We know that Doffy met his four executives (Diamante, Trebol, Pica, and Vergo) as a kid and how. But we never seen how he met the rest of the crew (except Law). Do you have any headcanons how he met the rest (like Senor Pink, Gladius, Giolla, Machvise, Dellinger, Baby 5, Buffalo, Lao G, Sugar, and Monet) or the backgrounds of them before they met Doflamingo (most of them are mysterious except for Law, Corazon and Baby 5)?
Señor Pink - maybe while robbing a bank, maybe Señor was an accountant Doffy met and he helped Doffy rob a bank, or myb Pica found Señor Pink (I say Pica cus their powers are similar so he might have bumped into him while going through the ground which would be rather funny xD)
Giolla - art thief/made fake paintings to sell on black market or they met at a designer clothes gala, Giolla got fired and then killed her employer, Doffy loved it. That, or she killed her rich husband who she hated and took all his money whichever way you want to look at it, BADASS WOMAN
Machvise - Doffy (14)met him at a food fair where Machvise won a hamburger eating contest. Later, Machvise got chased by marines cus he robbed one of the Celestial Dragons' ships as a shipwright bcs the shipwright company didn't give him enough money and removed his name from the blueprints bcs he wasn't "proper" enough to be introduced to the CDs as a shipwright. Doffy saved him and challenged him to a food eating contest, if Doffy wins the eating contest, Machvise joins the crew. Doffy won.
Gladius - Orphaned by the war, he grew up in a war-torn country surrounded by bombs going off all the time and had his hearing severely injured that he got extreme hearing sensitivity. Any loud noise gives him headaches and makes him scream in agony - therefore the earmuffs on his ears. Starving one day, he ate the Pop-Pop Fruit and went into a one against all at the risk of his own life. He was found by Doffy. This happened when Gladius was 7 years old and Doffy 17.
Buffalo - worked at a welding factory (child labour with kidnapped children), stole ice-cream from a store for himself and the other kids at the factory to eat something in the heat. Doffy was curious cus he was in the same shop and saw Buffalo steal the ice-cream. Doffy ended up busting the factory with his crew bcs Trebol found out the owner was keeping money from the DQ Family and faking how much weapons he was selling. Doffy saw Buffalo in the skirmish of marines (who the factory owner hired in an attempt to protect himself from Doffy) vs pirates and saved Buffalo. The reality of the marines was that they were just pretending to help the owner cus they were trying to get two birds with one stone - the pirates and the owner. They were there to arrest the owner of the factory, as Corazón tipped off the marines about the entire child labour. The marines took all the kids home, but Buffalo had nowhere to go, so Doffy just put his hand on Buffalo's shoulder and said "This kid's with me." And then took Buffalo for pancakes, cakes and ice-cream. Buffalo cried for two days straight.
Lao G - Diamante met him and got his ass kicked in hand-to-hand, so he hired him 🤣 maybe Lao G owned a dojo but it was losing business bcs of how strict of a teacher Lao G was, Doffy was 13 when he met him and got a lot of his training from Lao G
Baby 5 - there is this great fic "To Be Needed" and in short I consider that one my headcanon. Doffy visits Kuja island, probably gets lost in the same mountain range where Baby 5 got abandoned, finds Baby 5 starving there and just sees red. Burns her village, kills everyone in it, and takes Baby 5 with him.
Dellinger - at a slave auction (or while DQ Pirates search through an abandoned laboratory) Giolla notices him first. A mess ensues. The entire thing gets blown up and set ablaze by Doffy, Doffy is carrying Dellinger out of the fire and is interested in the hybrid fishman and decides to name him Dellinger. Dellinger was made in a lab, his mother was a test subject and died giving birth to him. The scientists fertilized her with the... Well, sperm of a male Fighting Fish. And that is how Dellinger came to be. He looks 100% like his mom, blond curly hair and all other features. The fishmen don't want Dellinger cus of his human blood, the humans don't want him cus of his fishman blood. But the DQ Family wants him. He's theirs now. Note: If Dellinger's mom got the chance to name him, she'd call him Hikaru, which means light, bcs of his yellow hair like the sun 🥹 (aaaand now I made myself cry)
Monet & Sugar - will be a little arc in M&P so spoilers for the story ahead...
They lived in a cold kingdom in North Blue (much like Drum Island) and were starving with most of the commoners. Monet got caught stealing food and nearly got enslaved by the king but got saved by Sugar - who murdered the guards with a dagger by cutting their throats - and while on the run, they meet the DQ Pirates. Myb they accidentally eat their fruits from hunger, who knows. TBD, cus that is some luck to get those exact fruits.