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Reading through this thread I found it consistent with past street racing around my area.

Yes, some folks whipped up on a 440 with their 383. Others whipped up on a 383 with their 340. Yep! In many instances, the 440 cleans house too.

This would seem to indicate that a well matched engine build, a balanced drive train, a fresh tune-up, and someone who knows how to drive their car can easily break the gap to any advantage 40-to-60 cubic inches can have.

But regardless of actual performance, the bragging rights the 440 yields always wins out simply because it’s the biggest passenger car production engine Chrysler built.

Bigger is always better, right!?!?

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Bigger motor + less cash outlay to put in more power = winning strategy!! Nice formula!! But...
sometimes it's not, depends on how well ANY given combo is put together (parts matching and TUNING)!!