To most, the Punisher is a ruthless, cold-hearted killing machine, whose only focus is revenge. The fiery flames of love cannot melt his frozen, stone cold heart, nor make a dead heart beat with a purpose other than vengeance. After the brutal slaying of his beloved wife Maria and two children by the mob, can he ever be expected to love again? The answer is...complicated to say the least. Some would argue that love, or even sex for that matter, aren’t even on Frank Castle’s radar.
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A relationship, hell even just casual hooking up, would make him soft, and shift his sights from where they should be -- eliminating the cesspool of criminal activity in NYC and raining retribution in bullets on those that made his family suffer. Others might say that a man has needs, and even an effective killing machine needs his fires stoked every now and again. Regardless of where you stand on the matter of romance having any business being in a Punisher storyline, the Punisher has gotten lucky many times. CBR explores his Queens of the Castle, the ladies who contributed to the 15 times the Punisher got lucky, and what each one meant to his reign of revenge.
15 KATHRYN O'BRIEN
If there was any woman who stuck around long enough to go from random hookup to regular fling, it was Kathryn O’Brien, who was a badass in her own right. In The Punisher Vol. 6 #1 story, "In The Beginning", we learn her corrupt boss at the CIA wanted her to apprehend the Punisher to protect his heroin operation in Afghanistan, but the mob interrupted their stake out. She’s eventually left for dead in Afghanistan by her CIA partner/ex-husband Bill Rawlins.
Hellbent on taking revenge against all the deadbeat dudes that did her wrong, she teams up with the Punisher from time to time to kickass and hook up. The Punisher sees a kindred spirit in Kathryn, and she with him. They don’t beat around the bush about why they’re sleeping together, and there’s a certain amount of comfort in shacking up with someone who has no expectations.
14 BLACK WIDOW
In the anime film Avengers: Confidential, the Punisher is taken into custody by S.H.I.E.L.D for interfering in what was supposed to be a top secret mission. In order to be set free, the Punisher has to team up with Black Widow on an assignment to prevent stolen S.H.I.E.L.D technology from being sold on the black market by a terrorist organization known as Leviathan.
Because Punisher does what he does better than anyone in the world, defying authority and killing some people that Nick Fury wanted to question, the terms of his release are void. The responsibility of what to do with him is left up to Black Widow, who promptly kisses him and lets him “accidentally escape”, the ultimate sign of love between two highly-skilled killers.
13 LYNN MICHAELS
NYPD Officer, S.H.I.E.L.D operative, and even Lady Punisher. It’s hard to believe that while jogging through central park, she could be attacked by a mugger and not break his spine in five places and make him eat it. The Punisher intervened, however, and though the thug got away at first, they hunted him together and bonded in the process.
The Punisher would call on Lynn again at different times and, when she’d become particularly disgusted with the legal system, she would come to don the mantle of Lady Punisher to take justice into her own hands. When the Punisher saved her life from the assassin Stiletto in The Punisher Warzone #7, "Mugger’s Picnic", she kissed him for the first time, indicating deeper feelings than their partnership had revealed.
12 PAINKILLER JANE
The Punisher has a weakness for violence-loving vixens that can hang with his lifestyle. Enter Painkiller Jane, an ex undercover cop who got blown out a 12-story window by a planted explosive device while trying to go after the Fonti mob. She has the ability to regenerate, and is pretty much indestructible, a combo that means she an survive almost anything.
When Frank Castle comes face to face with Painkiller Jane in The Punisher/Painkiller Jane #1, there’s an instant attraction on Jane’s side, who has never been affected by a man that way before. The feelings aren’t exactly mutual, but Jane is very persuasive, and soon the pair form a relationship with shades of the Joker and Harley Quinn from Batman: The Animated Series, with Frank begrudgingly tolerating Jane’s lovesick declarations.
11 A RANDOM PROSTITUTE
In Punisher: Return to Big Nothing, we encounter a miserable Frank Castle who has to deal with constant flashbacks of his massacred family and the hard truth of an old ‘Nam buddy being responsible for killing US soldiers and using their corpses to bring contraband across state lines. In between waiting for shady drug dealers to meet up and make their shady exchanges, Frank visits a brothel where he picks from a selection of ladies.
He reminisces how the perfume they wear reminds him of his dead wife. This Punisher has to get it on with the lights out, and not because he’s shy, as one companion suggests. Rather, if the lights are out, and he’s simply feeling the form of a woman, he can imagine it’s Maria, and for a moment let the rage subside a little.
10 WILD ROSE
In The Punisher Vol. 2 #7 story "Wild Rose", The Punisher stops a group of terrorists from getting their hands on some plutonium, sparking the curiosity of Rose Kugel, an Israeli operative that has also been keeping tabs on certain terrorist Jihad activities. She follows him to his warehouse to find out more about him, and realizes they have many common goals.
When they team up to infiltrate the First World International Terrorist Convention in Empty Quarter, she poses as a courtesan and he poses as a known terrorist called Saracen. He is offered her beguiling company by the sinister organizer of the convention, Jackal, and to maintain their charade, they go to bed together before getting to work planting a bomb on site. It was the Punisher that gave her the nickname “Wild Rose”, presumably after their desert dalliance.
9 VICKI WHITE
One might say that Frank Castle had to have drunk some sort of kool-aid to have gotten with Vicki White. In The Punisher Vol. 2 #5, when the Punisher goes after Reverend Sammy Smith at his compound of Smithtown in Guyana, he encounters her while trying to ingratiate himself to the local population of worshippers.
They have come to live with Rev Smith to cast off the trappings of conventional society, with its greed, hubris, and material obsession, in favor of living a simple, unfettered life in a shared commonwealth. She seems to think that sleeping with Frank will make the Reverend happy, and so offers herself to him. Frank doesn’t want to blow his cover and obliges her, though this is most likely in an effort to get closer to the Rev and make him a true believer in pain.
8 JOAN
In The Punisher Vol. 4 #1, "Welcome Back Frank", Joan is a skittish neighbor who is scared about everything in NYC and just wants that country life on a farm with a dog. In The Punisher movie from 2004, Joan is a fox played by Rebecca Romijn, who isn’t so much terrified of NYC as Frank Castle when he takes refuge in the abandoned apartment she’s inhabiting.
In both versions, Joan helps tend to Frank’s wounds one night, and they develop a rapport. In the movie, it’s clear that Joan has the hots for Frank, but in true Punisher fashion, he doesn’t let their relationship develop enough to warrant her getting in danger. This doesn’t mean they don’t engage in some heavy PDA and lots of bedroom-eye glances but ultimately, like so many ladies on this list, the Punisher leaves her a stack of bills and never calls her again.
7 FLO
During the period of time chronicled in The Punisher MAX series of issues #1-#22, the Punisher goes after a series of mob bosses, including the “Kingpin of Crime”, though in this version the title is almost mythological, and is given to a bodyguard named “Wilson Fisk”, who embodies the figurehead of the crime syndicate.
Bullseye, the world’s greatest assassin, soon becomes in league with him, and takes on the Punisher in a deadly confrontation that sends Frank Castle to a maximum security prison. It’s there, surrounded by enemies, that he contemplates the Punisher persona, its meaning to him, and what it represents in his life. When he gets out, he does what any man who’s spent any time in the pen will do; finds a prostitute named “Flo” and gets some pent up angst out of his system.
6 JENNY CESARE
Have you ever wondered what it would be like if one of the Real Housewives of NYC decided to massacre the remaining members with a baseball bat? In The Punisher #43-#49, Jenny Cesare, a member of a prominent mafia family, has her marriage arranged by her sister and various Mafia wives. Her husband is complete wife-beating scum. When she threatens to go to the feds and expose his criminal activities, her sister and her husband’s thugs beat her and toss her in front of a train.
Due to goon incompetence, she doesn’t die, and is now free to unleash pain on all the women that knowingly set her up with an abusive jerkhole. The Punisher has already taken out her husband, leaving her to take care of the rest. Afterwards they bang, but Jenny just doesn’t get much out of sex anymore and promptly shoots herself in front of Frank.
5 REIKO
Because assuming aliases to bang women worked so well before, the Punisher adopts the sobriquet “James Maxwell” in The Punisher: Assassin’s Guild to investigate the Assassin’s Guild operating out of the Thousand Autumns Chinese Restaurant. He’s tailed Reiko, an assassin contracted by a man to avenge the murder of his daughter, Gracie Williams, during a traffic accident.
Reiko isn’t stupid and immediately pegs Maxwell as the Punisher, but when he asks her to dinner, she doesn’t refuse. She also doesn’t refuse the romantic interlude that comes later. Though their target is the same, they agree to not step on each other’s toes, and the Punisher and the Assassin’s Guild reach a truce, coming to each other’s aid as needed. In fact, any contract out on the Punisher that reaches the Guild gets refused from thereafter.
4 ALICE HOFFMAN
Crips and the Bloods selling crack! Skiing armed combat! A Kamchatkan warlord trying to destroy the Alaskan pipeline! Sounds like the Punisher is just the eco-friendly humanitarian to put a stop to it! In The Punisher War Journal #31-#33, these plot points all actually happen and Frank Castle is sporting an alias (again). He’s joined by movie star Alice Hoffman who up until now has made millions of dollars but not a difference in millions of people’s lives, so she became part of a radical humanitarian group called Humans Off Planet.
Though she once allied herself with the Kamchatkan warlord because he said all the right things (think “international socialism”), she now sees he’s corrupt and just wants to blow up the pipeline to interfere with the US dependence on oil. They stop him, have sex along the way, and everyone feels pretty good about themselves.
3 SUSPIRIA
Perhaps it was her creamy olive skin. Perhaps it was her raven hair. Perhaps it was because her husband was gunned down in front of her and her daughter was abducted that made the Punisher pay attention to Suspiria. In The Punisher Red X-Mas, mob boss Vincent Carraciola shoots her husband and kidnaps her child, agreeing to release her only if Suspiria succeeds in killing designated targets on his hit list.
One of the names on that list is Frank Castle. This doesn’t end well for the newly turned assassin as he throws her off a building. She returns some time later, however, to convince him to help her kill the people responsible for abducting an American senator’s son. The Punisher: Bloody Valentine sees the two of them becoming an item, because there’s nothing more romantic than commiserating under the sheets about the loss of everyone you’ve ever loved.
2 ELEKTRA
One day, the Punisher was shooting bad guys the way the Punisher does in Thunderbolts #30, mowing them down with his sniper rifle and living through a pretty good day in the life of Frank Castle. Along comes a foxy Grecian assassin in a spicy red number who manages to kill every criminal he has in his scope before he can.
This frustrates the Punisher, in more ways than one, and the only solution seems to be to ask the lady to dinner. It’s not every day he meets another superhero, much less a beguiling woman, who relishes the kill like he does, but do it Elektra does. And in Thunderbolts #7, they consummate their odd affair amidst a bevy of bullets and bodies, just the way two badass killers would.
1 MARIA
To say that the Punisher got lucky with Maria Castle is an understatement; they had two kids together. But beyond that, she was the love of Frank Castle’s life. It’s interesting to note that of all the ladies that the Punisher has gotten lucky with, Maria was the only one to know him as the real Frank Castle, before the vengeance.
All of the other women may have known his identity (or not, in the cases where he used one of his many aliases), but he wouldn’t have let them in emotionally to any real extent. The only way he could conceivably do anything with them was by continuing to be a callous shell of a man. In fact, he may have felt like it was cheating to be with anyone else, so the only way to take care of his needs was to compartmentalize and get to business.
Did we miss any other lovely ladies the Punisher had relations with? Let us know in the comments section!