Born in Arkansas, Winkles learned baseball under the tutelage of future Hall of Fame third baseman George Kell and played high school baseball with Kell's younger brother Skeeter who briefly played in the major leagues with the Philadelphia A's.
The Chicago White Sox would sign Winkles as a shortstop in 1951 after discovering him play at nearby Illinois Wesleyan University. Winkles would spend nearly the rest of the decade with the Chisox but never played higher than Triple-AAA. During this period, the White Sox would sign another shortstop Luis Aparicio who would win the 1956 AL Rookie of the Year en route to a Hall of Fame career. In 1958, while playing for the Indianapolis Indians, the team's manager Walker Cooper told Winkles, "There's only one thing keeping you out of the major leagues. Ability."
However, Winkles did have a mind for the game and not long thereafter a new door opened for Winkles. Arizona State University contacted Winkles and asked them to coach their baseball team which had long been the school's laughing stock. Winkles, now 29, heeded Horace Greeley's advice and went west.
In 13 seasons at the helm of ASU's baseball program, the Sun Devils went 524-173 (an astounding winning percentage of .752) and won the College World Series in 1965, 1967 and 1969. Winkles mentored several future big league players like Reggie Jackson, Sal Bando, Rick Monday, Gary Gentry and Larry Gura.
Had Winkles remained in the collegiate ranks he could have been the most successful college baseball coach ever. But to the shock of all, Winkles left ASU to join the coaching staff of the California Angels in 1972 under the team's new manager Del Rice. After a disappointing 75-80 finish in '72, the Angels fired Rice and promoted Winkles as manager. The Angels got off to a good start in 1973 and were in first place in the AL West in late June, but would swoon in July and finish fourth in the division with a 79-83 record despite having two 20-game winners in Nolan Ryan and Bill Singer. However, their offense was suspect outside of Frank Robinson and Bob Oliver.
The Angels would dismiss Winkles mid-way through the 1974 season amid clashes with Robinson. For his part, Winkles said he thought Robinson should become a big league manager. The following year, Robinson became MLB's first African-American manager when he was hired by the Cleveland Indians. Winkles would be replaced by Dick Williams, fresh off winning back to back World Series with the Oakland A's only to resign in protest of owner Charlie Finley's treatment of infielder Mike Andrews during the '73 Series.
Ironically, Winkles would find himself in Oakland not long after being dismissed by the Angels. New A's manager Alvin Dark named him third base coach reuniting him with his former ASU charges Reggie Jackson and Sal Bando. Winkles would earn a World Series ring as the A's won their third straight Fall Classic although he would only earn half a World Series share. He would remain on the A's coaching staff in 1975 as the team won it's fifth consecutive AL West title. But Finley would fire Dark, Winkles and the entire coaching staff after the A's were swept by the Boston Red Sox in the ALCS.
Winkles moved across the Bay and joined the San Francisco Giants coaching staff as the team's third base coach under Bill Rigney. He would remain in the job in 1977 after the Giants replaced Rigney with Joe Altobelli. However, in June Winkles would go back across the Bay and get a second chance as a big league manager by taking over the reigns of the A's as Finley moved Jack McKeon into the front office. By this time, however, the A's were shell of their former selves outside of rookie sensation Mitchell Page. The A's went 37-71 under Winkles and would finish in last place in the AL West even managing to finish a half game behind the expansion Seattle Mariners. The A's weren't expected to be much better in 1978.
While Winkles would never manage again, he would remain in the game for the next 15 years. Shortly after his resignation, Winkles would reunite with the Chicago White Sox and serve as a member of their coaching staff through 1981. White Sox GM would tab Winkles as the team's Director of Player Personnel in 1982 and served in this capacity before the next four seasons. In 1986, Montreal Expos manager Buck Rodgers asked Winkles to join his coaching staff. Winkles became acquainted with Rodgers a decade earlier while on the Giants' coaching staff. He would serve Rodgers as the Expos hitting coach in 1986 before coaching first base for the next two seasons. In his final five seasons with the Expos, Winkles went into the broadcast booth and served as a color commentator on their radio broadcasts before retiring after the 1993 season.
In 2006, Winkles was inducted into the College Baseball Hall of Fame. Winkles wrote a memoir in 2016 called From the Cotton Fields to the Major Leagues: Perspectives on a Baseball Life featuring a foreword by Reggie Jackson. I leave you with Winkles talking about his life in baseball. R.I.P.
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