[1] Strickland also played for the Southwest Sectional champions representing his hometown at the American Legion Baseball World Series in Miles City, Montana in 1943.

[3][5] Immediately after the tournament, he signed with the New Orleans Pelicans, a Brooklyn Dodgers farm team at the time, and made his professional debut on September 5, 1943.

He was stationed as a Specialist Mailman for 16 months in Saipan after American forces had captured the island from the Imperial Japanese Army in July of the same year.

[14] In the top half of the opening inning of the 6–2 defeat in Game 3 at Cleveland Stadium, he committed a throwing error attempting to complete a double play, leading to the Giants' first run of the match.

He entered the contest with one out in the Boston eighth as a substitute at third base for Bubba Phillips, who was sent to left field to replace Jimmy Piersall, who had been ejected for arguing with home plate umpire Ed Hurley over his distraction of batter Ted Williams.

[3] He spent the following year on Sam Mele's coaching staff with a Minnesota Twins team that finished in second place, five games behind the eventual World Series Champion Yankees.

[1][12] He became the Indians' interim manager at the beginning of the 1964 campaign when Tebbetts suffered a heart attack near the end of spring training on April 1.

The Indians were in eighth place with a 33–39 record and thirteen games behind the league-leading Baltimore Orioles by the time Tebbetts returned to the club the next day.

[21] Strickland was called upon to lead the ballclub on an interim basis again after Tebbetts was dismissed on August 19, 1966, with the 66–57 team in third place and trailing the eventual World Series Champion Orioles by fourteen games.

"[23] When Strickland joined the Kansas City Royals coaching staff in 1970,[24] he was reunited with former Indians teammate Bob Lemon, who would be promoted to manager in early June.

[25] The most successful of the three years he spent in Kansas City was 1971 when the Royals vaulted into second place in the AL Western Division with an 85–76 record in only the franchise's third season of existence.