Brown won the Beverly D Stakes with Sistercharlie, who led home stablemates Fourstar Crook and Thais for a one-two-three while Robert Bruce and Almanaar ensured he provided the first two home in the Arlington Million.
The other Grade One on the card, the Secretariat Stakes, saw Tom Morley’s Carrick spring a surprise when beating Analyze It.
Dermot Weld’s Bandua earned the best placing of the Europeans, just holding off Mick Halford’s Platinum Warrior in the Secretariat. Aidan O’Brien’s Hunting Horn and Lucius Tiberius were unplaced while Joseph O’Brien’s Ming finished sixth.
Mark Johnston’s Nyaleti finished sixth in the Beverly D, one place ahead of Aidan O’Brien’s Athena while in the Arlington Million Simon Crisford’s Century Dream crossed the line third but was demoted to fourth.
Deauville, running in the race for the third time, could only manage sixth for Ballydoyle with Jane Chapple-Hyam’s Circus Couture last of the eight finishers.
Robert Bruce earned himself an invitation to the Japan Cup following his win in the feature, which takes place just 22 days after the Breeders’ Cup for which he also earned his ticket.
The winner could have one more outing before taking in the Breeders'Cup, which is at Churchill Downs on the opening weekend of November.
“He’s got an unbelievable kick (Robert Bruce), but so did the losing horse," Brown said.
"They both ran tremendous.
“I may run him once before the Breeders’ Cup, possibly the Joe Hirsch (Turf Classic at Belmont Park on Sept. 29).”
Chilean bred, he was a star in his homeland before joining Brown.
“I’m very glad," owner Carlos E. Lavin said.
This is unexpected. To breed a horse in Chile and come all the way to Chicago to win this great prize is really wonderful. I’m very glad to be in Chicago, nice city and nice people.”
“We brought him here because we could not sell him here.”
On Century Dream's demotion, William Buick said: “Simon was always very confident of riding a horse positively and he’s real honest game horse and I thought there was a chance that everyone was going to be looking at each other and that no one really wanted the lead. WE were kind of an underdog in the race so I figured we’d try our best and make something of it.”