Constantine Hellblazer Shoot

In one of John Constantine’s first solo adventures, an escaped African hunger demon is killing London citizens. Brought to the UK by his old Newcastle pal Gary Lester, the demon burns out its victims, leaving only emaciated husks.

After consulting with Papa Midnite, Constantine learns the only way to capture the spirit is to trap it in a living vessel. He uses the demon’s desire for revenge against Lester, trapping it inside his former friend. He leaves Lester in an insane asylum, with the demon eating him away from the inside.

2 Good-Bye, Ritchie

Another friend, another letdown, this time terminal: Another of John Constantine's Newcastle friends, Ritchie, finds a way to combine magic with machinery, becoming a bit of a technomancer. Constantine enlists his services to get information on a rogue occult group by going into the internet.

RELATED: Constantine: 10 Facts To Know About DC’s Hellblazer

Unfortunately, something goes terribly wrong while Ritchie is inside the web, and his body spontaneously combusts. Constantine is mortified, and instead of explaining to Ritchie's consciousness what happened to its body, Constantine unplugs the computer, banishing Ritchie from the physical plane.

1 Betraying His Best Mate

In a recent Hellblazer story, readers saw John Constantine at the end of the world: Future Tim Hunter has unleashed hell, and Constantine needs to distract the Great Enemy for good magic to attack. Enter his closest friend, Chas.

Constantine tells Chas to take a “magical nuke” into the heart of madness to destroy it. Believing his best mate, he drives off into the mayhem, and it’s not until the end he realizes that he’s been lied to. The distraction doesn’t even work, and Constantine condemned his most loyal friend.

NEXT: Poison Ivy Vs Swamp Thing: Who Is The Better Guardian Of The Green?