Early Wynn

Baseball Player

Early Wynn was born in Hartford, Connecticut, United States on January 6th, 1920 and is the Baseball Player. At the age of 79, Early Wynn biography, profession, age, height, weight, eye color, hair color, build, measurements, education, career, dating/affair, family, news updates, and networth are available.

  Report
Date of Birth
January 6, 1920
Nationality
United States
Place of Birth
Hartford, Connecticut, United States
Death Date
Apr 4, 1999 (age 79)
Zodiac Sign
Capricorn
Profession
Baseball Player, Journalist
Early Wynn Height, Weight, Eye Color and Hair Color

At 79 years old, Early Wynn has this physical status:

Height
183cm
Weight
86.2kg
Hair Color
Not Available
Eye Color
Not Available
Build
Not Available
Measurements
Not Available
Early Wynn Religion, Education, and Hobbies
Religion
Not Available
Hobbies
Not Available
Education
Geneva County (Geneva County, AL)
Early Wynn Spouse(s), Children, Affair, Parents, and Family
Spouse(s)
Not Available
Children
Not Available
Dating / Affair
Not Available
Parents
Not Available
Early Wynn Life

Early Wynn Jr. (January 6, 1920 – April 4, 1999), also known as "Gus," was an American right-handed pitcher.

During his 23-year MLB career, he played for the Washington Senators, Cleveland Indians, and the Chicago White Sox.

Wynn was dubbed one of the game's most intimidating pitchers, with a hardball and a stern attitude toward batters.

In 1972, he was inducted into the Baseball Hall of Fame. Wynn joined the Senators at the age of 17, deciding not to complete his high school education in search of a baseball career.

He played in Minor League Baseball for a few seasons (MiLB), with 1939 completing a brief MLB stint.

Wynn made it to the big leagues in 1941, pitching his first complete MLB season in 1942.

Wynn spent most of 1945 and a part of the 1946 season while in the United States Army during the later part of World War II. While with the Indians in the mid-1950s, Wynn was one of baseball's best pitching rotations, as well as Bob Feller, Mike Garcia, and Bob Lemon.

He received the 1959 Cy Young Award, but as the pitch speed diminished, he began to rely more on the knuckleball.

Following the 1963 season, Wynn retired.

He had won only 300 victories in his career, despite spending the last few months of his life in the hunt for the victory. After retiring as a player, Wynn served as a mentor and broadcaster in the big leagues.

He was listed on the 100 Greatest Players in baseball history in 1999.

Following heart-related issues and a stroke, Wynn died in an assisted living facility that year.

Early life

Wynn was born in Hartford, Alabama, in the son of Blanche Wynn and Early Wynn Sr., an auto mechanic and former semi-professional baseball player. Wynn referred to his ancestry as being Scottish, Irish, and Cherokee; sportswriter Lew Freedman suspects that Wynn was no more than 11,000 Cherokee. Wynn lifted 500-pound bales of cotton one summer for ten cents an hour, but the knowledge made him want to make a different life for himself. Wynn, who excelled at both football and baseball, was expected to be the top running back at Geneva County High School as a sophomore but suffered a broken leg during a punt return last year. Because of his football injuries, he was forced to suspend football and concentrate on baseball. Later, Wynn referred to it as "my best break ever."

Wynn appeared at a tryout session for the Washington Senators in Florida when he was a student. He impressed Senator Clyde Milan enough that the club offered him a minor league contract. Wynn has signed with Washington for $100 a month and has decided not to complete high school. Wynn played minor league baseball in the Florida State League and the Piedmont League between 1937 and 1939.

Later life

Following his retirement, Wynn joined the Indians as their pitching coach in 1964. Several of Sam McDowell's players, including Sam McDowell, Sonny Siebert, Luis Tiant, and Steve Hargan, were still with the team in 1967, where they set a record for team strikeouts in a season with 1189. Tommy John called him "abrasive" and not "very helpful," although Wynn did show John how to throw a slider. Wynn entertained the prospect of returning to form as a knuckleball pitcher in August 1965. Wynn left Cleveland after the 1966 season and joined the Minnesota Twins as pitching coach. He later served as the Twins' minor league manager. Wynn advocated for better pensions for veteran baseball players both on the track and off the field.

In 1970, Wynn suggested a one-game return to the Twins. If Ted Williams, the Twins, a retired star, would pitch one inning in 1972. Wynn would have been the first player to pitch in five different decades if the move had been made, but Williams was disinterested, and the team scrapped the idea. Williams dubbed him "the hardest pitcher I've ever encountered."

Wynn was inducted into the Baseball Hall of Fame in 1972, alongside Sandy Koufax and Yogi Berra. He was dissatisfied that he did not get the required votes on his first three ballots, but he was thankful for the opportunity. "I'd been hoping for it," he said, "I didn't want to set up my hopes too high." "It's like being placed on a pedestal rather than getting a gold watch for your long-awaited efforts." It's recognition that I was waiting for a long time."

Wynn authored the color commentary for radio broadcasts of Toronto Blue Jays games from 1977 to 1981, as well as Tom Cheek. He also provided color commentary for Chicago White Sox radio broadcasts in 1982 and 1983, partnering with Joe McConnell. When Wynn was traded by Lorn Brown in December 1983, White Sox president Eddie Einhorn described him as "a link to baseball's history."

Wynn suffered from a heart attack and a stroke in the last years of his life. Since the death of his second wife in 1994, his health had declined. He died in April 1999 in Venice, Florida, where he died. Wynn's body was cremated, and his family preserved his ashes.

Wynn was named one of 37 members of the Baseball Hall of Fame in 2013 for his service in the US Army during World War II.

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Early Wynn Career

MLB career

Wynn made his Major League Baseball (MLB) debut in 1939, when the Senators called him up in September. In a 4–2 loss to the Chicago White Sox, he threw a complete game in his first outing on September 13, giving four runs (three earned). Wynn made three starts in the minor leagues, with a 0–2 record and a 5.75 earned run average (ERA) before returning to the minor leagues in 1940 and 1941. "Wynn was not yet ready for major-league action," the Society for American Baseball Research's David Fleitz said. When he was again a September call up, he made it back to the major leagues in 1941. He gave up two runs and six hits in his first big league victory over the Philadelphia Athletics in his second game of a doubleheader against the Philadelphia Athletics. He played five games this season, winning four of them and ending with a 3–1 record and a 1.58 ERA.

For the first time since 1942, Wynn was named to Washington's four-man pitching rotation and spent the entire season in the major leagues for the first time. On April 30 against the White Sox, he threw a shutout, allowing the Senators to win by just one run. He gave up several runs against the New York Yankees in their second game of a doubleheader against the New York Yankees on September 6, but only five runs were earned. The Senators lost by 15–2. He appeared in 30 games during the season, leading to a 10–16 record and a 5.12 ERA. The 16 losses were ranked fifth in the American League (AL).

Wynn was the second starter in the Senators' rotation in 1943, behind Dutch Leonard. As Philadelphia defeated the Senators 2–1 in 16 innings on April 27, he threw 13 scoreless innings but got a no decision. In a 4–0 victory over the Cleveland Indians on July 10, he allowed only four hits and threw a shutout. On August 18, he pitched 13+13 innings, losing the game 3–2 to the White Sox in the 14th, but the two runs Wynn had allowed before were unearned. Wynn scored his first major league home run against Bob Muncrief four days later in the second game of a doubleheader against the St. Louis Browns. As the Browns defeated 8–5, he was less effective on the field, allowing seven runs in six innings. In a 5–0 victory, he held Philadelphia to three hits on September 10. In the first game of a doubleheader against the Yankees on September 19, Wynn gave up two runs in ten innings as the Senators defeated 3–2. He went 18–12 with a 2.91 ERA and 89 strikeouts, leading the AL with 33 starts in 37 games. In AL Most Valuable Player (MVP) voting, Wynn came 18th.

Wynn threw a two-hit shutout against the Philadelphia Athletics on April 20, 1944. In a 5–3 victory, he held the Indians to three runs (two earned) over 13 innings on May 26. In a 1–0 victory, he threw a four-hit shutout against the Boston Red Sox on June 18. He had a 6–7 record going into June 29, but he'd lose ten decisions in a row from that date and into August 13, when he finally won another game. On July 4, Wynn had held the White Sox to two runs in 11 innings; he gave up his third run in the 12th; and Chicago defeated Washington by a score of 3–2. Despite the fact that his season came to an end in late August, he was one of the league's worst losses in 1944, compiling an 8–17 record and a 3.38 ERA.

Wynn's 1944 season came to an end early, after he joined the United States Army on August 21. He completed 17 weeks of training at Fort Knox before heading to the Philippines to serve in the Tank Corps during World War II. Despite the fact that Wynn missed the 1945 major league season, he continued to play baseball, pitching for the Manila Dodgers, a Pacific Army unit.

Wynn, who was returning to the United States in June 1946, was able to resume pitching for the Senators on July 16. In the first game of a doubleheader on September 8, he pitched 11 innings against the Yankees, conceding just one run (unearned) and winning by only one run (unearned) and winning by Washington's 2–1 victory. He had an 8-55 record and a 3.11 ERA in 17 games this year.

Wynn was the Senators' Opening Day starter in 1947. He came within one out of finishing the first game of his season on April 23, but not before defeating Philadelphia in a 4–3 victory. In a 3–0 victory over the Indians on June 5, he shut them down. Wynn was brought back to the 1947 AL All-Star squad for the first time as a replacement for an injured Bob Feller, but he did not pitch in the AL's 2–1 victory. In the first game of a doubleheader on July 10, he gave up ten hits but then threw a shutout in a 4–0 win over the White Sox. In a 6–1 win over the Detroit Tigers on July 22, he allowed up only two hits and one run (unearned). He played 33 games this year and earned a decision in almost every game, winning 17 games with 15 losses and a 3.64 ERA. He came in 23rd in AL MVP voting after the season.

In 1948, Wynn got the Senators' Opening Day off again, but the Senators lost by 12 runs (10 earned) over 8+13 innings. The Senators beat the Indians by a score of 5–0 on May 6, limiting Cleveland to three hits in a shutout. By the end of June, he had a 7-7 record, but he only won one more game the rest of the season (against the Indians on August 29), losing 12 games and a 6.96 ERA in the season's second half. Wynn was the victim of inconsistency in 1948, with an 8–19 record and a 5.82 ERA. He earned 128 runs in his debut and his 19 losses were third in the league (behind Fred Sanford's 21 and Bill Wight's 20). He had a career-high 16 runs batted in Rookies, but he had a career-high 16 runs batted in (RBI).

The Senators made Wynn available for trade during the offseason. Johnny Pesky was traded from Washington for Wynn in November by the Boston Red Sox in November, but the deal did not go through. However, Bill Veeck, the Indians' president, had been trying to buy Wynn before the 1948 season began. In December, Wynn and Mickey Vernon were traded to the Cleveland Indians in exchange for Joe Haynes, Ed Klieman, and Eddie Robinson.

The Indians were excited about Wynn's potential, but they felt they needed more pitches to be truly successful. Despite throwing a changeup, Wynn relied almost entirely on his fastball and didn't have any other pitches available at his disposal. According to Fleitz, Pitching coach Mel Harder, a four-time All-Star with the Indians, taught Wynn how to throw a curveball, slider, and knuckleball; by the 1949 season, Wynn had the curveball and slider "mastered." "I could throw the ball when I got here [to Cleveland], said Wynn, "but Mel made a pitcher out of me." With Cleveland, he became a key part of Fleitz's "one of the best pitching rotations of all time," joining Feller, Bob Lemon, and Mike Garcia. They were later named by Cleveland manager Al López "the best pitching staff I ever saw in the majors," Cleveland manager Al López later said.

Wynn pitched all 11 innings of a game against the White Sox on May 28, allowing two runs as the Indians defeated 3–2. As the Indians led 8–1, Wynn held the Red Sox to four hits and one run on June 3. Interestingly, though Wynn was perfecting his new pitches as the 1949 season came to an end, he had more success earlier this year. He had a 7.61 ERA before July 17 and then put on a 4–6 record with a 4.62 ERA. In an 8–1 victory on August 2, he held his former team to one run. Wynn's 23 starts were his few in a season not interrupted by military service since 1941; he set an 11–7 record and a 4.15 ERA.

Wynn was the second starter in Cleveland's rotation by 1950, after Lemon and ahead of Feller (third). He made six appearances in a row from June 16 to July 9, including a game on July 9 in which he pitched five shutout innings of relief. In a 5–2 victory over the White Sox on July 6, Wynn thrashed a season-high 11 batters. In a 3–2 victory on August 14, he restricted the Tigers to two runs over ten innings. In a 1–0 victory, he held the White Sox to three hits and no runs. In his last game of the year, he shut down the White Sox, throwing six runs in a 2–0 win. He won 18 games and led the AL with a 3.20 ERA in 1950. Wynn reached the 100-strikeout record for the first time this year, with 143. It was the first of seven seasons in which Wynn would win at least 17 games in a row.

Wynn limited the Tigers to two runs in ten innings on April 18, 1951, defeating them 4–2. Despite a 3.62 ERA through June 17, Wynn's record was just 4–8; he won 16 games after that date to earn his first 20-win season. In an 8–0 victory, he held the Yankees to two hits and threw a shutout. Boston had scored four runs against him in 11 innings in 11 innings five days later, but Cleveland had a 5–4 victory over the 11th to defeat 5–4. He shuts down the White Sox in 4–0 victory in the first game of a doubleheader on August 19, a first game of a doubleheader. In a 1–0 victory over the Athletics on August 28, he held them scoreless. Wynn's win set six consecutive decisions beginning with his victory over the White Sox on September 25. Wynn tied for the AL lead in starts (34) and led the league with 274+13 innings pitched, tied for fourth (along with Ned Garver and teammate Garcia), second in strikeouts (133), behind only Vic Raschi's 164). In AL MVP voting, he came in 16th place.

In 1952, Wynn made his first Opening Day appearance as an Indian. On June 5, he held Boston to four hits, knocking out eight batters as the Indians defeated 5–0. Cleveland beat Detroit on July 4 in the first game of a doubleheader against Detroit. He only took two hits. Wynn was 16–9 by August 15, but he lost three appearances in a row to fall to 16–12 on August 24. He would not miss another game in 1952 after winning all seven of his final starts. In a 3–0 win on September 5, he held the White Sox to four hits. On September 12, he shut down the Red Sox for the third time, limiting them to three hits in a 5–0 victory. Wynn spent the year in various categories among AL leaders. He had the most home runs (23) and walks (132) of any AL pitcher, but his 2.90 ERA ranked tenth. His 23 victories came in second second place behind Bobby Shantz's 24, and his 153 strikeouts were topped only by Allie Reynolds' 160. Wynn placed fifth in AL MVP polling this season.

Wynn was the fourth starter in the Indians' rotation in 1953. In the first game of a doubleheader against the Senators on May 3, he allowed only three hits, striking out eight runs and then hitting a home run against Connie Marrero. In a 4–1 victory over the Yankees on June 28, he held the Yankees to three hits and a run, defeating Tom Gorman. In a 10–2 victory over the Yankees on July 23, he struck out seven runs and allowed two runs. On September 1, he had 10 strikeouts in eight innings against the Red Sox, giving three runs as the Indians defeated 13–3. He had a 17-12 record and a 3.93 ERA in 36 games (34 starts). His 17 victories ranked ninth in the AL, and his 138 strikeouts ranked third (behind Billy Pierce's 186 and Virgil Trucks' 149).

Wynn made the Indians' debut on Opening Day in 1954, his last of two appearances in the team's history. As the Indians defeated Gorman 10–2, he held the Yankees to two runs and drove in two runs himself against Gorman. In a 3–0 win, Wynn held the Tigers to two hits on May 28. In a 4–0 shutout victory over the Athletics on July 15, he held them to three hits. In a 4–0 victory, he threw a second shutout against Detroit on August 18, allowing six hits. He beat the New York Yankees 3–2 in their second game of a doubleheader against New York on September 12, defeating the 12 Yankees in a 3–2 victory. Wynn retired with a 2.73 ERA (fourth in the AL), played 23 games (most in the AL), and struck out 155 batters (second to Bob Turley's 185). He led the AL in starts and innings pitched and finished fifth in MVP voting, and was ranked sixth in MVP rankings. During 1954, the Indians won 111 regular season games, beating an AL record set by the 1927 New York Yankees and winning Wynn's first playoff appearance. Wynn started Game 2 against the New York Giants in the 1954 World Series. When the Giants beat the Indians 3-1, he allowed three runs in seven innings. That was Wynn's first appearance in the series as the Giants defeated Cleveland in four straight games.

Wynn didn't win his first match until May, being plagued by pneumonia to begin the 1955 season. On May 22, he threw a shutout against the Tigers, only allowing one hit when Fred Hatfield singled in the fourth inning. In a 5–0 shutout victory over the Baltimore Orioles on June 22, he struck out ten batters out of a 5–0 shutout victory. In a 5–0 win over the Yankees, he scored eight strikeouts and allowed only three hits in the first game of a doubleheader. When the Indians defeated the White Sox 1–0 on July 1, he threw his third shutout in a row. For the second time in his career, he was an All-Star and pitched three scoreless innings in the game. This was the start of eight straight All-Star Games, and it was decided to last six seasons. He had a 17-11 record and a 2.82 ERA in the 1955 season. Wynn's 17 victories were tied for fourth in the AL with Turley's 1.97 and Whitey Ford's 2.63), and his 122 strikeouts were ranked seventh in the AL (behind Pierce's 1.97 and Whitey Ford's 2.63). In addition, his six shutouts were tied for second, behind Billy Hoeft's seven. Despite the fact that he had never completed high school, Wynn Mill began writing a column for The Cleveland News named The Wynn Mill. He expressed his opinion about everything from umpires to Indians coaches, to Hank Greenberg's annoyance. Wynn contributed the column to the Elks Club in Nokomis, Florida, where he lived during the offseason.

On June 8, 1956, Wynn threw a shutout against the Yankees, allowing five runs in a 9–0 victory. In a 5–0 victory, he shut down the Red Sox on June 21, restricting them to four hits. He was struck in the chest by a quick line drive off the bat of Senator Jose Valdivielso on July 18, which was sparked by a sudden line drive. Wynn lost seven teeth from the crash, after being replaced by Hank Aguirre on the mound. The facial wound needed 16 stitches. In an 8-0 shutout, he was pitching again four days later, holding the Orioles to six hits. For the second time this year, he shut down the Yankees for the second time this season, allowing three hits in a 5–0 victory. In a 4–1 victory, he won his 20th game of the year with a ten-inning effort against the Kansas City Athletics. He finished second in the AL after 20 wins, behind Frank Lary's 21. Wynn placed third in ERA (2.72), behind Ford's 2.47 and teammate Herb Score's 2.53) and seventh in seventh with 153 strikeouts. Wynn was ranked 13th in AL MVP polling.

Wynn lost in the first game of a doubleheader against the Tigers on April 28, 1957, but he allowed just two runs and knocked out a season-high ten hitters. In a 2–0 shutout on June 27, he knocked out nine Yankees. In a 3–1 victory over Detroit in the first game of a doubleheader, seven days later, he had nine strikeouts once more, yielding three hits and one unearned run. On August 3, he struck out nine hitters as well, but the Yankees lost by 10 runs and four runs in seven innings. Wynn had 37 starts in the AL, but it was his first losing season with Cleveland in 1957. His record as an Indian was 14-17, and his ERA of 4.31 was his best ever as an Indian. He led the league in strikeouts (with a career-high of 184), but he also led the league in hits (270) and earned runs (126) allowed. Wynn and Al Smith were traded to Minnie Mioso and Hatfield by the Chicago White Sox at the start of the season. The trade brought him and López, who had worked with the Indians for the entire 1956 season, together.

Wynn's latest White Sox contract forbids him from writing for newspapers (thus ending The Wynn Mill), but his compensation was increased to compensate for lost income. Wynn threw a two-hit shutout against Cleveland in his first match since the trade. He held the Orioles scoreless on May 23, the White Sox's minimum for the White Sox to win 1–0. In a 4–0 victory, he gave up only two hits against Boston on June 19. In a 3–0 victory over Detroit, he delivered another two-hit shutout on August 31. On September 9, he had a winning record but dropped three of his last four starts to finish the year with a 14–16 record. Wynn became the first MLB pitcher to lead his league in strikeouts in a row (184 with Cleveland, 189 with Chicago). His ERA was 4.13.

"Everything clicked for both Wynn and the White Sox" in 1959, Fleitz writes. Since his fastballs were losing velocity, he started relying more on the knuckleball. "They've been accusing me of throwing it since I didn't even know how to hold it." I can't throw as much as I did six, seven years ago. And I get sore. "I find that throwing the knuckler with a little more effort and no strain," Wynn said. Wynn was the second pitcher in major league history to win a game 1–0 after posting at least ten strikeouts and hitting a home run on May 1, 1932; the Yankees did the same for the Yankees. In addition, he allowed just one hit to Boston in the game. On July 7, Wynn was the starting pitcher in the first All-Star Game of the year, allowing one run in three innings and a no-decision as the National League defeated the AL 5-4. On August 9 (second game of a doubleheader) and August 13, the White Sox won both games 9–0, with a back-to-back shutouts. As Chicago defeated the Athletics 3–2, he pitched ten innings on September 8, giving two runs to the Athletics. Wynn won by a 21st victory on September 22, the White Sox's AL pennant championship was clinched. Wynn won the Cy Young Award in 1959 at the age of 39, a record of 22–10, with 179 strikeouts and a 3.17 ERA. Following Cy Young and Grover Cleveland Alexander, he became the third-oldest MLB pitcher to win 20 games in a season. Wynn's 22 victories dominated the AL, his 3.7 percent strikeouts were third, behind Jim Bunning's 201 and Camilo Pascual's 179), and his 255+229 innings pitched led the league, with his 37 starts tied Paul Foytack for most in the AL. With five shutouts, he came in second, one less than Pascual's total. Wynn came in third in AL MVP voting, behind Nellie Fox and Luis Aparicio.

According to Sports Illustrated, Wynn was "magnificent" in Game 1 of the 1959 World Series. The Los Angeles Dodgers allowed no runs, just singles, to the outfield before missing because of the cold weather was affecting his elbow; the White Sox beat Los Angeles 11-0. He held the Dodgers scoreless for the first two innings but allowed four runs (three earned) in the third inning before being replaced by Turk Lown with two outs; the Dodgers lost the game 5–4, but Wynn had a no-decision. In Game 6's third innings, Duke Snider gave up two runs in the third inning but then allowed three runs in the fourth inning, ending the Dodgers' 9–3 loss.

Wynn shut down the Indians in their first game of a doubleheader on May 15, 1960, limiting them to five hits in a 4–0 victory. He lost five straight decisions from May 25 to June 18, but he did 11 of his next 15. Wynn was named to the All-Star Games for his seventh and last year, pitching two scoreless innings in the second All-Star Game in which the AL defeated the AL 6–0. Chicago defeated Kansas City by a score of 10–0 on August 19, shutting down the Athletics while the Athletics shutting down seven hits. In September, his last two victories of the season were decided within 12 days of each other, the first coming in a 1–0 win over Boston on September 11. He had a 13-12 record (his fewest victories since 1949), a 3.4 ERA, and 158 strikeouts, the third-highest total in the AL (behind Bunning's 201 and Pedro Ramos' 160). With four shutouts, Wynn tied Ford and Jim Perry for the AL lead in shutouts.

On May 12 and May 16, 1961, Wynn recorded a season-high seven batters in back-to-back victories. On July 22, he was scoreless and pitched seven shutout innings with six strikeouts, but the White Sox were denied by a no-decision, with the White Sox winning 7-4. Wynn was 8-2 in 1961, but his season came to an end against the Orioles because his gout, which had plagued him since 1950, was still too heavy for him to pitch through. He had 64 strikeouts and a 3.51 ERA. Wynn skipped the remainder of the season, even giving up eating meat in an attempt to get the ailment under control.

Wynn had started pitching mainly with the slider and the knuckleball by 1962. He was the oldest player in the AL at that time. Facing the Indians on May 28, he threw a three-hit shutout after Chicago defeated 2–0. In a 7-0 victory over Cleveland, his next victory (over a month later) was a shutout. He struck out eight batters and allowed only five hits. In a five-hit, 6–0 win over the Washington Senators, Wynn had another shutout 24 days later. In 1962, he hit a 7-15 record (his highest since 1948) with a 4.2 ERA (his highest since 1948) and only 91 strikeouts. The 15 losses were tied for fourth in the AL, with Don Schwall's total score touching fourth in the AL, and his 4.46 ERA was 0.49 above the league average. The White Sox cut him off early this season, thinking he was done.

Wynn had won his 299th match before 1962, and he was determined to win 300 more times in his career. In 1963, he attended spring training with the White Sox but was unable to make the team. He was offered one-game contracts by several franchises, but Wynn opted for a full-time contract, which he obtained from the Indians on June 21. Cleveland also added him to the starting rotation to give him the opportunities he needed. He failed to win in his first three appearances with the Indians in 1960, and the nine months and seven wins between any pitcher's 299th and 300th wins in MLB history are also long.

On July 13, Wynn struggled to sleep due to gout-related pain the night before his fourth start of the year against the Athletics. Wynn finally hit the big win in the outing. Ed Charles, the defending Kansas City batter, recalled Wynn's appearance: "His fastball, if it reached 80, is stretching it." He was adamant and yelled garbage, throwing nothing but bloopers and garbage." After pitching five innings, he left the game with a 5–4 lead. "Jerry Walker was able to save the game for me." Wynn recalled, "he was my roommate and pitched like a man possessed." Wynn reflected on his 300th victory, which came at the end of the 1963 season, long after his retirement, and said he was not proud of the achievement. "I had pitched a good game and gone nine innings, that would be something." But Wynn said that it isn't the way it was supposed to be. He is one of only 24 pitchers to win 300 games.

Wynn got off to a 3–2 win over Kansas City on July 27 to win (though Wynn was denied a no-decision because he was suspended from the game in the fifth inning). He made several relief appearances for the Indians before the season came to an end. He played his last of these on September 13, when he took on the Los Angeles Angels in relief of Jack Kralick, who was out for two outs in the sixth inning but runners on first and second. Wynn gave up an RBI single to Jim Fregosi and then got Charlie Dees to line out to shortstop to end the game. Wynn had been activated in favor of pinch-hitter Willie Kirkland in the bottom of the inning, but in the inning, he had pitched his last game. Wynn had a 1–2 record, a 2.28 ERA, and 29 strikeouts in 20 games (five starts). He resigned after the season.

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