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Sammy Reagan has a diverse work experience spanning several industries. In 1981, they started at Reagan Buick as a salesperson and eventually became one of the owners, selling their interest to their brother in 2006. In 1990, Sammy Reagan opened an Oldsmobile franchise for Reagan Automotive Group, Inc, which became one of the top 30 in sales nationally before GM closed Oldsmobile. Sammy then bought a Mazda franchise and relocated it. From 2011 to 2016, Sammy Reagan served as Treasurer at Diocese Of Nebraska. In 2015, they worked as the General Manager at Jet Linx. Since 2012, Sammy Reagan has been self-employed, managing rental properties, flipping houses, and building houses with Huber Builders. Most recently, they became President/Owner of Dorglass Inc in 2016.

Sammy Reagan attended General Motors Sales Management University from 1986 to 1988, where they studied Automotive Dealership Management. During this time, Sammy did not obtain a degree. Prior to that, from 1977 to 1978, Sammy graduated with a Diploma from Millard High School. They have also received a certification as a Graduate of General Motors Sales Management, although specific details regarding the institution and the year of achievement are not provided.