Mayor Francis Slay credited Calvert's involvement in the City's new Executive Order requiring Project Labor Agreements on large construction contracts. Mayor Slay explained to the Construction News and Review that he signed the order only after "Our lawyers said this was a good, legal way to do it." As City Counselor, Winston Calvert drafted the executive order. Although prior administrations and their city counselors had failed to find the way to craft a legal rationale for such an order, Calvert successfully defended it against legal attacks from inside and outside City government.
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