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Lots of "frivolous lawsuit" stories tend to be overblown -- what seems like a ridiculous and petty suit turns out to make sense when examined in its proper legal context. But even though no more than 80 percent of the Cracked staff has law degrees, we're pretty sure the following lawsuits -- in which criminals sued their victims -- are about as bad as things get.

Sure, most of them didn't win, but you still have to stand back in awe at the sheer balls it takes to follow through on lawsuits like ...

5
A Man Sues His Hostages for Breaking Their Promise Not to Call the Cops

Gakhan ARICI/Photos.com

We're fond of telling people they should quit while they're ahead. Well, in Jesse Dimmick's case, he was never really ahead, not once. But he still should've quit.

Back in September of 2009, Dimmick was a murder suspect who was running from the police, with some degree of success. Unfortunately for him, the tires on his stolen car were flat due to the police stop sticks he'd run over during the chase. So, needing a place to lay low, he got out and banged on the door of Jared and Lindsay Rowley, a pair of newlyweds. Figuring that if he was going to go on a crime spree, he might as well go all the way, Dimmick took the couple hostage.

Hemera Technologies/AbleStock.com
"Hi! I'm Murderer, and I'll be your host this evening on the Newlywed Game!"

At this point the Rowleys were able to gain Dimmick's trust by feeding him a nutritious and delicious meal of Cheetos and Dr. Pepper. The trio then settled in to watch Patch Adams (no, really), and Dimmick dozed off. The Rowleys called the cops and they captured Dimmick, shooting him in the process. Look, real world criminals aren't exactly Dr. Moriarty, OK?

The Lawsuit:

To be fair, the victims struck first, suing Dimmick for $75,000 in damages. Dimmick, on the other hand, felt that not only should they not sue him, but he was the real victim here. He countersued for $235,000, claiming that they reneged on an oral deal to not call the cops on him.

Hemera Technologies/Photos.com
Dimmick claimed they agreed to hide him in exchange for money and movie reviews.

Dimmick represented himself in court, since no actual lawyer wanted to do so. Shockingly, he lost, since:

- Making someone sign a contract under duress (verbal or written) is, well, totally illegal.
- The "wording" of the contract stated that the Rowleys would not call the cops after he left. Since he never left, they were totally in the right to call whomever they wanted.
- Fuck him.

After the case was dismissed, Dimmick tried again, this time suing the Topeka police department for a cool $435,000 over the gunshot wound he sustained during the attack. He claimed that he suffered from digestive problems, depression, and suicidal thoughts that were definitely unrelated to his new home in jail. He also claimed that he had recurring dreams of girls calling him a "monster" because of his scars. Yes, scars. That's it. Not the murder and kidnapping, no. Just the scars.

The Capital-Journal
"Monster" might have been a term of endearment. Scars are sexy.

Dimmick actually managed to get himself a real live lawyer this time around. And it totally paid off, as he ... still lost. Oh. Well, it was good for the lawyer anyway, who still got paid and all.

4
A Home Invader Sues a 90-Year-Old Man Who Shot Him in Self-Defense

nikamata/Photos.com

One of the most satisfying genres of feel-good news stories are the ones where a young would-be criminal attempts to attack, mug, rape, or kill a really old person, only for that really old person to unleash pure hell, laying a smackdown on the ungrateful whippersnapper that they will never forget. One of the quickest ways to ruin such an awesome story is for the whippersnapper to then turn around and sue the old person for beating and/or shooting the living shit out of them.

BananaStock/BananaStock/Getty Images
They beat us in strength and agility, but the elderly are no match for our skill with paperwork.

Such is the case of Samuel Cutrufelli, a drug addict who, in January 2012, decided to solve his woes by finding a random home, kicking the door off its hinges, and ransacking the place for valuables. Cutrufelli soon learned that Jay Leone, the 90-year-old owner of the home, was present at the time. Taking him to be a mere feeble-minded nigh-centenarian, Cutrufelli took Leone hostage and ordered him not to move.

Leone, however, was a World War II veteran and former deputy sheriff, and he was incredibly uninterested in complying. In typical nagging-old-people fashion, Leone repeatedly pestered Cutrufelli about having to use the bathroom. Cutrufelli, deciding that witnessing an old guy shit himself was not how he wanted to spend his afternoon, allowed him to go. Shortly thereafter, Leone returned from the bathroom with a .357 revolver, pointing it right at the burglar. Cutrufelli, not backing down, opened fire on Leone and hit him in the jaw.

Jupiterimages/Photos.com/Getty Images
Leone had taken the gun from the toilet tank. He'd left the cannoli; he had diabetes.

At this point the old man came to his senses and ... actually no, he totally fired back. Cutrufelli, finally remembering that his spirit animal is a scaredy cat, begged Leone to spare his life, pleading, "Don't kill me, I've got a daughter!" Leone, being a kindly old gentleman at heart, responded by emptying his weapon in him anyway. He even provided a classic line for the movie about his life that desperately needs to be made: "Fuck you! Pow pow pow pow!"

Despite being shot three times, Cutrufelli still rushed Leone and pinned him to the ground. He grabbed Leone's gun, put it to the old man's head, pulled the trigger, and ... found it was out of bullets. Cutrufelli resorted to Plan B: He ran out the door, called the police, and claimed that he had shot himself. He was then taken to a hospital and arrested right on the spot, because it turns out calling the cops to tell them you shot yourself makes no goddamned sense.

The Lawsuit:

Speaking of not making sense, Cutrufelli later sued Leone, claiming the old man had "negligently" shot him, and that he did so because he was jealous of Cutrufelli for visiting one of the ladies in Leone's house. Since Leone, you know, hit him exactly as he intended to do, what he did was actually the exact opposite of "negligent." Also, since Cutrufelli had fired the first shot AND tried to rob the man AND held him hostage, the judge bought his argument even less.

Frankie Frost/Marin Independent Journal
Cutrufelli remained optimistic about his final "veterans suck" argument.

Not only was the lawsuit thrown out, but Cutrufelli was quickly sentenced to 86 years to life, the life part tacked on just in case he lives to be 120 years old.

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3
A Man Steals from His Job and Sues His Boss for Way More

Peter Lawson/East News

Admittedly, it wasn't exactly a Bernie Madoff-scale scam: British floor fitter Mark Gilbert decided to make a check from the business out to himself, just to see what would happen. Well, what happened was his boss, Simon Cremer, found out and flipped his shit. While he could have merely called the police, he instead decided to take the "shame and humiliation" route. Cremer and Gilbert marched to the police station, with Gilbert forced to wear a cardboard sign around his neck that read "THIEF I Stole 845 POUNDS AM ON MY WAY TO PoLice Station."

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The fabled "Queen's English" that we all emulate.

Gilbert admitted the crime to the authorities and was let off with a warning. Cremer did not pursue it any further and was content to fire Gilbert for being a dirty thief.

The Lawsuit:

Gilbert, however, was not satisfied. He sued Cremer for lost wages, trauma, mental damage, and a pathological fear of all things cardboard. Now, we're aware that it's not actually legal for citizens to go around imposing their own public shaming on criminals, as that sort of thing can go wrong in a hurry. But that's not what the lawsuit was about. It was about Gilbert having a shitty life after being publicly humiliated for stealing and then getting fired. In short, he stole from his boss and now wanted to sue his boss. We all know by now how such a stupid piece of frivolity will inevitably pan out ...

The Express

The fuck? HE WON? Yes, Gilbert ended up receiving 13,000 pounds from Cremer, over 15 times the amount he originally stole. Admittedly, the victory came after Cremer agreed to settle out of court, but he very likely knew he was screwed, what with the whole "false imprisonment" thing Gilbert's lawyers would almost certainly bring up time and time again. Plus, once he realized it would have cost him over 25,000 pounds in legal fees just to fight this thing, he decided that tapping out and letting the thief win was the only logical choice.

Not that he liked having to do it. Cremer was quoted as saying "I think it's absolutely disgusting that he was even able to sue me ... he stole from me, yet he is the one walking away with the money." Such a sore loser.

2
A Man Sues the Widow of the Man He Murdered for Not Letting Him Go to His Preferred Jail

Darrin Klimek/Digital Vision/Getty Images

Larry Shandola is the living embodiment of the phrase "With friends like this, who needs enemies?" Way back in the day, Shandola was friends with Robert Henry, and the two even got chummy enough to start a joint business venture together. In 1995, said venture sadly failed, and Shandola reacted in the most mature manner he knew how: by shooting Henry to death with a shotgun.

Jupiterimages/Photos.com/Getty Images
"Now, the failed venture is mine and mine alone. I'm rich!"

Shandola was sentenced to 31 years in prison, so Henry's family figured that would be the end of their nightmare. But 18 years after murdering Henry, Shandola decided the time was right to sue Henry's family.

The Lawsuit:

Shandola sued Henry's widow, Paula, and three others for $100,000 apiece.

His reasoning made every last bit of sense in the world -- he wanted to transfer to a Canadian prison, since that's where he's from. Henry's widow, Paula, had written a letter to the court asking that his request be denied.

National Post
"We couldn't save my husband from this madman. But I can save Canada."

In Shandola's lawsuit, he claimed that Paula Henry invaded his privacy and intentionally caused emotional distress by not allowing him to serve his sentence in his home country. This is understandable -- Shandola was locked up in Washington State, which is right on the border of Canada. He probably smelled the maple syrup in the air and got nostalgic. Also, we're guessing he assumed that the four walls he'd be staring at every day in Canada would be prettier and softer to the touch than the four walls he was staring at every day in Washington.

The judge, as judges are wont to do in these situations, dismissed the case. However, he didn't just dismiss it; he ordered Shandola to pay Paula Henry, and the three others, $10,000 apiece, or $40,000 total. That might seem like an awful lot to ask of a guy who hasn't had a job in close to 20 years, but in cases like this, it's the thought that counts.

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1
A Man Kills a Child Riding His Bike, Then Sues the Child's Parents

cnrn/Photos.com

David Weaving was driving around on April 26, 2007, when he struck 14-year-old Matthew Kenney, who was riding his bike at the time. The collision proved to be fatal, and Kenney died shortly thereafter. As a result, Weaving was sentenced to 10 years in prison, avoiding more time since he was actually sober during the accident (quite the rare feat for a man with five drunk driving arrests on his record, four of which resulted in convictions).

Medioimages/Photodisc/Photodisc/Getty Images
"I just wanted to prove I could be dangerously irresponsible without alcohol."

The boy's parents, deciding that 10 years in prison wasn't enough for a guy who probably shouldn't have had a license in the first place, sued Weaving for criminal negligence, and $15,000. Weaving, for the second time proving that he didn't need alcohol to be a douche, responded with a $15,000 countersuit of his own, which he wrote by hand (probably in crayon).

The Lawsuit:

In the filing, Weaving accused the parents of negligence, which is basically the legal version of "I know you are, but what am I?" His rationale: Matthew Kenney was not wearing a helmet, and his parents were to blame for allowing him to ride without one. Going by that logic, he should've also sued for their daring to conceive him in the first place. After all, if he had never lived, he never would've been killed.

ABC
He also claimed Kenney's inheritance as his own, having "fairly bested the boy in a duel."

In the suit, Weaving also claimed that Kenney jumped his bike off a ramp and landed in the middle of the road like he was Evel Knievel. Also, Kenney did this while suddenly appearing in the middle of a foggy road, because he was such a bastard like that. Although it's actually quite understandable that Weaving couldn't see Kenney, especially since he was going close to 90 miles per hour at the time. Shit gets blurry by that point.

The judge ultimately stated that, while he agreed with Weaving's right to sue, he also believed that Weaving was a goddamned moron, and determined him to be recklessly negligent after all. What do you know, the system works.


Matt Pass is a standup comedian. Follow him on Twitter if you only liked the first 140 characters of this article, email him at mattpasscomedy@gmail.com, or learn about his weekly Philadelphia comedy show.

Related Reading: This article was kind of a bummer. Pick your mood up with some cases of criminals instantly repaid by karma. Watch that mugger get hit by a bus and bask in the glow of random justice. Then read about badass criminals caught in embarrassing ways. Eric Rudolph- a real-life terrorist version of Rambo, wound up arrested while dumpster diving in the wee dawn hours. Last, boost your faith with a look at ruthless criminals who turned good when no one was looking.

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