On June 2, 2025, Simon was claimed off waivers by the Pittsburgh Pirates. He made eight appearances for Pittsburgh, going 7-for-30 (.233) with two RBI and one stolen base. On August 30, Simon was placed on the injured list due to a dislocated left shoulder. He was transferred to the 60-day injured list on September 23, officially ending his season. Simon was designated for assignment by the Pirates on November 18. On November 21, he was non-tendered by Pittsburgh and became a free agent. On November 24, Simon re-signed with the Pirates on a minor league contract.
Founded Mindset Training in 2020 where provide students as young as 10 the experience of discipline, adversity and focus that will prove vital to their maturation in life.
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