It's been going on since 2005, police said.
Police said the ring, a multi-tiered crime organization that allegedly included mechanics and two commercial garages, has cost Manitoba Public Insurance (MPI) an estimated $800,000.
Authorities believe scam artists rolled back vehicle odometers, issued fake sales documents, created fake stolen-vehicle reports and staged collisions in order to make money from about 60 vehicles.
"This group is big, the number of vehicles is big, the numbers of dollars is big," said Tim Arnason, director of MPI's special investigations unit. "The scope of it was a bit surprising."
A 10-month investigation involved MPI investigators who worked with the Winnipeg Police Service commercial crime unit.
MPI paid out $650,000 in claims in connection with the ring. Thre were outstanding claims of about $150,000 that will not be paid.
MPI will sue the alleged fraudsters to recover payouts, Arnason said.
Last week, police executed search warrants at three homes on Tilstone Bay, Guay Avenue, and Killarney Avenue, and commercial garages on Nairn Avenue and in Selkirk.
Police have not identified the garages they believe are involved.
Twenty-one people were arrested and charged while warrants were issued for five more suspects.
Police said they anticipate more arrests and charges in the coming weeks.
"On this scale, with this many people, that's pretty unique," Winnipeg Police Service Det.-Sgt. Sandra Martin said.
She said the fraud ring operated in a hierarchical structure that mimicked a legitimate business, with layers of employees who answered to higher figures in the chain.
"When you're running something for four or five years and on this scale, you need that level of communication and organization in order to get the business done," she said.
Last November, an MPI employee noticed a vehicle that had strange damages that weren't consistent with a crash report, Arnason said.
That led investigators to a ring of people selling used luxury cars that had bogus odometer readings for inflated prices, among other suspected criminal activities.
The owner of one of the garages involved is charged with fraud, Arnason said.
Arnason said the alleged scammers imported the high-end vehicles into Manitoba. The vehicles were mostly high-end sports utility vehicles and passenger cars such as Cadillacs, Lincolns, BMWs and Mercedes.
If totalled in a crash, Arnason said, later models of those vehicles command a good price: "They have good value."
Investigators believe the ring also involved mechanics who manipulated information on certificates of inspection.
Martin said officials believe that one or two individuals involved in the ring have links to street gangs.
"Generally speaking, it's a Manitoba operation," Arnason said.
Charged are: Quincy Adurogboye, 29; Michelle Garand, 51; Jasmyne Garand-Jones, 21; Savanna Lughas-Garand, 19; Kaela Perry, 23; Maria Austria, 31; Norman Beardy, 40; Drazen Bukvic, 20; Feleshia Inglis, 23; Stacey Gerbrandt, 22; Elmer Fakhruddin, 23; Ray Ostertage, 52.
Police said there are nine others arrested and charged who have been released from custody on a court summons or a promise to appear.
Police are looking for Lamont Sesay, 27; Danielle Bruyere, 20; Serge Myron, 30; Kevin Arrow, 33 and William Franck, 54. Warrants have been issued for their arrests.
Approximate number of WPS officers involved in executing warrants last week
Number of MPI investigators tasked full-time since last fall to the project
Approximate number of alleged fraudsters who were known to MPI before the bust
Approximate number of vehicles involved in the alleged fraud ring
People who are still wanted on arrest warrants
Total amount of claims made by the alleged scam artists