Lolich was signed by the Detroit Tigers as an amateur free agent in 1958. After spending five seasons in the minor leagues, he made his major league debut with the Tigers on May 12, 1963 at the age of 22. Lolich blossomed in 1964, winning 18 games and 192 strikeouts in his first full season in the major leagues. In 1965, he posted a 14-14 won-loss record, but improved to 226 strikeouts, second best in the American League behind Sam McDowell.
In 1967, the Tigers hired former major league pitcher, Johnny Sain, as their pitching coach. Sain helped develop Lolich's pitching skills and taught him the psychology of pitching. The 1967 season was a memorable one due to the tight four-way pennant race between the Tigers, the Boston Red Sox, the Minnesota Twins and the Chicago White Sox. The Tigers remained in the pennant race until the final day of the season, finishing one game behind the Red Sox. Lolich finished the season with a 14-14 record, but led the league with 6 shutouts.
The Tigers began the 1968 season in first place, winning nine consecutive games after losing the season opening game. Lolich was overshadowed by teammate Denny McLain's 31-game win season, and was sent to the bull pen in August for poor performance. He made six appearances as a relief pitcher before returning to the starting rotation. Lolich had a 17-9 record with 197 strikeouts, as the Tigers led from start to finish to win the American League pennant by 12 games over the second-place Baltimore Orioles.
After Bob Gibson had defeated McLain in Game 1 of the 1968 World Series, Lolich helped the Tigers recover by allowing only one run to win Game 2 by a score of 8-1. He also helped himself at the plate, when he hit the first and only home run of his 16-year career. The Tigers lost the next two Series games to fall behind the Cardinals three games to one and were facing elimination when Lolich returned to pitch in Game 5. Despite an unsettled start, when he surrendered a two-run home run to Orlando Cepeda in a three-run first inning, Lolich remained calm and proceeded to pitch eight scoreless innings, as the Tigers scored two runs in the fourth inning, then went ahead in the seventh inning, when Al Kaline hit a bases loaded single to drive in two runs. The Tigers went on to win by a score of 5 to 3 to stave off elimination. The Tigers then won Game 6 aided by a good performance by McLain and a grand slam home run from Jim Northrup to force a crucial Game 7. With just two days of rest, Lolich would face Gibson in the final game of the series with both pitchers having won their previous two starts. Lolich and Gibson pitched six scoreless innings before the Tigers broke through to score three runs in the seventh inning. Lolich picked off Lou Brock and Curt Flood in the bottom of the sixth inning to extinguish a Cardinals threat and went on to pitch a 4 to 1 Tigers victory. Detroit became only the third team in World Series history to rally from a 3-1 deficit to win in Game 7. Lolich became the 12th pitcher to win three games in a World Series, and the last to win three complete games in one series. He was the last pitcher to win three World Series games until Randy Johnson won three games in the 2001 World Series. Lolich's performance earned him the World Series Most Valuable Player Award.
Lolich was a picture of consistency, winning 14 or more games for ten consecutive seasons, including 1971 when he led the American League with 25 victories (a total no subsequent Tiger pitcher has reached) and 22 in 1972. He struck out a career-high 308 batters in 1972, helping the Tigers to the American League East Championship that season while personally finishing runner-up in the Cy Young Award balloting. The 308 strikeouts is still the Tigers record for a single season. He also struck out 200 or more batters seven times during his career, and ranks third among left-handers (behind Steve Carlton and Randy Johnson) in career strikeouts with 2,832.
After suffering through the 1975 season, in which he lost 18 games for a declining Tigers team, the Tigers traded him to the New York Mets with outfielder Billy Baldwin in exchange for star outfielder Rusty Staub and pitcher Bill Laxton. In 1976, Lolich's slump continued with the Mets, as he won just 8 games while losing 13, leading him to retire. He returned to his home in suburban Detroit, opened a doughnut shop, and skipped the 1977 season. He eventually re-entered the free agent market, signed a contract with the San Diego Padres, and pitched for them during the 1978 and 1979 seasons before permanently retiring. At the time of his retirement, he held the Major League Baseball record for most career strikeouts by a left-handed pitcher. Lolich still holds the American League record for the most career strikeouts by a left-handed pitcher.
Lolich was deemed to be right-handed, but a tricycle accident that occurred while Lolich was young forced him to adapt to using his left hand. This would come to include baseball, once he began to play it. Although he became a left-handed pitcher, Lolich batted right-handed and still writes right-handed.
After Lolich's career ended, he continued to run his doughnut shop in Lake Orion, Michigan (a small suburb roughly 40 miles north of Detroit) for several years before he sold the business and retired. Today, he is active in charitable work and serves as a coach at the Detroit Tigers' fantasy camp in Lakeland, Florida. Because of his humble, "average man" qualities, he is still known to many long-time Tiger fans as one of the most popular sports figures in a working man's city. As the Detroit News put it, "He didn't act like a big shot superstar, he was one of us."
In 2003, Lolich was one of the 26 players selected to the final ballot by the National Baseball Hall of Fame's Veterans Committee. He received only 13 votes, placing him far below the 75% required for election. Lolich has often said the fact that he never won the Cy Young Award was a factor in not receiving sufficient votes to be elected to the Hall of Fame.
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