Most of the games focus on hope and the internally spirit of good, so I don't commonly think about which Link had it worst. Often times, focusing on that kind of stuff is what leads to a negative depressing spiral, with the depressing game of thrones series coming to mind as the perfect example of misery porn. If I am to be technical, as it's Link reincarnated, he's technically had it rough every time, but if we are to narrow down which version of him had it the worst (or if you're one of those people dead set on each link just being a blood descendent), I would narrow it down to these three:

The hero of legends for A Link to the Past, Link's Awakening, and the Oracle games.
3-1/2 big quests for someone as young as this Link can't be easy to take on. At least in alttp, everyone came back to life, such as his uncle. Then moving to awakening, you have the depressing fact that the island is fake, BUT if it was never real to begin with, was anything technically lost? Then you move to the oracle games, which is the equivalent of the previous 2 quests into one which must be exhausting.

Hero of time from Ocarina of Time and Majora's Mask.
Yeah, I know it's a generic pick, but I'm not referring to the overblown shadow temple portion of the game, although there is merit to counting it for the purpose of the question, as that would be terrifying in real life. Seeing the one soldier die in front of him in the alley, going into termina and seeing people suffer fear every cycle until he manages to save the world (backed fantastically by the world building dialogue that changes on actions and the day revealing their fear and hopelessness), but worst is that he believed he was completely forgotten about due to the time reset for the child timeline, which while partially true for that version of himself, there is some evidence supporting the idea he was known, and he does get some closure by passing his skills to another version of himself.

Link from spirit tracks.
Spirit tracks may be the most unexpected one, but this Link isn't really a fighter. Although he can fight and rise to the challenge, he's an engineer at heart, as selecting the engineer option at the end seems to produce the happier result, and the soldier one implying he really isn't cut out for that life. It wasn't a case of foretold destiny for why he was chosen, he just happened to be the person Zelda asked for help from when everything went down, taking on their journey together.

Was about to post those 3, but then I thought about one more.

Link from Breath of the Wild and Tears of the Kingdom.
From childhood, he had heavy expectations set on him. As a result from the stress he almost never talks (this is explicit in one of Zelda's entries, but he is not mute). The person he was supposed to guard hated him with a passion (although this was resolved later). The worst case scenario happens and the calamity strikes, killing nearly everyone he ever knew. In the process he get mortally wounded and is saved by a long shot, but goes to sleep for 100 years. When he wakes up, he's alone as almost everyone he ever knew had died in battle or of natural causes, and he has no memory. Unlike most journeys where he has a companion, he's forced to go alone. Then after the first adventure, he loses his arm during the second.

Like I said, the main themes of each game comprise of hope. That being said, I doubt I could handle what any of these Links accomplished.

RT: https://poa.st/objects/131475d2-4aae-4438-9d10-6d9119586698
@TrueMasterCole @egirlyuumimain Honestly, it gotta be Breath of the Wild Link, he's the only Link who's actually doomed to failure (even if he eventually gets to partially rectify it), and almost everyone he knew before being placed in the healing chamber is dead by the time he wakes up, unlike OoT Link who gets to reunite with his old friends (though if the Temple Sages really were all killed, that would of course weigh heavily on his heart).

Age of Calamity isn't canon (to BotW at least), so unlike OoT Link there's no reset button to push for BotW Link.
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@ChristiJunior @TrueMasterCole @egirlyuumimain oot link in the child timeline has a pretty shitty time considering he is forgotten entirely despite everything he did. He still gets to experience his childhood and stuff but imagine going through all of that and your story is completely unknown. Though I guess he does get to pass on his knowledge to TP link so he can save the day... But that's still gotta be pretty bittersweet.

Oot link in the downfall timeline just straight up dies, or at the very least fails entirely. He's probably got it the worst.

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