Jose Mourinho is believed to have been paid around £80million from being sacked by clubs in his career.
The 60-year-old was fired for the sixth time in his career after being dismissed by Roma on Tuesday.
Mourinho leaves after a disappointing season that has left the Italian side sitting in ninth in Serie A.
Chelsea have paid him more than £26m alone, with Mourinho having pocketed £18m when he was sacked at Stamford Bridge in 2007 and £8.3m following his second dismissal in 2015.
He was also given a £17m pay-off by Real Madrid and nearly £20m by Manchester United when he was binned in December 2018 – just months after he had signed a new two-year contract through to 2020.
An ill-fated 17-month stint at Tottenham also ended in the sack and a healthy £15m in compensation. He had another two years to run on his deal at Spurs when he was shown the door.
His payout from Roma is only likely to be around £3m, given he was out of contract at the end of the season.