07/10/2008 12:00AM

Tin Cup Chalice attempting first route

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The big unknown for the undefeated Tin Cup Chalice is the stretchout to two turns as he goes after the second leg of OTB's Big Apple Triple as a heavy choice in the $150,000 New York Derby at 1 1/16 miles on Saturday at Finger Lakes.

Tin Cup Chalice has won all five of his starts, by a combined 31 lengths, most recently the seven-furlong Mike Lee Stakes on June 22 at Belmont Park, the first leg of the Big Apple Triple. That's as far as he has raced.

But as Tin Cup Chalice's breeder, co-owner, and trainer, Michael Lecesse, points out, the gelding's half-brother Don Corleone won the New York Derby in 2004, and he has a filly sibling, Two Reigns, who also won at a route.

After crossing the finish in the Mike Lee, with an eye toward the New York Derby, jockey Pedro Rodriguez asked Tin Cup Chalice to keep on running.

"Pedro galloped him out after the Mike Lee, and he said he thinks he'll be okay going two turns," Lecesse said. "So far he's been up to every challenge.'

Named after the Jimmy Buffett song "Tin Cup for a Chalice," Tin Cup Chalice faces five rivals Saturday.

Best among them, or at least the one Lecesse fears most, is Alexandros, who ships up from Belmont for trainer Del Carroll and will be ridden by Finger Lakes leading jockey John Davila, Jr.

Alexandros has 2 wins in 14 starts, but both were at a route, and his last-out Beyer Speed Figure of 91 is second-best to Tin Cup Chalice's 97.

That'srightofficer, Almighty Silver, and Judge William also will travel up from Aqueduct or Belmont.

Tin Cup Chalice beat That'srightofficer by 2 1/2 lengths in the Mike Lee, but That'srightofficer was gaining a little late, and he has won at 1 1/16 miles. Tin Cup Chalice has yet to run against any of the others.

The Big Apple Triple is restricted to 3-year-old New York-breds and offers a $250,000 bonus for winning all three legs. The third leg is the Albany Stakes at Saratoga on Aug. 20. Introduced in 1999, the series has yet to be won.

"Last year our goal with Tin Cup Chalice was to win the Finger Lakes Juvenile, and we won it," Lecesse said. "This year the goal all along has been the Big Apple Triple."

So stay tuned.

* Three-time winner Afleet Alexander, trained by Michael Ferraro and ridden by Jeremias Flores, brings the top credentials into the six-furlong $50,000 Niagara for statebred 3-year-old fillies.