jmacavali
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All the solutions posted so far ignore that the OP asked how he could plug just his subwoofer into the headphone jack and have it play along with the laptop's internal speakers. He didn't want to buy a new set of speakers (which would allow him to use the new speakers with THEIR subwoofer).
Upon re-reading the thread the OP does not make mention of a "car" sub...I guess I made that part up in my head...sorry...
I'm going to go with strollin and say no, since the headphone port should disable the internal speakers.