In his prime, Evander Holyfield was one of the most recognizable names in boxing. Holyfield is the only four-time World Heavyweight Champion and holds a record of 44 wins out of 57 fights.
Holyfield was well-compensated for his wins as well. His personal website maintains that the boxer won more than $230 million in the boxing ring alone. But he hasn’t exactly held on to all of that money.
In the late 1990s, Holyfield founded the unsuccessful Real Deal Records, which folded by the early 2000s. In 2008, Holyfield was facing foreclosure on his $10 million home in the Atlanta suburbs as well as a fierce child support battle.
The child support fight continues right up until this week, as Holyfield was held in contempt of court Tuesday for refusing to pay more than half a million dollars owed.
At one point, Dick “Night Train” Lane had one of the most impressive rags to riches stories of all time. Born to a pimp and a prostitute in Austin, Texas, Lane was ultimately abandoned in a dumpster before being rescued by Ella Lane at the age of three months.
After a stint in the army, Lane found himself playing for the Los Angeles Rams and quickly became one of the most popular and highly paid football players in the 1950s. Throughout his career in the 1950s and 60s, the “Night Train” was so successful that in 1969, Lane was voted the best cornerback in the first 50 years of the NFL.
After retirement, however, Lane’s fame faded and after a series of bad investments and scams, the former star was ultimately reduced to living on an $800 monthly pension until he died of a heart attack in 2002. While Lane had three sons, he lived out his last days in an assisted living community, under the care of a retired construction engineer.
At one time, George Best was widely considered one of the greatest British football (that’s soccer for us Americans) players who ever lived. In fact, Best was one of the very first footballers to become a celebrity for their talent.
But Best developed a worsening case of alcoholism throughout his adult life, ultimately drinking much of his money away. At one point in 1981, when Best was visiting the United States for a game, he reached into a drunk woman’s purse and stole her money in order to continue paying for drinks. In 1984, he was jailed for drunk driving and assaulting a police officer, ultimately spending Christmas in jail.
By 2000, Best had serious liver damage and required a liver transplant. Because of his struggles with money, the operation was paid for by Britain’s National Health Service. Best continued to drink heavily after the transplant, ultimately dying of multiple organ failure in 2005.