The cigar boom was created by Marvin Shanken and his magazine Cigar Aficionado. Before the magazine came out, you could buy all of your favorites any time and you didn't need to worry about stocking up because something might not be available. Once the boom was in full affect, most legitimate non Cubans became hard to find, even JR had huge back orders. I used to buy Fuente 858's for 17 bucks a box in the mid 80's. Now they retail for 87.50.
The boom created tons of shit cigars and all of those who mfg. them eventually went out of business. What we have left is the greatest amount of quality cigars that has ever been in the cigar industry. The amount of competition today is making cigar mfgs produce better and more variety of cigars than there has ever been. Back before the boom there were not nearly as many different brands or blends as there are now. There are so many more choices for us cigar smokers, but the prices are indeed a lot higher.
The quality of some of these cigars is unprecedented; the only thing about the pre boom cigars that was better was the quality of the Cameroon wrapped cigars. Back in the mid 80's to early 90's the Cameroon wrapped Upmanns, Fuentes, Partagas, and Royal Jamaican Park Lanes were the toothiest Cameroon you have ever seen. Today that Cameroon wrapper isn't quite as good, other than that the cigars being made are superior to what was being produced before the boom. The amount of technology being used by a younger generation of cigar maker is way above what the old school guys used.
As far as Cuban cigars are concerned in 1999 Cuba decided they wanted to make 200 million cigars. They had never even made 100 million before that so they opened a ton of new factories and their quality went to shit. The tobacco itself wasn't that big a problem because the 1998 crop was one of the best in Cuba’s history. It was the blending and construction that took the huge hit. Before 1999 there were serious shortages to the most popular sizes i.e. Monte 2's Partagas Lusi's HDM DC and Serie D 4's to name a few. However there were still tons of less popular cigars i.e. Partagas SD1's. Upmann Lonsdale’s, Sancho Panza Molino’s that were available and smoked great. It took Cuba until 2001 to start getting their shit together and for the most part their quality in construction has greatly improved. They of course never got close to the 200 million number and have abandoned that ridiculous idea.
This is just a basic description of what went on there were of course a lot more things happening at the time.
One interesting note was when the new mfgs during the boom lured hundreds of Fuente rollers away with big promises of money. Those rollers were soon out of jobs and looking to go back to Fuente. He didn't take one back. Instead he turned factory no. 4 which is still run to this day by Juan Sosa into a sort of college for rollers. He took young people with no experience and trained them all to roll cigars in the old Cuban style of En Tubar. This method is basically taking each individual leaf and rolling it into a tube and then adding each tube into the bundle and then wrapping the binder on to that. He created a completely new work force that had no history of bad habits. This is one of the main reasons that a Fuente cigar is constructed so well.
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