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The Most Terrible Things Jack Sparrow Has Ever Done

There isn't a more beloved character in all of the "Pirates of the Caribbean" films than our leading man Captain Jack Sparrow, even if he's always out for himself. Whether it's because we actually see some good in the occasionally heroic pirate or we just love Johnny Depp's fabulous portrayal, people have defended some of Jack's most heinous deeds for a long time — mostly because everything happens to work out alright in the end. In any case, Captain Jack may not be as good a guy as you remember, and upon further inspection it's clear that he's actually pretty terrible at times.

With a sixth "Pirates of the Caribbean" film apparently underway, and one that might not feature our elusive captain, it's as good a time as any to reflect on the mistakes of the past so that our favorite pirates can thrive in the future. While it's no doubt that we'll continue to cheer Captain Jack Sparrow on each time we watch his story unfold, we can't ignore some of these terrible choices he made along the way.

Ruined Angelica's life more than once

"Pirates of the Caribbean: On Stranger Tides" is a bit of a mixed bag. The film ups the Jack Sparrow comedy to 11 with no Will Turner or Elizabeth Swann to ground him or the story, making it the odd one out among the series. But regardless, there's no denying that what Jack did to his old flame Angelica nears his top of the list of sins. The daughter of Blackbeard, Angelica forsook her father's life of piracy, clung to her Catholic faith, and decided to become a nun. Before taking her vows, Angelica was seduced by a young Jack Sparrow, who took her away from the nunnery and brought her into a life of crime. Nothing like good times with a pirate to pull you away from your faith.

After their time together, plagued with continual betrayals (it's kind of Jack's thing), Angelica was left heartbroken by Jack, with no way back to her old life. Because of this, she eventually joined her father's quest to find the Fountain of Youth, which Jack also ruined by contributing to the death of Blackbeard (which, to be fair, did save Angelica's life). By the film's end, rather than apologizing for his mistakes or taking her back to civilization, Jack strands Angelica on a deserted island, ruining her life yet again. But hey, at least she was left with his voodoo doll to keep her company.

Double-Crossing the British

Speaking of betrayal, if there were an award for most people betrayed in a single film, Jack Sparrow would certainly be a contender. No matter who you are, your relation to him, or how aligned you think your goals might be, Jack will always find a way to twist the scenario to his own benefit at your expense. In the first film, "The Curse of the Black Pearl," Jack convinces Commodore James Norrington to engage with the pirate Hector Barbossa and his men on Isla de Muerta in a "surprise attack," only to immediately reveal said-plan to Barbossa in exchange for his own life.

This results in a slaughter of many of Norrington's men as Barbossa's skeleton army takes them out one by one, even nearly overtaking their ship, the HMS Interceptor. Much of the blood spilled during this attack is directly the result of Jack's meddling and betrayal, but somehow it was all a part of Jack's master plan. Soon after, Jack and Will Turner lift the skeletal curse and Barbossa's army are returned to their normal human forms — just in time for the British to overtake the pirates, sparing the rest of their lives. This little stunt causes Norrington to send Jack to the gallows, and although he escapes (with the help of Will and Elizabeth), it's certainly not because he was innocent.

Sending Will to Davy Jones

If "Pirates of the Caribbean: Dead Man's Chest" taught us anything about Jack, it's that he's definitely not an innocent man. After meeting back up with Will Turner, Jack sends the boy off to the Flying Dutchman to join Davy Jones' crew in an effort to save his own skin. While Jack mostly wants to use Will's captivity to help locate the Key to Davy Jones' Chest, he has no problem telling Jones that Will's newfound life of servitude should count towards his own debt with the cursed pirate legend, squaring everything up "neatly."

Of course, nothing is quite so easy in the "Pirates" universe. Jones doesn't accept Will as Jack's only form of payment, but Jack refuses to fight for the boy, instead leaving him in the tentacled hands of the mythic pirate. This might cause more problems for Jack later than it was worth (Will decides to fight Jack for the Chest, wishing to use it to free his own father from the Dutchman), but it wouldn't be a Jack Sparrow plan without a few setbacks. Either way, Jack is a pretty terrible friend and what he did was inexcusable.

He's a straight-up murderer

Although Jack handed Will over to Davy Jones, it didn't quite settle his debt. Jones tasked Jack with collecting 99 more souls to square their deal, and Jack accepts the deal without hesitation. Sure, everyone in the "Pirates" movies has at least a little blood on their hands, but Jack doesn't think twice about going the extra mile. While in Tortuga, the pirate capital of the Caribbean, Jack tries to collect as many "undesirables" as possible (including a disgraced James Norrington), hoping to hand them all over to their deaths. It's pretty heartless, and while Jack doesn't actually meet his quota, it's worth noting that he fully intended to.

This isn't the only period where Jack's been a mass murderer, though. Besides deadly combat, Jack also helped the pirate Blackbeard massacre a group of mermaids in "On Stranger Tides." Of course, mermaids, much like pirates, aren't actually innocent creatures (they do lure men to their deaths after all), but Jack seems to have no real problem with the slaughter of these mythical creatures — or anyone else for that matter. Death doesn't bother Jack all too much, unless it's his own.

Jack almost allows his crew to be eaten

Earlier in "Dead Man's Chest," Will finds Jack and his crew run aground on a tribal island somewhere in the Caribbean. On this island, Jack somehow talked his way into becoming the tribe's leader, their "god." What Jack didn't know was that the tribe planned to eat him by the end of their ritualistic ceremony. He eventually escapes, but he seems to be fully aware that the tribe was saving Will and his crew for a fleshly feast.

When Will meets up with Jack, rather than telling Will to liberate the crew and then help free him from the tribe's makeshift grill, he begs Will to save him only, with no thought for the crew at all. Now sure, Jack was as much a prisoner of the cannibal tribe as anyone, but there's no doubt that when Jack and the crew first arrived on the island, Jack could have convinced the locals not to lock up his friends (especially if he is their "god"). Knowing Jack's inherent selfishness, it's clear he was only thinking of himself, and if Will hadn't arrived, there's no telling what would have happened to the crew.

Trying to romance Elizabeth from under Will

A recurring thread through the original "Pirates of the Caribbean" trilogy is that Jack has a bit of a crush on Elizabeth Swann, and for good reason. Elizabeth is strong, confident, fearless, and an all around catch — which of course means that she's not the type of girl who would be interested in someone like Jack. Knowing full well how Will feels about her, Jack attempts (on multiple occasions) to take advantage of and seduce Elizabeth, including getting drunk with her, so that he might "woo" her into his arms. It's pretty gross.

Naturally, Elizabeth is a bit too smart for Jack, and she actually uses her feminine prowess against him at the end of "Dead Man's Chest" so that the crew might escape the Kraken's clutches. After all, it was only after him, so why should the others have to also die? By the time Jack sees Elizabeth again, he's increasingly more distrustful of her, but eventually comes around and supports her as the new "Pirate King" when the chips are down. Still, the way he pursues Elizabeth, especially when she's clearly spoken for, is a bit icky and is just another glimpse into Jack's constant womanizing.

He was willing to sell out all other pirates

After being resurrected in "Pirates of the Caribbean: At World's End," Jack quickly makes a deal with Lord Cutler Beckett, the governor of the East India Trading Company. Beckett wants information about the Brethren Court, the Pirate Lords, and the Nine Pieces of Eight. Jack does him one better: He tells Beckett that he'll lead him to Shipwreck Cove — the meeting place of the Pirate Lords. When at Shipwreck Cove, Jack plans to get all of the pirates to go to war so that they might be annihilated by Beckett and his vast armada. Seems like a shady thing to do.

Why would Jack do this? Not only to square his debt forever with Davy Jones, but also to become the "last pirate" and sail the seas unhindered by forces like Will, Barbossa, or the other Pirate Lords who might have it out for him. With no regard for anyone but himself, Jack makes this deal with Beckett and slowly leads him to the meeting place of the pirates (which includes sending Will to Beckett and Davy Jones yet again). At the end of the day, Jack helps Will, Elizabeth, Barbossa, and the others defeat Beckett and Jones for good, but his motives along the way seem pretty sketchy.