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Harsher In Hindsight / Star Wars Legends

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    Comic Books 
  • Legacy:
    • Cade blaming the name of Skywalker as the cause behind the family's Trauma Conga Line, which unfortunately is a problem that persists in the Sequel Trilogy.
    • Luke's Force Ghost berating Cade to tough it out through hard times and never lose hope and abandon his burdens, after his Sequel Trilogy counterpart did just that in The Force Awakens and The Last Jedi, which many consider Canon Defilement. Some people put them together. The Rise of Skywalker may have ended up turning this into Heartwarming in Hindsight by showing that Luke did ultimately develop the same attitude as a Force Ghost that he does in Legacy, convincing Rey not to give up like him and finish saving the galaxy.
    • A series about distant descendants of the Skywalker/Solo family can be a bitter pill to swallow after The Rise of Skywalker wiped out the entire family only one generation after the OT trio, and 102 years before this series kicks off. If there's any consolation, though, we at least have Rey Skywalker…
    • At the time, it was perceived as a rather sad Happy Ending Override that a new Empire would rise and conquer the Republic about a century after the peaceful declaration of The Hand of Thrawn. The sequel trilogy would reveal that the peaceful galaxy shown at the end of Return of the Jedi didn't even last forty years before an Imperial successor burned it to ash.
  • Republic: One episode has Mace Windu join up with Agen Kolar, Saesee Tiin, and Kit Fisto to take down a group of bounty hunters that had been accepting marks on Jedi. This is the exact makeup of the team that gets creamed by Sidious in seconds in Revenge of the Sith, and even worse, the head bounty hunter gets taken down in an act of betrayal by a foster family figure, in an almost exact inversion of Anakin's betrayal of Windu and the Jedi Order to save Palpatine and his wife. Impressively, this particular comic was published over a year before Revenge of the Sith was released, and given the vast number of Jedi to pull from, that this exact matchup would happen is a pretty remarkable coincidence.

    Infinities 
  • Tag and Bink:
    • Back in the first issue, Tag and Bink were trying to escape to Alderaan to get away from the chaos of the Galactic Civil War, only to witness it being obliterated. Then the prequel "Revenge of the Clone Menace" reveals that Alderaan was Bink's homeworld.
    • "Revenge of the Clone Menace" sees Jango Fett going into a Jedi-killing blood-frenzy and trying to kill Tag and Bink upon hearing the words "Order 66" at Dex's Diner, which gives a comically dark implication that the Jedi Purge was the result of the Clone Troopers inheriting an innocuous mental trigger from their source rather than a secret order plotted by Darth Sidious. Years after that comic released, The Clone Wars revealed that the actual Order 66 works in an almost similar fashion with the clones as a result of mind-control chips planted in their brains before they are even born. Nala Se, the Kaminoan scientist who was involved at the least in implanting the chips in the Clones' brains, even tried to claim that these chips were used for suppressing aggressive tendencies inherited from Jango.
  • Star Wars Tales: George R. Binks, Jar Jar Binks' father, attempting suicide as a result of being driven mad by his son's antics can become a lot more uncomfortable after Ahmed Best revealed that he once contemplated suicide after facing a wave of harassment for his role as Jar Jar.
  • In Phineas and Ferb: Star Wars, when two Rebel Soldiers find R2-D2 without the disc containing the plans for the Death Star, one of them suggests they "blame Jar-Jar", to which the other says that Jar Jar retired "years ago". Canon would reveal what would happen to Jar Jar in Aftermath: Empire's End and let's just say he would have preferred retirement to what happened to him in the novel (kicked off the Senate for being the one to give Palpatine emergency powers, exiled from Otoh Gungan again and lives out his days in a refugee center on Naboo as a clown, suffering great guilt for what he did.)

    Literature 
  • Black Fleet Crisis:
    • Anyone who tries to read the series now knows that Luke's mother is dead, and thus his quest is completely for nothing. Worse yet: R2-D2 knows it is and could have saved Luke a lot of grief; if he wasn't already "recruited" by Lando on his own wild bantha chase and thus out of contact.
    • Senator Peramis and his desire to de-militarize the Republic becomes this due to the new Disney canon timeline, in which such policies were actually implemented in the New Republic, with the Imperial Remnant following suit after signing a treaty with them. This proves to be utterly disastrous as the First Order, composed of Imperials hiding in the Unknown Regions who did not abide by said treaty, were able to establish utter military dominance and even destroy the Republic capital with a devastating system-killing superweapon, and only Leia's rag-tag Resistance is able or willing to put up any sort of real fight.
    • Han's line early in the book about him not being surprised that Luke wouldn't be found on a deserted island in the middle of nowhere after his disappearance.
  • Clone Wars Gambit: At one point, Ahsoka thinks in Wild Space that at least she's Anakin's apprentice, and no one can take that from her. Come the fifth season finale of Star Wars: The Clone Wars... Of course, after Revenge of the Sith, being Anakin's apprentice isn't exactly something to be proud of, anyway.
  • The Han Solo Adventures: In Han Solo's Revenge, Chewbacca roars in anger and disgust when he realizes that he and Han have been hired to transport slaves. The context of the book doesn't imply anything more than a simple moral objection to slavery, but later EU works, as well as Solo, would reveal that Chewie has spent time in chains himself.
  • The Han Solo Trilogy:
    • Han makes many smuggling friends, especially in The Hutt Gambit. Of all these friends only Chewie, Roa, Shug, Jarril, and Salla don't end up betraying him in later years.
    • The Battle of Nar Shaddaa in the climax of The Hutt Gambit is one of the cornerstones of the trilogy, gets a lot of buildup, and spends time talking about how the ragtag smuggler fleet is invested in protecting the millions of people (refugees, immigrant communities with many families, street kids who grew up there, etc.) who have no way to evacuate before the Empire's planned razing of the moon. In New Jedi Order, the Yuuzhan Vong launch a more successful attack on Nar Shaddaa that certainly kills many of those same people Han and his friends were defending.
  • Jedi Academy Trilogy: Luke Skywalker sets up a training academy to instruct the next generation of Jedi in the ways of the force... only to see one of his students fall under the influence of a master of the dark side and go on a rampage while Luke is incapacitated. In this trilogy, things turned out mostly okay in the end for Legends Luke (with a lot of caveats). As seen in flashbacks in The Force Awakens and The Last Jedi, a similar scenario resulted in the destruction of Canon Luke's academy and death of all its studentsnote .
  • The Jedi Path: A section discussing the temptations of the dark-side has an illustration of a green-skinned, female humanoid Jedi, looking worriedly in to a mirror, an evil, red-skinned version of herself beckoning in the reflection. She looks similar to Barriss Offee, Luminara Unduli's padawan who, near the end of season five of Star Wars: The Clone Wars, really did fall to the Dark Side of the Force.
  • Legacy of the Force: Back in the New Jedi Order series, Leia had a depressing vision of Jaina and herself telling Jaina’s kids about their heroic late aunt Mara. The vision seemed to have become irrelevant when Mara recovered from her illness, then 16 years later, Jacen became Darth Caedus and killed Mara.
  • MedStar Duology: Every moment where Barriss worries about the temptations of the Dark Side feels sadder after she ends up murdering many fellow Jedi in the Filoni cartoon.
  • New Jedi Order:
    • Chewbacca's death, while a Tear Jerker before, has been made worse after The Force Awakens, where in the new canon, Han and Chewie effectively switch places, with Chewie watching helplessly as Han is struck down. Chewie was also the only one of the original hero quartet to be killed in Legends. As of The Rise of Skywalker, he is the only one still alive.
    • Watch Jacen Solo, especially earlier in the series, opposing Luke in forming a Jedi Council, and his generally low opinion of politicians in general, and his belief that a Jedi should be guided by their own relationship with the Force and knowledge of light and dark. Then recall Anakin Skywalker's thoughts on politics in Attack of the Clones, and what Jacen ultimately becomes in Legacy of the Force...
    • In 1998 (the year Vector Prime, the first book, was published), the idea of a group of invading fanatics following a twisted version of a generally benevolent religion who are unafraid of death or using self-destructive or suicide tactics threatening the galaxy was probably seen as just another Star Wars story. Three years later (at about the midpoint of the story arc), a group of fanatics following a twisted version of a generally benevolent religion used a suicide tactic to put a hole in the middle of New York City.
    • Near the end of "Onslaught", Jacen and Anakin are talking and getting philosophical.
      Jacen: Look, one thing, no matter what we did at Dantooine, I was proud to have you at my side. I don't know what I'll be in the future, Anakin, but I know you'll be a great Jedi Knight. I have confidence that you will succeed, no matter what life throws at you.
      Anakin: Are you really Jacen, or some Yuuzhan Vong in an ooglith masquer?
      Jacen: For now, I'm Jacen Solo.
      Jacen: [thinking] What I'll be in the future, however, is anyone's guess.
    • Mara Jade's illness becomes a lot harsher after Shannon McRandle, the model behind Mara in Star Wars trading card games (and whose likeness has been used for Mara since), was diagnosed with cancer in 2013 and several other debilitating conditions including ankylosing spondylitis.
    • Jacen Solo's Day in the Limelight being titled Traitor feels a lot harsher after his Face–Heel Turn.
    • The scene in The Final Prophecy when one of Wedge's subordinates breaks free of the plan, jeopardizes the mission, and ignores his CO's orders in order to do what he thinks is right becomes this after The Last Jedi, when the same thing happens (and became very contentious). However, in this case, the audience sympathizes with and trusts Wedge, rather than the hotshot pilot.
  • Shadows of the Empire: Leia's Heroic BSoD after Fett escapes with Han again. Sure, most readers have already seen Return of the Jedi—which provides a positive Foregone Conclusion to mitigate this... But in The Force Awakens, Han is Killed Off for Real—resulting in Leia being even more devastated.
  • Tales of the Bounty Hunters:
    • In "The Last One Standing", part of the record 5 million credit bounty that Boba Fett takes by capturing Kardue'sai'Malloc alive goes to cancer treatments, which his narration says have been bankrupting him. Medical bankruptcies and the general high cost of US healthcare would go on to become a major political issue in the United States in the ensuing decades.
    • Jabba gives the enslaved Leia to Boba as a reward, but Boba refuses because he believes rape and having sex outside of marriage are wrong. In Star Wars Blood Ties, Boba strained his marriage with Sintas because he initially blamed her for getting raped by his boss, though he later killed him to avenge her at the cost of getting kicked out of the Journeyman Protectors and exiled, destroying their marriage.
  • The Thrawn Trilogy:
    • Han and Lando have a joking exchange about a particularly rough landing of the Falcon, to which Han retorts that at least the sensor dish is still there. Lando replies that next time, he'll take down the shield while Han flies the Falcon down the Death Star's throat. Han muses that it really isn't all that funny, since if Thrawn manages to get back enough of the Empire's old resources, he might just try and build another of the damn things. Fast forward just a hair, and the Star Wars EU becomes positively littered with superweapons, both leftovers and new constructions. (And cue the Take That! to this era of EU in Hand of Thrawn where it's explicitly stated the only weapon Thrawn ever needed was information.)
    • Thrawn's treatment of the Noghri becomes this after Outbound Flight, where he, as a young officer, expresses some distaste for slavery.
    • In The Last Command Han and Leia start trusting Mara after she risks her life to save their newborn children Jacen and Jaina from being kidnapped. Years later, Jacen would pull a Face–Heel Turn and kill Mara. Oddly enough the irony of this was never pointed out in the latter book.
    • C'baoth's claim that the Jedi were condemned and turned on by the galaxy as a whole when the Emperor was wiping them out is presented like just another part of his clone madness, but the prequels established that was more or less exactly what happened.
  • X-Wing Series: Isard's Revenge (published 1999) has several rather eerie parallels with the Iraq War: a highly controversial invasion of a neutral power to depose a dictator for political reasons,note  publicly spurred on by supposed evidence of a bogus superweapon.note 
  • Young Jedi Knights: Jacen and Jaina are tricked by Sith into fighting each other to the death (each is forced to believe that the other is actually an unknown Sith), but recognise each other just in time. In Dark Journey, during the Yuuzhan Vong War, Jaina has a Force vision of these events, wherein she does kill Jacen by mistake. Much later, in Legacy of the Force series, they do fight again—and this time Jaina does kill Jacen, who was now really a Sith, but considered surrendering and repenting.
  • There’s a quiz book called the Diplomatic Corps Entrance Exam that has a lot of multiple choice questions about the movies and early books. One question asks which of Luke’s students fell to the dark side. The correct answer at the time was Brakiss, but another answer choice listed is Jacen Solo, who of course also fell later on.

    Radio 
  • Radio Dramas: The mental tortures Vader puts Leia through in lieu of using the torture droid are much harsher in light of knowing that he is her father. For one, there's a point when he claims to be her father (Bail) and needing her information, which is also the one time in her life he speaks kindly to her. For two, there's a scene where he makes her believe she's had limbs cut off and she is burning alive and dying - Mustafar much? It also contains an element of Historical Irony as, at the time, neither Vader nor the audiencenote  knew that Vader was Leia's birth father.
  • During the victory celebration at the end of Return Of The Jedi, Leia teases Han by joking to Luke about Han planning to "make [Luke] an uncle". Considering all the things Luke's nephew would go on to do...
  • While the Emperor is torturing Luke to death and Luke begs his father to save him, Palpatine arrogantly sneers, "He is my slave—not your father." This is what finally gets Anakin to turn on his master and save his son. When this was broadcast in 1996, it's plain that being compared to a slave was what finally got Anakin to realize just how much he was being used by his cruel master - nobody at the time had any clue that Anakin grew up under the dehumanizing misery of slavery, along with his beloved mother; something the Emperor knew full well. Unless George Lucas just happened to clue in Brian Daley on something he was writing for an early draft of The Phantom Menace, this was one hell of a coincidence that makes the resolution even more powerful.

    Video Games 
  • Dark Forces Saga: In Jedi Academy, if Jaden goes down the Dark Side, he'll kill Rosh and multiple Jedi students on his way to the tomb in Korriban. Much like how Kylo Ren had butchered Luke's students before The Force Awakens in the new canon. The ending compounds it while Luke in the game supports Kyle's decision to find and try to bring Jaden back to the light, the new canon has the ordeal become a Despair Event Horizon for Luke.
  • Empire at War: Late in the Forces of Corruption campaign, Tyber Zann threatens to commit genocide on the Witches of Dathomir if Silri were to lie to him again or betray him. In the Star Wars: The Clone Wars episode "Massacre", almost the entire Nightsister clan (which Silri belongs to) gets annihilated on Count Dooku's orders, two decades before Forces of Corruption would take place. While the Nightsisters would have eventually recovered in Legends, they don't get that luxury in canon and the Dathomirians are a Dying Race as a result.
  • The Force Unleashed: That scene where Starkiller kills Han Solo with his lightsaber at the end of the Han/Chewbacca fight sure does get a lot more depressing after what happened to him in The Force Awakens.
    • Even worse, Starkiller also kills Princess Leia shortly after killing Han, which becomes even far harder to watch after Carrie Fisher's death, which also drastically affected Leia's planned role for The Rise of Skywalker, forcing them to kill her off, effectively making the Dark Side ending of both games come true.
  • Knights of the Old Republic: All of it after you've played Star Wars: The Old Republic.
    • Every victory you or your party members accomplish is used for target practice or a sick, twisted joke. Even your Player Character ends up charging in on an ill-prepared "plan" to stop the Sith Emperor and loses, is subject to Mind Rape by the Sith Emperor for 300 years, the Sith come back and curb-stomp an unprepared Republic anyway, and Revan ends up an insane Omnicidal Maniac that has to be put down like a rabid mutt by the Imperial faction, gets a Literal Split Personality and the half that refused to stay dead gets killed by what amounts to a dark mirror of Revan's party from the game (especially true on a Warrior with Vette, a Knight with Teeseven, or anyone else with HK-51.
    • During the Sunry murder trial sidequest, Jolee claims that Jedi don't murder even the Sith in their sleep. In the main canon's The Last Jedi, Luke Skywalker, in a moment of weakness, considered murdering Ben Solo in his sleep out of fear that he might have been corrupted by the Dark Side. While he ultimately chose not to go through with it, him attempting to do it at all ended up creating Kylo Ren and destroying the rebuilt Jedi Order, and Luke feels very disgusted by his own behavior.
    • A Dark Side run will force you to kill Mission. Flash forward to Star Wars: The Old Republic and Knights of the Eternal Throne, and choose to save Torian Cadera. Vette - who is Mission in all but name - will then be the party member executed by Vaylin.
  • Knights of the Old Republic II: The Sith Lords: Kreia's reason for wanting to destroy the Force is because she sees it as nothing more than a repeating war that never ends. The Sequel Trilogy canonically proved her right.
  • LEGO Star Wars:
    • Ahsoka Tano and Barriss Offee chatting it up in The Clone Wars, considering what happened between them later in the show the game is based on.
    • Remember that nice little bonus level in the original Lego Star Wars where you got to play as Darth Vader slicing his way through crowds of LEGO rebels? Well, Rogue One brings that to life in horrifying detail more than a decade later.
  • Maul: The game centering around a clone of Maul is this in light of Maul's character arc in Star Wars Rebels and Season 7 of Star Wars: The Clone Wars, where it's ultimately revealed that after everything he's been through, he just wants to die.
  • The Old Republic: A number of player choices can fall into this trope or Player Punch, depending on how you look at them. Republic and Imperial characters alike can do things to the other side that can really hit hard if you have played both factions.
    • On the Republic side, for example, witnessing the brutal Ulgo experiments on the Killiks and choosing to continue them for House Organa will likely make those with Imperial Agent characters squirm. One of the most beloved Agent companions, Vector Hyllus, is a Joiner, and his character and story delve deep into beauty of the Killiks and their struggle to be recognized in the Empire.
    • Meanwhile, on the Imperial side, players, especially dark side ones, can do downright vicious things, the same kinds of actions that, when seen from the Republic's POV, can often personally traumatize Republic player characters, companions, and allies. For example, dark side Sith Warrior players hunting down and brutally murdering Jasea's parents or sending them to be tortured by Baras can be pretty haunting for those same players as Jedi Consulars when you discover Nadia's father tortured and murdered by an insane Sith Lord. Likewise, dark side Sith Warriors killing an unconscious Xerender in front of Wyellet can be unnerving when those same players experience Darth Angral killing Orgus Din right in front of them on the Holonet in the Jedi Knight storyline.
    • In combat, Vette may yell to the Sith Warrior that "if I die, I'm haunting you", In Knights of the Eternal Throne, Vaylin will kill her depending on if the Outlander choose to save Torian rather than her. Likewise with another joke made in an earlier chapter A Female Bounty Hunter gets a good luck wish from Torian in the form of Ib'tuur jatne tuur ash'ad kyr'amur. (Mandalorian for: "Today is a good day for someone else to die.") If you choose to save Vette, that "someone else" is Torian.
    • A real-world one, sadly. The Life-or-Limb Decision decision the Sith Warrior imposes on Tremmel became this when it was announced that Tremmel's voice actor (Paul Darrow) had to have his legs amputated to save his life. And despite the amputation and the best efforts of the doctors, he passed soon after.
  • Star Wars Chess: Luke's uncharacteristic beheading of a Tusken Raider becomes this when you see Anakin do the same to the first of a whole settlement of Tuskens as his Start of Darkness in Attack of the Clones.

    Western Animation 
  • Clone Wars: Watching Barriss Offee defend a Jedi temple as it's being bombed becomes hard to stomach knowing that she would grow disillusioned with the Jedi over time and would go on to bomb a Jedi temple herself in Star Wars: The Clone Wars.
  • Droids:
    • Thall is shown wielding a lightsaber in the very first episode. But the show takes place only a few years after Revenge of the Sith, meaning he must have gotten it from a recently slain Jedi. Alternatively, Thall is a young Jedi who's been hiding out for the past few years, and was probably slain himself offscreen.
    • The entire tie-in comic series could qualify because New Jedi Order has that the Yuuzhan Vong destroying Hosk Station and Kalarba. By dropping Hosk Station onto Kalarba!


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