United We Split Up

How could a group with this much super-powered muscle:

...still wind up in the slammer?

The "Sinister Six"--from the classic Amazing Spider-Man Annual #1. A team of villains which probably broke the record for a team showing the least amount of teamwork--in their case, NONE. Next time, take a note from Aesop--he knew what he was talking about.

Or you could listen to the Vulture, trying to get a word in edgewise:

And to reiterate:

But chomping at the bit, these villains just wanted to get going and do something--in this case, eighty-six Spider-Man. So they eagerly and impatiently embrace a questionable plan from Dr. Octopus, their de facto organizer/leader. Octopus has them draw cards with numbers and locations on them (including, presumably, their names), which dictate the order in which each of them will engage Spider-Man in battle. His reasoning for dividing their power?

So the plan is two-pronged. Each battle location will play to the strength of the villain who shows up there--and Spider-Man will be more tired and weakened after having to fight one villain after another.

Yet there's a flaw in the plan already. Each of these villains has already failed when the location advantage was theirs. The Vulture fought in the sky; with Electro, he had the city's power lines at his disposal; Mysterio always had an elaborate set-up; and so on. So there's no clear distinction in this regard between this series of battles and those that came before.

And Spider-Man being weakened isn't really a bad strategy so much as an uncertain one. It all would depend on how well he did against each villain. If, in Kraven's case, he came out relatively unscathed, the battle has had no real effect on him. Electro's bolts would have to make contact with him in order to harm him, bolts which Spider-Man has dodged before. Sandman or the Vulture could do some major harm, if they put their respective minds to it--but in this case, they were easily outsmarted. So when Doc Ock, Spider-Man's last opponent, finally makes his play, he's facing an enemy not only generally unharmed, but motivated to free the two people dearest to him from being Ock's captives.

Also, wouldn't Spider-Man become tired and weakened fending off attacks from six super-powered villains at once, as well as he might in sequence? Maybe even more so? Particularly if this "team" had gotten its act together and launched a carefully planned attack.  And just look who ends up getting to twist that particular knife:

Better luck next time, gentlemen. Just keep in mind: joining a team only to draw cards and split up is a terrible way to utilize strength of numbers.