With one Grade 3 win as the high point on her resume, it took some convincing by trainer Shug McGaughey III and Daisy Phipps, the daughter of owner Ogden Mills Phipps, to enter his homebred in the 2005 Distaff. Pleasant Home came into the race off a second-place finish in the Grade 1 Spinster over a deep and tiring track at Keeneland. “Coming out of that effort and off of two sprints at Saratoga, I thought she got a lot out of it,” said McGaughey who was inducted into the Hall of Fame the previous year.
The presence of the 2004 Distaff and Eclipse Award winner Ashado sent half of the field into double-digit odds, with Pleasant Home at 30 to 1. The Phipps runner was 11th at the halfway point and while saving ground, swept past nine rivals on the turn. She then moved outside the leaders and pulled away to an amazing 9 1/2 length upset victory.