This has always been one of my favorite controversial topics, right after the OS wars.
I think it was summed up best in a magazine article I read years ago that was focusing on the CEO of MonsterCable... They attributed his massive wealth and success to "creating a cure for a disease that didn't exist". And of course, there's all the articles written by electrical engineers talking about how ridiculous it is to spend $100 on a cable that you plug into a $.06 connector on the back of the stereo.
I've always gone by the opinion that as long as you're not picking up excessive noise, running a recording studio, using too small of a gauge, using poor connectors, or anything weird like that - that you'll never know the difference between the $100 MonsterCable and the $7 RCA cable. Same goes 10-fold for these fancy ridiculous HDMI cables. You can get those online for $5 - and they work the same (beauty of digital - it works or it doesn't; there's not too much in-between - at least for short runs).
I think to most people, it's the placebo effect... and if that works, then by all means, spend the cash - and yes, connectors can matter (different metals, etc) - but hell, if you think that's the issue, there's those contact chemicals which you could lightly apply that would eliminate that issue (but you'd have to be pushing the limits of the connector for that to come up).
Given the prices of subwoofers though, I'd spend $20-$25 on a mediocre cable that has sufficient gauge and is one-piece back to the subwoofer... and if that doesn't solve it, step up to a better subwoofer. Also, in that particular case, you're extending the non-amplified signal a decent distance (assuming powered subwoofer), so any hint of noise would get amplified - therefor you'd want to minimize distance to noise sources, and in that case, maybe seek out something with a little bit of shielding.