Sinistra edged Big Business by a nose Thursday in the $100,000 Evan Shipman for New York-breds at Saratoga Race Course.
Trained by Karl Grusmark for owner-breeder Edward Shapoff, the 4-year-old Stonesider gelding came from just off the pace to run down 8-5 favorite Big Business and hit the wire in 1:51.96 for 1 1/8 miles on the muddy main track.
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Longest shot in a field of eight at 27-1, Sinistra paid $56, $15.60 and $6.60. Big Business returned $4.30 and $2.70, and Escapefromreality paid $3.50 for show.
In the co-feature, Makari outfinished Demonstrative to win the Grade 1 $100,000 A.P. Smithwick Memorial Steeplechase by a nose.
The 7-year-old gelding was making his North American debut for trainer Elizabeth Voss, who took over the family stable following the death of her father, Tom Voss, in January. Tom Voss was a two-time Smithwick winner, in 1997 and 2003.
Makari ran 2 1/16 miles in 3:48.33 and paid $11.60, $9.50 and $13.60. Demonstrative returned $17 and $18 for second, and pacesetter Pleasant Woodman held on for third to pay $22.40.