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AC97
Lunar Supporter - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).
Non-Fungible Trixie -
My Little Pony - 1992 Edition

Especially since Chrysalis never seems to learn from her past mistakes anyway.
 
Yep. Chrysalis blames her losses on the heroes “cheating,” when she’s orchestrated her own defeat numerous times, by keeping her back turned at a critical moment in her debut, to how she just didn’t bother in S6 to kidnap and replace Starlight, which started a chain of events that caused her demise.
 
With a being like her, she cannot for the life of her take responsibility for her failures. Her ego pathologically prevents it.
 
Chrysalis cannot win a fight without surprise and/or a power advantage on her part (both of which were the case with Celestia in S2). She’s never learned much finesse in her fighting, because she’s just used to brute forcing her way past opponents, and she’s never felt the need to change that.
 
Chrysalis cannot teleport herself, and she’s never used a shield to help her in a fight either, which are serious disadvantages against more skilled opponents like Celestia, Luna, Twilight, and Starlight, if they’re not getting taken down by a cheap shot due to luck.
 
Starlight has always been rather good at dodging. (Special note goes to that last one)
Dark Dash

@AC97
 
I would lean more toward this, since Chrysalis has only ever been successful in a head-to-head confrontation once, and it was because of the love she had sapped from Shining Armor. Her only other battles have been when the odds are tipped in her favor to an extreme degree (in one of the alternate timelines, and in the Season 6 Finale). Since her head-to-head battle against Celestia in the S2 Finale, she’s never fought any other character until she faced Starlight in the S9 Finale.
 
Couple with Chrysalis’ arrogance and lack of good judgement, it only makes sense that a more level-headed and experienced fighter, like Starlight, would be able to beat her through strategy if not through pure magical strength. I think that was Starlight’s intention for the most part, if we’re analyzing this to any degree, to anger Chrysalis so that she starts making mistakes and then take advantage of those mistakes when they present themselves. Especially since Chrysalis never seems to learn from her past mistakes anyway.
Vivace
Lunar Supporter - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Artist -

“ShimSham my GlimGlams”
@Dark Dash  
Starlight’s a smarter fighter. Most of what she did was rapid-fire teleportation to evade. She never actually directly blasted Chrysalis like she did Discord, whom I bet a few viewers wanted her to blast again after his in-character, but utterly boneheaded, scheme.
Hakirayleigh
Wahaha! - Derpi Supporter
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Preenhub - We all know what you were up to this evening~
Friendship, Art, and Magic (2020) - Took part in the 2020 Community Collab
Dream Come True! - Participated in the MLP 9th Anniversary Event
Economist -
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends
A Tale For The Ages - Celebrated MLP's 35th Anniversary and FiM's 8th Anniversary
Bronze Bit -
Sapphire -

ℜ𝔞𝔯𝔦𝔱𝔶 𝔟𝔢𝔰𝔱 𝔭𝔬𝔫𝔶
@Dark Dash  
I would want a longer Gim vs Chrysalis battle. But Chrysalis in her 2nd form she had more power than Glim. Starlight needed more strategy maybe.
Dark Dash

@Background Pony #365E
 
Fair enough. Still, she wasn’t having trouble with her and even taunted her twice, and could’ve won if she hadn’t let her guard down.
 
Really I don’t know if how that brief fight makes Starlight look overpowered that she can take on a more powerful version of the former Queen of the Changelings while only being a unicorn herself, or if it makes Chrysalis look like a terrible/predictable fighter, or both.
Dark Dash

When you think about it, Starlight is the only one who actually put up a serious fight against any one of the villains. Lord Tirek demolished the Pillars, and the Mane Six and the Princesses had trouble with Alicorn Cozy Glow (though they did beat her in the end), but Starlight actually could’ve probably taken down Chrysalis on her own based on how their fight went if she hadn’t assumed that she’d beaten Chrysalis so quickly.