After a decent rookie season with the San Jose Barracuda back in 2017, Middleton was rewarded with a fancy entry-level contract during the Rookie Showcase, and since then has proven that he is worthy of one.
His trek to the Top 25 Under 25 rankings has been an interesting one. The seventh-round draft pick in the 2014 Entry Draft by the L.A. Kings never signed an entry-level contract after an above-average season with the Ottawa 67s. Instead, Middleton settled for an amateur tryout with the Kings’ ECHL affiliate, the Manchester Monarchs. He then decided to forgo an overage year in the OHL, and was signed to an AHL contract by the Barracuda in 2016.