The shady side of the Indy 500 is really no different than any other sport really. There has been a cast of characters throughout the years though that have stood out. Those that really took the phrase “by any means necessary” to bathe in Indy 500 Glory. Most have well publicized stories while others flew under the veritable radar, no pun intended. Who were they? Let’s have a look.
Larry Curry
Larry Curry started out as as a racing mechanic in the 1970’s. He rose through the ranks as a chief mechanic and then team manager where he had his most success with Team Menard. Curry led the team to an IRL Championship in 1997 with Tony Stewart. Found guilty of embezzing more than a million dollars from team owner John Menard, Curry ended up in Federal Prison for two years. On a high note Curry was able to return to work in the Indycar series in 2005. Thanks to Tony George, Curry was hired to run his Vision Racing Team in 2005. He also managed the Dreyer & Reinbold team for five years as well as the Indianapolis Speedrome. He last landed at Harding Racing in 2017. Curry would pass away in May of 2020 at the age of 68.
John Paul Jr.
While John Paul Jr. helped his dad in the smuggling of marijuana as a teenager, the only thing he was really guilty of was not ratting on his father. The cost was a great racing career. From May of 1986 to October of 1988 Paul spent 30 months in prison. Paul started his career in sports cars. He first debuted in an Indycar at Road America in 1982. He showed both promise and speed driving for VDS Racing in 1983 in a year old Penske PC-10. Paul took his first Indycar win in dramatic fashion passing Rick Mears on the last lap of the Michigan 500. He finished that year with four top-five finishes and eighth in the points standings.
Due to his ongoing legal issues he never landed a solid ride. The creation of the Indy Racing League in 1996 revitalized his career and he would take a win in that series at Texas in 1998. He made seven starts in the Indy 500 with the best finish of seventh in 1998. Paul would pass away in December of 2020 from Huntington’s Disease. Truly one of the nicest, kindest gentlemen you could ever come across in the paddock.
The Whittington Brothers
Many people wondered how Bill and Don Whittington were able to find speed and fund their own racing team when they both showed up at the Indianapolis Motor Speedway in the early 1980’s. Those yellow cars with nothing but Whittington Brothers emblazoned on their engine covers. They would be joined by brother Dale at Indianapolis in 1982. He would start once, never taking the green flag after crashing with Roger Mears on the front straightaway before the green flag flew. Funded by drug money, both would be out of Indy by 1985. Their best finish in the “500” would come in 1982 with a sixth place finish for Don & and 16th place result for Bill.
In 1986 Bill plead guilty to income tax evasion and conspiracy to smuggle marijuana. He was sentenced to 15 years in prison. That same year Don would plead guilty to money laundering. He served 18 months. Don currently owns World Jet in West Palm Beach, Florida. Bill died in a plane crash in 2021. Their young brother Dale, who was never involved in his brothers drug smuggling ring, would die in 2003 of a drug overdose
Randy Lanier
The story of Randy Lanier is the most publicized story of criminal activity. Lanier has told story on various podcasts as well as a Netflix special, but it really deserves the Hollywood treatment. With eyes always on the Indy 500 Lanier was the last of the Blue Thunder Racing Team group to jump to Indycar. He followed the co-owning Whittington brothers to the Indy 500 making his debut in 1986. Lanier had a good, clean month of May finishing ninth and winning rookie of the year. Pretty impressive for a driver with just a lighting bolt on the side of his car.
Maybe it was the purchase of a brand new March and Lola with cash that gave him away. A crash in the 1986 Michigan 500 left Lanier with a broken leg. He then disappeared. Some thought he was dead. The feds finally caught up to him in October of 1987. Lanier would receive a sentence of life without parole till that decision was reversed. Lanier gained his freedom in 2014 and now works in South Florida showing up at race tracks from time to time. He wrote a book in 2021 titled “Survival of the Fastest: Weed, Speed & the 1980’s Drug Scandal That Shocked the Sports World” along with A.J. Baime.
‘Umbrella” Mike Boyle
The most interesting of those that walked the criminal line in auto racing is Mike Boyle. Sounding like something out of the movie “Goodfellas” Umbrella Mike Boyle was the head of Chicago’s IBEW. One of the most powerful union leaders in the nation. How powerful? In 1937, during a contract dispute, Boyle ordered some 30 bridges to be raised throughout the downtown area sealing it off on a Friday night. The dispute was quickly resolved.
The Chicago mobster had a passion for racing. When Boyle entered in the 1937 Vanderbilt Cup races, using a Miller, he was embarrassed by the European car makers. Not one to just accept his defeat Boyle did what any car owner would do. He would buy Maserati’s. That would be a difficult task, but not for Boyle. He sent his chief mechanic and engineer Cotton Henning over to war torn Italy to purchase a car from the Maserati brothers.
Boyle built the first super team with a shop just east of the Indianapolis Motor Speedway. His team would win the 1939 and 1940 Indianapolis 500 with Wilbur Shaw driving. Shaw would eventually become president of the Indianapolis Motor Speedway in 1946 after the Tony Hulman purchase. Mike Boyle ended his racing team after 1941 and went back to Chicago. Shaw would die in a plane crash in 1954 while Boyle would succumb to a heart attack in 1958.
You have to wonder if the powers that be in racing at the time knew the “behind the scenes” of these participants. Did Eddie Rickenbacker know of Mike Boyle’s shady side? Some say “yes”. One wonders if USAC, IMS President Joe Cloutier, or even those in charge in the CART series ever questioned how the Whittington’s or Randy Lanier were able to fund their programs. While not winning race teams they were fairly competitive at the time. Doing so with no sponsors on the cars. Will we ever see outlaws in the Indycar Series again? I don’t think so, but I suppose anything is possible.