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Reggie Olson is a white-haired man who leases and sells horses, and hosts horse shows in Wiggins.

Anna and her family originally leased Acorn from him, before she was able to buy Acorn. Mr. Olson has a big horse farm on Crosshill Road, where he leases and sells horses to many people in the Wiggins area. His farm has three paddocks with horses and ponies, and a yellow barn with clean, brightly lit horse stalls. He likes to show off a computer program where he can type in any horse or pony's name, and there will be a record of who has previously owned or leased the animal.

His farm hosted the Wiggins Horse Show which the Pony Pals competed in.

Mr. Olson is the knowledgeable about what price to give a horse or pony. When Lulu wanted to buy Snow White from Rema Baxter, Rema got a fair price from Mr. Olson, and was going to sell Snow White to another girl, but decided to sell to Lulu in order to get the money right away.

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