re: Had the South won would New Orleans be the largest/most populated city in the US?

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As a New Orleanian an that has lived in Atlanta (3.5 yrs) and Houston (6 mos); both cities would be larger than NOLA even if the south had won.

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Why? Because you happened to live there in recent years when they were nice?

We're talking about cities developing from a starting point 150 years ago, so I'm not sure how relevant recent personal experiences are. People think of the current state of New Orleans corruption, but New York was worse than New Orleans about that in the 19th century. New York was also really bad about organized crime from the 1940s through the 1970s.

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The north would have stopped sending goods downriver if the south had won and we would have been a backwater.

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Are you kidding!? Hell, KY & MO probably would have started a 2nd Civil War had Congress tried to stop them from sending goods down river, and the big business interests in Chicago and New York (who were the main drivers behind the Northern political movement for negotiated peace in the first place) would have never allowed it anyway.

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Charleston, Miami and Houston might have ended up as the biggest ports.

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No. There is no reason at all why Miami would be any bigger than it is today, and Charleston was in no position to compete with New Orleans, except as a potential auxiliary. It might have played the role of Boston to NO's New York.

Houston was of course geographically destined to become a big energy port city, but that was way off into the future back in 1860, and Houston would still have to play catch-up to the leading financial centers for the cotton, commodities, and energy markets. Had the South won, those commodity futures markets for the South would have undoubtedly been in New Orleans, rather than in Chicago.

Houston would still have emerged as a leading port city for commodity trading in the mid-20th century, but the capital of the energy markets would have been solidly entrenched in New Orleans by then. It's very difficult to dislodge a financial center once it's been established, due to the economics of agglomeration.

Potentially, New Orleans could have been more like London or Singapore or Hong Kong in that respect.

Going back to the 1860 census, and taking New York & Brooklyn as a single city, then New Orleans was 5th in population at 169k, and Chicago was 8th at 112k. Then Charleston was 21st at 41k, and Atlanta was 98th at 10k. Houston was not even in the top 100, having less than 5,000 citizens, and Miami in the pre-AC days was even smaller, having a population less than 100 people until very late in the 19th century.