| The Bold Ruler Handicap | |||||||
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34th Running on Saturday, October 31, 2009 3 year olds & Up $150,000 added 6 Furlongs Grade: III |
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| Year | Horse | Wt. | Time | Owner | Trainer | Jockey | Value |
| 2009 | Le Grand Cru (4) | 115 | 1:22.19 | Judson L. Streicher | H. Allen Jerkens | Jose Lezcano | 90,000 |
| 2008 | Lucky Island (ARG)(4) | 115 | 1:09.14 | Shadwell Stable | Kiaran McLaughlin | Alan Garcia | 65,460 |
| 2007 | Songster (4) | 117 | 1:08.80 | Godolphin | Saeed bin Suroor | Edgar Prado | 64,440 |
| 2006 | Tiger (5) | 114 | 1:08.49 | Susan and John Moore | James A. Jerkens | Eibar Coa | 64,020 |
| 2005 | Uncle Camie (5) | 115 | 1:08 3/5 | Carmine Telesca and John and Marilyn Guerrera | Michael Hushion | Richard Migliore | 63,960 |
| 2004 | Canadian Frontier (5) | 111 | 1:08 4/5 | Mrs. E. Paul Robsham | Stanley Hough | Javier Castellano | 64,620 |
| 2003 | Shake You Down (5) | 115 | 1:08 2/5 | Robert L. Cole Jr. | Michael Luzzi | Scott Lake | 65,040 |
| 2002 | Left Bank (5) | 121 | 1:09 1/5 | Michael Tabor | Todd Pletcher | John Velazquez | 63,646 |
| 2001 | Say Florida Sandy (7) | 117 | 1:08 3/5 | John Rotella | Juan Serey | Joe Bravo | 65,520 |
| 2000 | Brutally Frank (6) | 115 | 1:08 3/5 | Sunny Meadow Farm | Mitchell Friedman | Shaun Bridgmohan | 65,880 |
| 1999 | Kelly Kip (5) | 123 | 1:07 2/5 | Hobeau Farm | H. Allen Jerkens | Jean-Luc Samyn | 64440 |
| 1998 | Kelly Kip (4) | 117 | 1:07 3/5 | Hobeau Farm | H. Allen Jerkens | Jean-Luc Samyn | 66120 |
| 1997 | Punch Line (7) | 122 | 1:08 4/5 | Althea Richards | William Turner | Robbie Davis | 64980 |
| 1996 | Lite the Fuse | 119 | 1:09 2/5 | Richard E. Dutrow | Richard E. Dutrow | Julie Krone | 64500 |
| 1995 | Rizzi (4) | 112 | 1:08 4/5 | Hobeau Farm | H. Allen Jerkens | Dale Beckner | 64560 |
| 1994 | Chief Desire (4) | 117 | 1:08 3/5 | Charles G. Hagedorn | Michael E. Hushion | John Velazquez | 66300 |
| 1993 | Slerp (4) | 119 | 1:09 | Allan L. Richie | Robert B. Hess | Jose Santos | 70200 |
| 1992 | Jolies Appeal (4) | 119 | 1:09 1/5 | John Thor | Gasper S. Moschera | Herb McCauley | 67560 |
| 1991 | Rousing Past (4) | 119 | 1:09 4/5 | Tri Noble Stable | Carlos F. Martin | Nick Santagata | 67200 |
| 1990 | Mr. Nickerson (4) | 119 | 1:09 1/5 | Robert H. A. Nixon | Mark J. Reid | Chris Antley | 66240 |
| 1989 | Pok Ta Pok (4) | 121 | 1:09 4/5 | Barbara Turner | William H. Turner Jr. | Richard Migliore | 67560 |
| 1988 | King`s Swan (8) | 123 | 1:10 1/5 | Alvin Akman | Richard Dutrow | Chris Antley | 172800 |
| 1987 | Pine Tree Lane (5) | 118 | 1:09 | Leonard D. Mathis | D. Wayne Lukas | Angel Cordero Jr. | 103680 |
| 1986 | Phone Trick (4) | 123 | 1:08 4/5 | Howell Wynne | Richard Mandella | Jorge Velasquez | 70680 |
| 1985 | Rocky Marriage (5) | 119 | 1:08 4/5 | Sidney L. Port | Robert Frankel | Angel Cordero Jr. | 51390 |
| 1984 | Top Avenger (6) | 121 | 1:09 4/5 | John Franks | Jack D. Ludwig | Antonio Graell | 55350 |
| 1983 | Maudlin (5) | 119 | 1:11 3/5 | Tartan Stables | Jan Nerud | Jerry D. Bailey | 49500 |
| 1982 | Always Run Lucky (4) | 123 | 1:09 2/5 | Rockwood Stable | John P. Campo | Jimmy Miranda | 49050 |
| 1981 | Dave`s Friend (6) | 123 | 1:09 3/5 | John Franks | Robert L. Beall | Anthony Black | 48510 |
| 1980 | Dave`s Friend (5) | l23 | l:09 4/5 | Robert L. Beall | Robert L. Beall | Vince Bracciale Jr. | 48690 |
| 1979 | Star De Naskra (4) | ll9 | l:09 l/5 | Carlyle J. Lancaster | Richard D. Ferris | Jeffrey Fell | 48420 |
| 1978 | Half High (5) | ll5 | l:09 2/5 | Leon J. Hekimian | Edward Coletti | Angel Santiago | 25665 |
| 1977 | Jaipur`s Gem (4) | ll3 | l:09 3/5 | Jacqueline Crotty | Philip G. Johnson | Jean-Luc Samyn | 22050 |
| 1976 | Chief Tamanaco (3) | ll4 | l:09 4/5 | Great Wolf Hill Farm | James Iselin | Angel Cordero Jr. | 2l750 |
BOLD RULER was foaled at Claiborne Farm on April 6, 1954. He was bred and owned by Wheatley Stable and trained by Jim
Fitzsimmons. The star of the Phipps’ family stable, Bold Ruler won his first five races as a two year old, including the
Youthful and Juvenile Stakes. As a three year old in 1957, Bold Ruler was named "Horse of the Year", winning 11 of 16 races, and earning $415,160. His only unplaced effort was a fourth-place finish in the 1957 Kentucky Derby.
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