That is a lot of questions in one post....
Usually by the time horses get to the KY Derby they have a regular jockey but riders picking up a mount at the last minute is not uncommon. It can happen in any race of any level.
Mine That Bird was ridden in Canada by Chantal Sutherland. When he was purchased the new owners moved him to New Mexico and had Casey Lambert ride him.
They wanted someone with more experience to ride him in the Derby....reportedly Chantal was contacted by one of the owners and thought she had the ride...She did win on him at Woodbine but then never heard back.
As for trainers giving riders instructions, that is how it works. Not hilarious. The trainers are with the horses day in and day out. They are the boss. Jockeys who don't listen to them lose the rides. Any decent jockey knows to listen to the trainer.
Thoroughbreds are exercised daily but not at race speeds. How often they go that fast in training depends on the horse and the situation. Normally, exercise riders ride them in the mornings. Not jockeys unless they are extra special or the jockey up and coming/hungry for work. Usually the jockeys just show up for the races. They do not often bond with the horses, there are exceptions for sure.
Calvin rode MTB to win the Derby and then declined to ride him in the Preakness because he already had the mount on Rachel Alexandra, the filly who won the Kentucky Oaks the day before the Derby. Mike Smith took over on Bird but Calvin and Rachel won...
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