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safe2280181 artist:tsitra3601424 applejack208495 king sombra17894 lord tirek6476 lyra heartstrings35392 nightmare moon21457 pinkie pie266686 pony of shadows733 princess luna121057 queen chrysalis44024 rainbow dash290969 rarity226078 twilight sparkle371496 alicorn336635 centaur4979 changeling70412 changeling queen25676 earth pony550658 pegasus542107 pony1710063 unicorn587026 g42122633 antagonist2630 appletini532 bench3928 blank eyes845 chess532 chess piece148 chessboard158 chessboard incorrectly oriented33 cloud46326 cloudy7043 evil smile7102 eyes closed149066 fangs44428 female1911035 figurine2493 forest16602 frown38858 glare9212 glowing eyes16476 grass17018 grin67309 gritted teeth20870 guard1740 knight1429 looking down16134 lying4697 male589497 mane six39186 mare813385 micro12727 mini applejack3 missing accessory10934 missing hat84 mountain8157 mountain range1145 mouth hold25306 no iris166 no pupils6759 nom3656 object323 open mouth257429 outdoors37248 ponified54416 pony figurine4 pony figurines12 prone38366 pushing1198 royal guard11488 sitting100317 size difference23963 sky25272 small pony205 smiling431086 smirk19165 spread wings105596 stallion215456 standing29470 tiny2388 tiny ponies2274 tree53885 twilight sparkle (alicorn)155214 unicorn royal guard348 wall of tags7973 wallpaper21265 wat22267 wing fluff2833 wing hands3237 wing hold837 wings252258

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Background Pony #C47F
Twilight confirmed for worst chess player. She always eats all the pieces!
Transparentist

Eldritch Exponentiality
@RainS604  
Same thing on the coloured old lineart of this I uploaded, it’s funny to see people looking for hidden things.
 
This version is so amazing tho really love th decision to move away from normal chess pieces  
There’s a lot less pieces laying around now and twi isnt a unicorn
Background Pony #766E
I was confused about the Lyra tag then after careful searching I spotted the 3 pixels in the background representing Best Pony
CommanderX

@chucklefarts  
Nope, just playfully roleplay with her friend. She gets an opportunity to feel like a mighty giant who have fate of her tiny friend in her massive hooves, so she may as well have a little fun with it. As long as she’s subtle about it, AJ won’t mind.
 
It’s not like she’s making it harder for AJ by secretly pressing against chess piece that AJ is pushing or forcing her rearange all chess pieces to their former position after her every victory. (Considering Aj’s pride, she could suggest a rule that the pony who lose the game needs to return all pieces to their staring position for another game, and AJ would accept it without a second though). Twilight is playing nice.
CommanderX

Twilight: Yes… yes… struggle for my amusement.
 
AJ stopped pushing and peeked from behind her chess piece: Did ya say someting Twi?
 
Twilight smiled sheepishly: J-just asking if you’re enjoying the game. It doesn’t matter if you’re lossing as long as you have fun.
 
AJ wiped sweat from her forehead: “Ah must say, chess are tough at mah size, but Ah like it better this way.” She returned to pushing her chess piece, struggling with each step.
 
Twilight raised forehoof up to her mouth and giggles. “The cure for poison joke won’t start working for a while. It seems we still have a few hours of fun.”
Background Pony #E760
I don’t think Fluttershy is in this like the tag suggests, unless I’m missing something.
Background Pony #7C03
Seeing PoS with Chrysy and her changeling and Sombra this really made me wonder about some conection beetween them, i’m not gonna mention about our night moony here, because we know some thing’s
PaintEdits

@chucklefarts  
Ehh I think you’re reading too much into this. The pieces after all are the exact same size and likely in the exact same number and power. Sure AJ’s going to have more trouble moving them, but she has just as good a chance at winning (in theory anyway, I wager Twilight would be a more adept chess player).
 
Size difference could just be for symbolism or just style. I’d guess the latter. What say you, @Tsitra360 ?
Background Pony #A3C7
It almost looks like twilight’s swallowing the pieces applejack loses. With applejack being the last to go at the end…