If sh*t hits the fan so bad that I have to dump everything and keep one, it would be my PSA 7 Neo Destiny 1st Ed Dark Houndoom that I pulled as a kid. I didn’t sell it for 20+ years, I don’t think I can do it for another 20 (also for $30, I think I’d work minimum for a few hours)
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I would just have four if it was the absolute last resort
shadowless charizard
shadowless blastoise
shadowless venusaur
shadowless red cheeks Pikachu
Give me my kanto starters and I’m good
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I cant do it. I could ditch a lot of the junk and bulk but i couldnt get my actual collections down in any meaningful way. I have gone through my graded cards several times and after approximately 100 graded cards i can toss out like 10. I enjoy 90% of my collection wholeheartedly.
Ive hoarded them for a reason, dont force me to rank their worth in my heart 
.
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I dunno man, sometimes I think to sell the most of my collection and just keep the most valuable stuff. So I would probably keep the entire ex Holon Phantom set and PLAY promos.
If we cut down to under 10 cards, so…
- Vaporeon PLAY promo
- Mew 080/PCG-P
- Dark Porygon2
- Porygon-Z 035/DPt-P
- Gyarados Gold Star
- Arceus Victory Medal 036/DPt-P
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The smallest I could still be content with would be the skyridge set and my japanese booster boxes and vintage blister packs.
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If I’m distilling down my collection to just a few cards, the penny pincher in me is really wanting to just keep the most valuable cards I own. But, to the person who just genuinely enjoys their cards and wants to keep the cards that mean the most, I’m really thinking I couldn’t part with my Harada signed cards. Not only are they awesome (to me), they also encapsulate my first ever in person Pokemon event, my first time meeting E4 members, first time meeting an actual Pokemon artist, on cards I hand selected with Pokemon that I enjoy. You really can’t beat that. I just love this trio:
They’re not the most valuable, best known artist, or most rare cards by any stretch. But they do showcase everything I love about Pokemon.
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If I absolutely had to, I’d keep the first Charizard I pulled, my Salamence ex (Power Keepers) I pulled, and my PSA 9 1st Ed. Shining Gyarados
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My collector’s corner
I could lose everything else except for what’s in the green square. The absolute core essentials of my TCG hobby, and if I had to, I’d say farewell to the rest.
- Arita Binders
- Lands Collection
- Special event dice / sentimental dice
As long as I have these pieces, I would still feel satisfied with my collection because of all the work and love that went into those parts.
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It’s funny because those are the exact four cards I would keep also. But also because they are all four cards I pulled from packs as a kid and kept in my collection. 
After that I’d just want to keep my original childhood card binder.
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Kanto is best
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“Smallest” I would try and go for a single binder page. And this is what I’d have:
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I see you also have fantastic taste 
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I spent way too much time thinking about this thread for the last 2 weeks. But it was a good exercise. Don’t own a Unikarp, signed Masago Kabutops, or 2014 worlds promo but hopefully soon!
Edit: already changed my answer 10 minutes after posting
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Here let me give my hypothetical, i saw this thread when it dropped and havent posted, so here is mine. Smallest i could make my collection. Competitively Viable cards from Base-Legacy, and their theme decks.
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I could sell off everything but my PSA 1st Edition Base collection, and be totally fine without any remorse or lost nostalgia.
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yeah it’s not easy lol
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I’m trying to think what a good number of cards is. Like do I want a theme, a set or just a random assortment?
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yeah it’s tough to figure out what would leave you satisfied in the end.
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