This is the start of a new series, about how this antagonist could've succeeded.
The First Episode is about everyone's favorite bird with glasses: DONQUIXOTE DOFLAMINGO.
How it Failed.
Doffy's plan was to take over Dressrosa, and that succeeded, but then Straw Hat and Friends came along and destroyed all that. Most of his reign is thanks to Sugars Hobi Hobi no Mi, so after GOD Usopp fainted her, everything went wrong. So we need to make that plan better. Another thing that went wrong is the Corrida Colosseum stuff, if he didn't organize that, None of the allies of the Straw Hats would've come, except for the Revolutionary Peeps. Big, Big Mistake that is Doffy.
Also, If he didn't make the decision to fake resign from the Warlords, Fujitora wouldn't come to Dressrosa to investigate, and no Marine would know, about the shit that happened. Well, they would eventually find out, but later.
How to fix these problems.
The first problem would be fixed by making someone who doesn't hate Sugar her bodyguard, Like I don't know, HER SISTER. Not only would it become harder to faint Sugar, it would also keep Monet alive. That's a Win-Win for everyone involved. For the Spy in Punk Hazard, That can be Giolla, because no one cares about Giolla.
Problem 2 would be resolved by just not holding that tournament and then just make Luffy fight the Diamante Army to slow him down, easy peasy.
The final problem is a little harder than the previous one. because he still needs Caesar Clown, to fix that, he can say that he holds Law's crewmembers hostage to lure him in.
So that finishes the First Episode of How This Person Could've Won or HTPCW in short. Next Episode is going to be about: Everyones Favorite Sandy Reptile CROCOBOY