Being the Holy Grail is Suffering... [Worm/FSN Quest]

There's like five canon Avengers that could be summoned. Maybe four? No need to limit ourselves.
This is me assuming there won't be random Summons from outside the standard seven unless required like a Ruler is (which given that one needed to be forced anyway and given that Avenger Jeanne got shoved into the Ruler Jeanne with Grail Mud Consequences when they're separate Classes I'm pretty sure this is the case). Although I'm all for Summoning all the Avengers just for Shiggles!
 
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[X] Focus on Rachel

Alec might be fun but I feel Rachel will make for a more interesting story. Plus Alec doesn't want to get his father attention and this is going to cause a lot of attention to come his way.
 
[X] Focus on Alec

as long as Brian does not become a Master, i'm cool (he is suspectible to 'i give you a 100M dollars/we help you with your sister+lodgings+formalities and you relinquish your Servant to me' - Coil/Protectorate respectively)

if we get Alec and Rachel to voice their wishes, there is a possibility they have an 'i would like that too' moment and thus cooperate
 
Dantes, Angra, Lobo, Gorgon, Black Grail, Jalter, Kingu, Boudica, Amakusa Shirou, Heracles.

I count ten.
There's a list on one of the Wikis:
Avenger
Whether or not it's complete is up to you but in total it seems to be thirteen (not counting variations of the Angry Mango). I love that number so lets go with that.
 
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Nah. Shakespeare is more likely to treat Alec like a character in one of his plays. And that's exactly the kind of lack of control that Alec wants to get away from.
Honestly, I was thinking of giving Alec Medea. Both can bond over asshole controllers.
Now this on the other hand is brilliant.
Medea herself was basically Mastered into loving Jason before she even met him, and even when she did break away from him she still had no control over her life due to the label she got from doing atrocities on his behalf.
A Medea/Alec dynamic would be amazing and colossally fucked up.
Edit:
Another thought to just add more chaos to this already clusterfuck of a war. Medea has Rule Breaker and can steal other Servants. Double Master Team would be gold.
 
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as long as Medea is overseen by Ruler, she wouldnt try to cheat as blatantly as she did in Fuyuki, i guess??? and BB being an AI means Medea cant just Rulebreaker her for Command Spells

still, we can choose between Lily and the older one.
 
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