Kelley has single-handedly resurrected the winning ways of historic Calumet Farm.

No. 8 Brad Kelley

1,000,000 acres (down 500,000 acres)
The publicity-shy Kentucky native ranks as this year’s biggest loser, thanks in large measure to a rare interview with The Wall Street Journal in which he confirmed that his landholdings totaled “about a million acres.” The bulk of that acreage is in West Texas, where Kelley snapped up more than 20 ranching operations. Most of those holdings are grouped under Kelley’s Texas Mountain Cattle Co. umbrella. Ranches farther west are owned by his Spanish Trail Land & Cattle Co. He also has smaller holdings in Florida, Hawaii, Tennessee, and Kentucky. In 2012, his Calumet Investment Trust paid almost $36 million for one of Thoroughbred racing’s most hallowed grounds, Calumet Farm (above), located adjacent to Keeneland Race Course in Lexington. Kelley leases the historic farm from the trust and bases his horse-racing operations there.