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Here's a thought. What about Yura from Sona's team being traded to Issei. She said that Issei was her kind of guy. Being part of Sona's team, she'd be good at performing tactics. Sona thinks highly of Issei as well for what he did for Rias so I could imagine her being willing to trade to help him out.
I could imagine Abe Kiyome becoming a pawn for Issei. The versatility of the pawn would probably be better for her style as a monster tamer. She's started to like Issei so I think there is a pretty decent chance.
Tiamat becoming his queen has decent chances. Ddraig says she hates him but I'm betting she's actually Tsundere and he's dense. If she turns out to have a humanoid form like Ophis instead of a mini dragon form like Tannin then I'd say it's a lock.
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