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maybe they hide it, because they know you are a kleptomaniac?
The way I did it, I first talked to smiley in the backroom of the church, this will make him go to Blaubert's mansion to confront him. This is the most difficult part, as smiley will initiate combat while standing out in the open next to all the melee enemies, but if you can keep him alive he will join.
Then you can simply go to the prison basement, there's a guy called Luigi in a cell, you can simply kill him and his henchman right there and he will drop the machete.
Then find Smiley and side with him to get him as a recruit. Sadly, the Boss has to die.
There's no reason to keep the Boss alive but I feel bad siding with Smiley, as the Boss did not kidnap Smiley's "girlfriend": she chose to be with the boss, not Smiley.
What about luigi? boss wants to free him but luigi wants to kill him lol
Boss has you free Luigi so that he can make an example to people who double cross him.
But for OP, I free Luigi then have the confrontation at the mansion, then go save Smiley in Fleatown, back to the mansion and there you have three choices:
1:kill Sweety-Meaty Booboo
2: kill Smiley
3:talk Smiley down and he will go back to Arulco
Game #1 Did the Luigi quest first, sided with Blaubert, easy fight got the machete. Then did the Smiley quest, sided with Smiley, very hard fight, got the merc.
Game #2 Did the Luigi quest, sided with Luigi, medium fight but couldn't keep Luigi alive (He really fights like he doesn't want to make it) every named character died except Mollie. Then the Smiley quest didn't have choosing sides or a fight, he just joins up after Mollie blames him for hiring you to kill Blaubert (Which isn't how it happened but hey-ho)
I've heard of people having Smiley and Luigi show up at the same time, which is apparently one of the most difficult fights in the game if you want Smiley afterwards.
Also in the first game Smiley was a creep who wouldn't listen to anything Mollie said and didn't respect her choices about her own life to the point he was willing to get dozens of people killed for it and in the second game Mollie jumped to conclusions and wouldn't hear two words about what actually happened even though she literally saw Luigi do it. They're made for each other.
Had this happen in my 2nd run through. Rescued Luigi before ever visiting Rimville and did the smiley quest properly along the way since in my first playthrough the wall in the church was broken from the fight so it sequence broke his quest more or less. Though the dialogue accounted for it at the time somewhat iirc. So my first arrival to Rimville had Smiley Luigi and Boss all in the yard ready to throw hands.
1. Sided with Luigi. Could not keep him alive. Even with Booboo dead, and Joseph and Mollie alive at the end, there is no follow-up quest from either of them. Oh, Booboo can drop a 60% DR helmet. Was able to get Smiley to join at the end.
2. Sided with Booboo. Easiest choice. Got 10 rep with Fleatown and $3000. And of course, the Thing from dead Joseph. No loot from Luigi. Got Smiley at the end.
3. Sided with no one. Great choice for people who enjoy pain as both Booboo's and Luigi's teams will join forces against you.
In any of the scenarios above, as long as Mollie is alive at the end, Smiley joins your team.
I've played through the game three times and haven't recruited smiley once. He is a crap merc that isn't good at any one thing. Even his perk sucks. Plus he creeps me out. He is good for training militia.
Siding with the Boss gets you money, a mag, respect, and a boost to mine income. I'll take that.
If you get the Thing, give it to Mouse or to your melee build IMP.
The reason why you free Luigi, is to get him to fight Booboo for you. You can also then side with Booboo, setup safely in the high ground, then double-cross Booboo and kill both Booboo and Luigi. It was a jagged alliance.