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Is this yet another thread which you use to criticise some partner who irritated you? The answer is obviously 1S. Even in the bygone days when it was normal to double with a 5M431 hand this would probably have been a 1S call for the majority. The reason is that while double is more likely to get us to a playable spot in one go, this hand will happily double 2C (or bid 2D if preferred I guess) from the opps next time round. Thus we get the best of both worlds - we show our 5 spades and also the take-out shape. If we double first instead then we cannot compete with 2S over 2C since that shows a better hand, not to mention that it is less flexible.
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1. Not only do I have a 5 card suit to overcall, but it's the boss suit, and the suit that I want partner to lead for defensive tricks. This is not close. If it goes P-P-2C back to me, then I will X.
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1 now and double if it comes back to me at 2.

 

My style is usually to overcall with this sort of shape even if 5=4 or 4=5 in the majors and judge whether to double the second time. The exception is when I don't think that I am good enough to double the second time and my five-card suit is poor.

 

Obviously at times doubling first can work out better e.g. if the auction is too high to make a double when it comes back.

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