In the days when the Futurity in New York (whichever track) was the biggest purse on the continent by a factor of 5 or 10, many trainers deliberately TRIED to keep their best runners maidens, because maidens got a significant weight-break in the Futurity. They would give them racing experience by running with a stablemate and declaring to win with the other horse, which means that the better horse would be pulled up late to let the stablemate finish ahead of it. Sir Barton was kept a maiden for this reason and the ploy almost worked; he finished second in the Futurity. So he was still a maiden, but a very accomplished one, when he won the Kentucky Derby the next spring.
Just recently, the filly Hollywood Story was so busy placing in stakes races that she didn't get around to breaking her maiden until she won the Hollywood Starlet S (G1).
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