Throughout the game I was wondering why Gilbert was the final love interest, especially since Dante's route felt like it explains so much of the church storyline and Gilbert doesn't seem involved in that at all.
That said, starting his route was a lot of fun because the game knows the player has a certain baseline of information to work with, including the back stories of all the love interests aside from Gilbert, so even if Liliana is bewildered about a three way battle erupting in the church when Yang comes to kidnap her, it's laughingly business as usual to the player. The only thing that was a little weird is that after fighting breaks out between the Lao-Shu and Falzone, Orlok is the one to rescue Liliana from Yang and send her running out into the night clad in nothing but her nightgown while he tries to hold everyone else back.
So while everybody who is aware that she's a valuable person is fighting, who does she bump into but Gilbert Redford, who is out for a late night walk. And I was (probably unintentionally) amused that after offering her shelter and security, Gilbert declared that the safest place in Burlone is next to him. Considering that he is the one love interest who has been killed by every other love interest on at least one other route through the game, I probably would have felt safer with anyone else (barring Yang).
Gilbert is a bit of a showboating braggart, though part of his bragging encompasses caring for the city and being a generous steward of his district, so the people of Creta generally think favorably of him. And since he's the love interest this time around, he gets to live up to his boasting. With him coming last in the story sequence though, I can't help finding Gilbert a bit of a hypocrite. Though Dante also suffers from dissonance between what he says and what he does (particularly when he's not Liliana's love interest), Gilbert feels worse about it because he is so gleefully out there like a kid in a candy shop. Dante doesn't engage in chest thumping over his morals, but Gilbert loves to talk about the lines he won't cross, which by this point the player has already seen him crossing six ways to Sunday.
I think, given his personality, he would have been more fun as an earlier route than the last one, especially since the main plot of his route has nothing to do with Liliana's status as the Key Maiden and instead jumps into this weird money counterfeiting plot, which I think may have been where the writer originally started spitballing the premise of the game (since it takes advantage of Burlone being "the back door to Europe" which is mentioned in the prologue but discussed on no other route) before it started wandering into church conspiracies.
Though Liliana being the Key Maiden does come up, fairly early and so abruptly that Dante is left glaring at Orlok like "Did you really want to tell every mob boss in the city the whole history of the Falzone and the Key Maiden?" it feels like it's just there to address why there was a three way battle to get her at the start of the route. After that point it's mentioned a couple more times, but it's clearly not the priority.
Confusingly, the Lao-Shu and Orlok are not allied in Gilbert's route, resulting in conversations that show they clearly aren't on the same page the player expects them to be, but not why that's different from previous routes, until about halfway through when the game decides to drop a Meanwhile scene between Rosberg and Emilio to show that for some reason or other Rosberg changed his mind, possibly out of concern he was going to get kicked out of the church. That would have been nice to have before the three way mob boss meeting when Orlok and Yang meet for the first time post-church battle, instead of a couple chapters after.
Given that the Key Maiden storyline that has been the inciting incident of every other route thus far is tossed to the wayside, why is Gilbert the last route?
It's because Gilbert has the closest thing to a golden route, the storyline where generally speaking everyone's individual stories get tied up with a neat bow and the player can see the cast at their best one last time. Not every game has them, and Gilbert's does not come without sacrifice (alas, poor Nicola), but this is the route that sees all three mafia families set aside their differences and work together.
Shortly after Lili moves into Gilbert's place, he ends up getting arrested on charges of counterfeiting American dollar bills, but is able to get out on bail with three months until his court date. Because the mafia families are the prime suspects of counterfeiting, he's not surprised the real culprit would pin it on one of them, with the Visconti being the likeliest target due to their American connections. However, the Falzone, Visconti, and Lao-Shu are also businesses in a sense, and the three bosses agree that none of them would counterfeit in their own city because no one would ever cut a deal with them again if they could potentially be paid in fakes.
And hilariously, Orlok shoehorns himself into the group under the grounds that the Church wants this counterfeiting stopped since it would be a global problem given the dollar's value internationally. I like Orlok, but it was pretty weird having the church assassin show up in the name of economic stability. Really, the only reason to have him around as much as he is, is because Gilbert's trying to have a golden route.
Trying, because eventually Nicola gets killed as a warning to the Falzone to break off their alliance with the Visconti. I really like how Dante handled receiving Nicola's bloody jacket, and his decision not to step away even if it meant signing Nicola's death warrant if he wasn't dead already, but it kind of spoiled the golden route vibe the story otherwise had going for it.
At first the cooperation felt like just a bit of lip service as the three families conduct their own independent investigations and choosing to just share information with each other, but by the penultimate chapter, every family, every boss, and yes, Orlok, gets to have a part in the operation to take down the counterfeiting factory and the boss at its head. Even Rosberg plays a part by testifying to Gilbert's character in court. (Though to avoid lying on the stand, all Rosberg did was confirm that Gilbert was a devout follower of the Church and has made many large donations.)
It really made Gilbert's route feel like a farewell blast, and the story manages to do all this while still giving Lili plenty of time to fall in love with Gilbert. Since she's with him almost the entire time, even the meetings with other bosses, this puts Lili in an uncommon position for her. She's party to the majority of important conversations and often knows as much as anyone else in the room, allowing her to draw her own conclusions and participate in the discussion.
When the mafia bosses lose the casino as their meeting spot because Gilbert realizes the casino staff is on the counterfeiting, Lili is the one who suggests and arranges for everyone to meet at the church at night after the parishioners have left. She is really on the ball in this route, and I'm not at all surprised that Gilbert falls for her.
Aside from Nicola's death, the other thing that makes Gilbert's best ending feel less than golden is the resolution with the culprit. The casino dirretore is the mastermind, and though we know from Orlok's bad ending that he hates the mafia, and that he engineers Lee's ascension to villain in Yang's route, we don't know much else about him. Gilbert isn't even his real target as he mentions he couldn't use Dante as the fall guy because he considers the Falzone the main course. The Visconti are just the appetizer.
Marco and Roberto, our police detectives, are unable to get a concrete motive out of the dirretore after his arrest other than him rambling about hating the town (a direct contrast to Dante and Gilbert who repeatedly express their desire to protect the city), hating the mafia, and wanting everything to burn. He wasn't the only one involved, being backed by the Liu Huang Hui (Yang's parent syndicate), but he was the local commander and face of the operation, with the suggestion of Italian government officials also being involved as part of Mussolini's crackdown on the mafia.
In Gilbert's best ending, all three mafia families settle into a bit of live and let live and stop fighting each other so much, which is probably the most we could ask for. I wouldn't say they're making friendship bracelets for each other, but I think knowing that 1) the Church will keep the government off their backs if the city is safe and that 2) the three families can accomplish a lot if they work together, has them wanting to keep the other guys around as potential allies should the need arise.
But because of that leftover plot thread with the dirretore, there has to be one more route to finish off the game, and that's the Finale.
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