Will Turner, Pirates of the Caribbean movie) of a long movie saga like any good hero was not perfect. He was gallant, he was the best swordfighter in the franchise, and he was a hopeless romantic.
However, Will also grew up a great many years without respectable adult supervision, he spent a good deal of his adult life among pirates and had to deal with a great deal of magic as well. It only makes sense that he would make a few wrong choices along the way.
Seeing His Son
There's nothing wrong with Will, when he can, seeing Henry. It's obviously hard to get to know your offspring when a person can only touch land once a year. However, while a lot of it is Henry's fault, Will seems to see a great deal more of his son than he does of his wife Elizabeth on screen.
Sure, he's been cursed by Davey Jones, but it would have been nice to see Will put in a little extra effort to find a way to bend the rules to his benefit (like his friend Jack used to be so good at).
Trying to Abandon His Son
On the other hand, trying to see his son less was also not the right choice. Literally telling Henry, "You must let me go," and telling him he wants nothing to do with him is a little bit harsh. There must be an in-between way to explain the strange cursed life the family is meant to lead.
Will never had a great father figure role model but that's no excuse for taking out frustrations on his son. They obviously didn't spend enough time together to learn to mitigate some of these feelings.
Getting His Shipmates Killed
In Dead Man's Chest, Will escapes Davey Jones and is rescued by a ship named the Edinburgh Trader. However, the kindness of this captain is rewarded by the Kraken showing up, consuming his crew, and crushing his ship.
While Will certainly didn't get the ship destroyed on purpose, it is his fault that the Kraken shows up and everyone dies. Will tends to lead a lot of people into danger even if he doesn't mean it.
Knocking Jack Out
When Jack and Will go to meet Barbossa on the Isle de Muerta in Curse of the Black Pearl Will, he doesn't fully trust Jack to keep his word and actually help rescue Elizabeth and thus knocks him out and leaves him to Barbossa.
After everything Jack did, and how he never quite said what he meant, but Jack had been helping and had gotten Will to the island, and smacking someone over the head is never really the kind thing to do.
Not Trusting Elizabeth
At the end of Dead Man's Chest, everyone is quite downcast at the loss of Jack to the Kraken. However, Will isn't really as sad about losing Jack as everyone else seems to be.
He's more moping because he thinks Elizabeth is in love with Jack because he caught her kissing Jack before she handcuffed him to the mast and left him behind. The fact that Will couldn't trust Elizabeth, in general, is not a great look on the hero.
Stabbing Jone's Heart
Of course, stabbing the heart of Davey Jones saved Will's life (though he sort of had to live a cursed half-life ever after), but it was still not awesome.
As far as choices went it led to his problematic relationship with his son, his lack of a relationship with Elizabeth, and a job he hated for almost all eternity. Being the new captain of the Flying Dutchman wasn't really what Will wanted, so it wasn't a great choice to take that deal.
Stole a Ship
In Curse of the Black Pearl Will tells Jack that he would do anything for Elizabeth, including die for her. What he has to do first, though, is to steal a ship from the royal navy so that he and Jack can go after the cursed Black Pearl.
The straight-laced pirate hating Will gives up all his morals and steals a ship from the government to go after a woman who isn't even his girlfriend. It should have been clear Will would continue to make morally ambiguous choices.
Betrays Jack
In Pirates of the Caribbean at World's End, Will does worse than just knock Jack out and leave him behind, he actually betrays him to Sao Feng.
Again, Will has irable motives, he, again, wants to free his father, Bootstrap Bill, but he and Jack know each other much better than Will and Bootstrap, and yet Will still throws Jack to the wolves, per usual. The fact that the pair continue to work together throughout so many films is very surprising.
Hunts Jack
Again, poor Jack. Will literally hunts his old ally down in Dead Man's Chest, so that he can rescue Elizabeth from Beckett and the East India Trading Company.
He may have risked his life to save Jack's at the end of Curse of the Black Pearl, but this good deed doesn't last very long when Will is so willing to turn Jack and his com over the instant Elizabeth's happiness is in question.
Wearing That Hat
Will, the good guy and hero, is on full display at the end of Pirates of the Caribbean the Curse of the Black Pearl, when he comes to Jack's rescue at the gallows because he's a pirate but also a "good man".
However, it is a crime against fashion, and a crime against the impeccable beauty of the rest of the film for Will to arrive to do his rescuing in that gaudy hat. Jack's right when he mocks the hat, calling it, "nice," before fleeing once again into the sea.
