I'm still nursing a pet theory that Drest is in fact the Dalmascan prince, Rasler. In FFXII's story it was Rasler who was killed and his wife Ashe that "died" under mysterious circumstances, but in XIV they were siblings and she was confirmed dead by her bodyguards after having been shot (similar to the original Rasler), while this version of Rasler is simply thought to have died during the chaos of the battle for Nalbina Fortress. Of course in XII, Ashe actually survived.
There's also some unusual details with Drest. First off he says that he had two children back in his homeland, a son and a daughter, who were very young when he left Dalmasca and think he's dead. Notably Lente's Tears is supposedly led by a princess Ashe, but this can't be the actual Ashelia both because she explicitly died, and because she'd be in her late forties rather than being a relatively young firebrand as the resistance leader is described.
Next, there's how Drest is described by his ex-squadmates. They call him "Dashing Drest", and say that he was always craven, and call him a "Desert Conie", or desert rabbit, that they've flushed out of hiding. Drest says he never tried to run while in service to Garlemald, and that he earned the nicknames back in Dalmasca. Of course Dalmasca is known for having ties to the Viera (rabbits) and some were even known to be part of the royal entourage, and it makes sense to mock an ex-prince considered a coward as "Dashing". After their deaths, Drest also says that there's no-one left that knows he's alive - Obviously not true, but it
would be correct if they were the only ones who knew of his true identity.
Later, during the Ivalice quests, Drest comes up again a few times. Particularly, you're suddenly sent by the Wandering Dramaturge on a wild fetchquest back to Eorzea looking for a bottle of Dalmascan wine that hasn't been seen for decades. This quest, which is mandatory to the story and has you meet Drest again and recover an empty bottle from him, happens
right after the quest where you're first told about Rasler and learn about Ashelia's death. During this, he again brings up the constant buzzing of the midges that haunt him at all times, and equates it with the screams of his comrades in Dalmasca as they burned and he could do nothing to stop it. Of course the screaming, burning, and "buzzing of midges" is somewhat reminiscent of the Garlean airships bombarding Nalbina Fortress and slaughtering over 70,000 Dalmascan soldiers in the decisive battle that effectively ended the war for the nation.
Then, after the series is done, there are more sidequests dealing with the wine. A store of Dalmascan wine straight from the royal family's cellars was spirited away to Orbonne before the capitol was taken, and is discovered by the resistance following WoL's venture to the area. As way of making up for having previously scammed some people using Drest's old bottle, WoL then delivers a few bottles of the legitimate wine to various people, one of which being Drest himself. When he opens the wine, Drest says this,
So to Drest, this wine
which comes directly from the Dalmascan royal household, is the "scents of home".
Lastly, there's the matter of Drest's name. If you look into it, you'll find that it's actually a now-obsolete form of the word "dressed". This would be a pretty appropriate name for someone that's been stripped of their identity and indoctrinated into the Garlean military regime so hard that he reflexively repeats the mantra "Idem in me...by the majesty of Garlemald...never to desert...idem in me!", when he's confronted with having ran away. It also adds another layer or mockery to the nickname "Dashing Drest", since it further ridicules the man he was.
Maybe I'm just crazy, but this is all just
a little too suspicious for me.
