In 1927 he joined the Burlington Bees of the Class D Mississippi Valley League and batted .323 in 119 games. He was sold by the Bees to the Minneapolis Millers of the Class AA American Association and spent spring training of 1928 with that team before being optioned to the Nashville Vols of the Class A Southern Association where he batted .311 in 80 games with 10 home runs. In July 1928, he was sent to the Dallas Steers of the Class A Texas League where he batted .337 in 65 games to finish the season.
Oglesby spent the next four seasons with the Des Moines Demons of the Class A Western League and was batting .385 in his fifth year with the club (1932) when he was sold to the Los Angeles Angels of the Class AA Pacific Coast League. The 26-year-old batted .323 in 64 games to conclude the season.
Oglesby spent the next three years with the Angels. In 1933 he batted .313 with 20 home runs and hit in 44 consecutive games. He hit .312 with 15 home runs in 1934 and batted .350 while slugging 24 home runs in 1935.
Not surprisingly, Oglesby was drafted by a major league club for 1936. He joined the Philadelphia Athletics for spring training and was chosen by Connie Mack as his first baseman to replace Jimmy Foxx who had been traded to Boston. Oglesby made his major league debut on opening day April 14 against the Red Sox at Fenway Park. Batting sixth in the line-up he went 2-for-4 with a base on balls. He was 0-for-4 in his next appearance against the Red Sox and was 0-for-3 in his final game, against the Senators, on April 17. A spike wound to his left hand that became infected kept Oglesby out of the line-up after that date and he didn’t play again for the remainder of the season.
In December 1936, he was sold by the Athletics to the Kansas City Blues of the American Association – a league he had briefly played in with Minneapolis back in 1928 and 1929. Oglesby, now 31, batted .306 with the Blues and joined the Buffalo Bisons of the Class AA International League in 1938. Over two seasons with the Bisons he batted .319 and .327, then joined the Albany Senators of the Class A Eastern League in 1940. In March 1942, after two seasons with Albany, the 36-year-old was acquired by the Little Rock Travelers of the Class A1 Southern Association. Continuing to be a useful hitter, he finished the year with the Memphis Chicks of the same league.
Oglesby entered service with the Army in 1943 and was based at Camp Wheeler, Georgia. Playing first base for the Camp Wheeler Spokes throughout the summer of 1943, Oglesby played alongside Cecil Travis, Ken Jungels and Walt Brickner. The Spokes had an outstanding year and clinched the National Baseball Congress Semi-Pro tournament title with a 5-3 win over Enid Army Flying School of Oklahoma on August 29. Oglesby was the tournament’s leading hitter.
By 1944, Oglesby was out of military service and managing the Atlas Electric semi-pro team in Tulsa, Oklahoma.
Oglesby made a return to organized baseball in 1947, working for the Chicago Cubs organization as the manager of the Sioux Falls Canaries of the Class C Northern League, leading them to a second place finish in the regular season and the post-season championship. In 1948, the Canaries dropped to seventh place and he was appointed manager of the Springfield Cubs who were expected to play in the Western Association, but when that team failed to secure a place in the league, Oglesby was appointed manager of the Janesville Cubs of the Class D Wisconsin State League. However, he was forced to resign on June 9 due to ill health.
Oglesby returned to baseball in 1950 as manager of the Miami Eagles of the Class D K-O-M League but with the team in fifth place with a 30-32 record he was fired on July 6. “I’ve tried my best to field a winning ball club for Miami and I've played every game to win,” he said at the time.
Oglesby returned to his home in Tulsa, Oklahoma. Suffering from continued ill health he worked as a guard at the Douglas Aircraft plant in Tulsa. He died at his home on September 1, 1955 from a self-inflicted gunshot wound. Oglesby was 50 and is buried at Memorial Park Cemetery in Tulsa.
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