The American magazine placed Hicks, who owns the Texas Rangers, in the top five following a series of disastrous transfer dealings.
His most high-profile hiccup, Alex Rodriguez, considered one of the best baseball players of all time, signed for the Rangers in 2000 for $252 million, then baseball's biggest deal.
Hicks was forced to trade A-Rod and his lucrative contract to the Yankees for little return. As part of the deal he agreed to foot some of the bill.
More head-scratching deals followed – none leading to success. Texas is the only franchise in baseball that hasn't won a playoff series.
Liverpool fans will be hoping this trend doesn’t follow at Anfield, although the £20 million purchase of Robbie Keane would suggest otherwise.
After a disappointing six months at Liverpool the striker re-joined Tottenham Hotspur on the last day of the winter transfer window for £12 million.
The Dallas Stars chairman owns 50 percent of the Merseyside club, much to the dismay of many fans.
Hicks, who is worth an estimated $1.3 billion, bought the club in February 2007 for £218.9 million in a joint deal with George Gillett; a relationship, which has since soured.
Rafa Benitez, who ended speculation about his future by signing a new long-term deal in March, was believed to be concerned by the fractured relationship between Hicks Gillett.
Hicks claims that any such problems between the two Americans has now been resolved and they are united in their forward-looking vision for the club.
The Texan maintains the long-term aim of the club is to build a new stadium once the economic climate has settled.
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