High end luxury cars - Lexus, big Toyota SUVs - all stolen police say in what's described as "operation made to order."
Police say the men used information obtained by car dealership employees to make counterfeit keys.
"The ring was doing swift business at blue book value of nearly 10-million dollars," NYPD Commissioner Raymond Kelly said.
Kelly says the 21-member ring was reselling Lexus and Toyota vehicles in the U.S. and overseas.
New York Attorney General Eric Schneiderman says 16 of the people indicted face felony enterprise corruption charges.
William Cruz, the alleged operation boss, was able to run the operation for a time while in custody on Rykers Island on an unrelated charge.
"This was a multi level sophisticated operation. Even with the boss in jail they were able to carry on," Schneiderman said.
To retain a car's high value, investigators say, a so-called "steal crew" would go out and target the wanted vehicles, taking down their vehicle identification number.
Police then accuse two brothers, Joey and Eddie Aviles (who they say worked at Plaza Toyota in Brooklyn), with searching data bases to find key codes for those cars .
The owner of big daddy hardware, Vincent Abreu, and another man would then use the key codes to manufacturer counterfeit keys for the crew members to use going back out and grabbing the car.
"No matter how sophisticated your scheme, no matter how many insiders you think you have or how clever you are, you will be apprehended," Schneiderman said.
Investigators say the entire process for one stolen car would take about two days at most, and would generate a handsome profit.
"When all was said and done, cars that retail for 30-thousand dollars were being sold for as little as three to five thousand dollars," Kelly said.
According to authorities, they expected to arrest all but two ring-members Tuesday night and Wednesday morning.