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My assessment of the Tobi Roppo fights:

Drake: Defects but pairs up with Chopper.

Ulti & Page One: Two-on-two like Mr. 4 & Ms. Merry Christmas but Big Mom does 99.99% of the work. (Remember, Ulti also attacked Usopp and he assisted Nami in taking Ulti down.)

Who's-Who: Most Tobi Roppo are on Diamante and Trebol's level whereras he's on Vergo's, which makes him too strong for the mid trio. Ideally, Jimbei should fight Jack (third strongest right after their captains), but the Dukes want Jack's blood, so Jimbei makes due with the Beasts Pirates' "Blueno" instead.

Sasaki: Close to Who's-Who in strength but weak enough to lose to the strongest(?) mid trio, Franky.

Black Maria: Really Robin's fight.

Brook and Chopper get the short end of the stick (again, Chopper was paired with Drake, and Brook did neg diff a Number and a bunch of Gifters at the same time).

With the Disaster fights coming up, Jack should go down first. I imagine Perospero is there to waste Neko's time to add tension between Inu and Jack. I prefer if Chopper takes down Perospero (and I will squeal with joy if he does), but it is what it is.
 
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