With a picture-perfect ride from jockey Joe Bravo, the 6-year-old son of Lemon Drop Kid rode the rail tracking the pace almost all the way around the grass course, angled out at the top of the stretch to pass the front-runners, and held off at late drive from Vyjack to win by a neck.
Fredericksburg set the pace, with Rose Brier applying pressure, clicking off fractions of :24.11, :47.46, and 1:10.38 through six furlongs. Middleburg moved up to third in the final turn, still saving ground, but was only seriously challenged by Vyjack. Rose Brier held gamely for third, three-quarter lengths back.
The Christophe Clement-trained Middleburg is a nose away from being undefeated on the Monmouth grass. He won the 2015 Cliff Hanger (gr. IIIT) and was a nose back in last year's Monmouth Stakes (gr. IIT).
"This horse is just so good," Bravo said. "We got the perfect trip in behind horses and he settled great. Around the turn we moved to the outside and he just ran those horses down. It's fun to ride ones like this."
The winner, the 2-1 second choice, hit the wire in 1:33.62 and paid $6.60, $3, and $2.20 across the board. Vyjack brought $4.80 and $2.80, and Rose Brier delivered $2.80 to show.
A Virginia-bred out of the Spectrum mare Rum Charger, Middleburg is a half brother to multiple grade I winner Winchester. He has a 6-8-3 record from 19 starts and earnings of $429,760.