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Three gambling firms owned by William Hill are to pay penalties of £19.2m for failing to protect consumers and weak anti-money laundering controls.
The record penalty comes after the Gambling Commission found "widespread and alarming" issues at the company.
The problems were so severe the commission had "seriously considered" suspending the firm's licence.
In one case, a customer was allowed to open a new account and spend £23,000 in 20 minutes without any checks.
As well as insufficient controls in place to protect new customers, the commission also found several failures to guard against possible money laundering.
It found cases where customers were allowed to deposit large amounts without the business conducting appropriate checks.
The commission said one customer was able to spend and lose £70,134 in a month, while another deposited £73,535 and lost £14,068 in four months.
"When we launched this investigation the failings we uncovered were so widespread and alarming serious consideration was given to licence suspension," said Andrew Rhodes, the Gambling Commission's chief executive.
"However, because the operator immediately recognised their failings and worked with us to swiftly implement improvements, we instead opted for the largest enforcement payment in our history."
Under the settlement, WHG (International), which runs williamhill.com, will pay £12.5m, Mr Green, which runs mrgreen.com, will pay £3.7m and William Hill Organization, which runs more than 1,300 betting outlets across Britain, will pay £3m.
The commission said the £19.2m collected from the penalties will go towards "socially responsible" good causes.