>>62875409
>Serious(ish) answer
Stage a series of false flag attacks along the Cardassian side of the border. Have the Obsidian Order use whatever skulfuckey they need to to make the attacks look as horrific as possible while doing as little actual damage as is necessary to sell the attacks as genuine, we'll probably need at least a few million dead and a number of the less useful border worlds rendered uninhabitable for decades. Make sure that news of the 'not so obvious' links to the Federation that the Cardassian investigation turns up - including testimony of several Federation citizens taken into custody following their conviction for terrorist activity. Use the political pressure to claim that the Federation are covertly attacking Cardassia, and agree to a diplomatic resolution where you can use the stink all of this has caused to force significant territorial concessions out of the Feddies (at least major enough to warrant the cost). If at all possible make sure that the Enterprise is off doing something Borg related on the other side of the quadrant while all of this is happening.

>Much more fun answer
Have Pa Wraith empowered Dukat one-man-army his way through the entire Federation fleet to Earth, conquer the federation personally, and order the construction of a truly kick-ass statue of himself in the middle of San-Francisco, make it at least five times the height of the Statue of Liberty.

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You are in command of Cardassian Union during Border Wars. How do you win?