Doflamingo's plan with the tournament seemed to be to lure in a bunch of potential threats and have them all wipe themselves out. Of course, the last man standing would be an even larger threat - having eaten the mera mera no mi - but that last man is meant to be Diamante. Nevertheless, I think it is clear that Diamante was outmatched in that last round, so I am wondering if (1) Doffy was okay with someone having the mera mera no mi, (2) Doffy had a contingency plan to eliminate the last man standing, or (3) Doffy just seriously overestimated Diamante and/or underestimated everybody else.
Someone else having the mera mera no mi seems to increase potential threat to Doffy, not decrease it, so I don't believe (1). Since Doffy was expecting Law, I doubt he was ready to deal with the winner himself, and we have no hint of a contingency plan so no reason to suppose one - I don't believe (2). With his love of his family, and how arrogant he (AND his family) are in general, I am leaning towards (3).
Flash forward to now. His family members are being beaten by people who, best said by someone earlier in this thread, were "FODDERIZED" by Luffy. And the family is - by and large - cocky while fighting, too. He didn't expect anyone to foil his plan, and he and his family are all confident in their abilities even when the plan became foiled.
I like seeing contrasts between new world and paradise (so far, anyway). Clearly, Doffy and Crocodile are comparable in a lot of ways. They also contrast. Their similarities and differences highlight developments in the one piece world. The difference here is why their plans failed. Crocodile and Doflamingo are both arrogant and treacherous, overthrowing Kingdoms in an attempt to further their goals.
Crocodile essentially succeeded, but never really did take over Alabasta officially (as far as I know). He underestimates Luffy, not even bothering to "finish the job." Luffy of course comes back, again and again, and wrecks Crocodile.
Doffy officially takes Dresserosa, and rules it for years. Though arrogant, he is not reckless, recognizing potential threats and devising a tournament to have them wipe each other out and be subsequently turned into toys. When it comes to fights, he finishes the job - with a pistol shot right between the eyes. He does not take chances, and you can bet there are no second chances when you fight Doffy. Yet, he does look down on others anyway, and he overestimates the abilities of his crew (while Crocodile somewhat underestimates his crew, treating them - by and large - like simple pawns, most of whom he sees as incompetent). This is a kind of recklessness; Doflamingo literally devises plans to handle his problems, but if the plan fails he is over-confident that it won't be a problem to take care of. (This might be an inconsistency within his character).
What am I getting at?
Well, back pre-time skip, it was somewhat alright to overestimate oneself, but not to underestimate one's enemies. Luffy was reckless, as he was going to surpass everyone. Crocodile underestimated the strawhats and it cost him. Back in PH, Zoro tells Luffy not to get reckless, and to take the new world seriously. I viewed this as "Don't underestimate the enemy!" but I think I was wrong. We are now seeing Doffy fail, not necessarily because he underestimates his enemies - heck, he viewed them as worthy enough of eliminating via tournament - but because he overestimates himself and his crew. I think this is an important reminder that overestimating yourself can lead to failure just as easily as underestimating others, and what Zoro said could foreshadow that. Especially since the Strawhats are coming off of a 2 year training break (some of whom trained with the very best), this serves as a reminder to us, the readers, not to overestimate the strawhats.
The New World is no paradise - and the Strawhats are still not an especially seasoned crew; there are pirates here who have careers that span generations, and they are not as quick to underestimate their enemies as Crocodile.
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