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There were nonetheless a number of particularly talented ballplayers who played in the league's twilight seasons. Third-baseman Jack Kubiszyn out of the University of Alabama capped a three year career in the league in 1957 leading the Kentville Wildcats to their first ever league championship. He later played 50 games in the major leagues with the Cleveland Indians. The following year saw two more Wildcats who would make it to the "show". Lee Elia eventually broke into the big leagues with the White Sox playing for manager Eddie Stanky. During spring training in 1966 Elia had been designated for assignment to the minors, but on the last day of the spring Stanky asked him to pinch hit against eventual Hall-of-Famer Bob Gibson. Elia clubbed the ball over the left-center field fence. After the game Stanky approached Elia and said, "you didn't quit on me, I'm taking you north with the club". Nicknamed "banty rooster" because of his determination and grit, Elia later made a name for himself as a major league manager, and is remembered in particular for an obscenity-laced tirade against Chicago Cub fans for booing their own ball club. Another player from the '58 Wildcats, Norm Gigon played briefly for Chicago as well, before joining former H&D leaguers such as Bill Brooks, Roger Rada, Bill Thurston, Joe Fulghum, Jack Stallings, and Moe Morhardt in collegiate coaching ranks.

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In the final years of the league's operation there were a number of players who graduated to the major leagues. Ralph Lumenti, the Truro fireballer, went directly from Truro to the majors at the end of the 1957 season, reminiscent of Moe Drabowsky the year before. Hal Stowe, who pitched for Halifax in 1958, had a cup of coffee with the New York Yankees, and Stellarton pitcher Jim Hannan of the same year eventually broke into the big time, appearing in over two hundred games between 1962 and 1969. Moe Morhardt who spent two seasons in Nova Scotia played briefly as a back-up to Ernie Banks in 1961. Players on 1959 league rosters who later toiled in the big leagues included Rollie Sheldon who starred for the Yankees in the early 1960s, pitcher Ed Connolly who went on to play for the Red Sox, and pitcher-outfielder Danny Murphy from the '59 Bearcats who broke in as an outfielder with the Chicago Cubs in 1960 and resurfaced for a second stint a few years later as a pitcher with the White Sox.
In addition to the players named above, local boy Vern Handrahan from Charlottetown, PEI went on to play in the majors in the expansion era. After playing in Stellarton in 1958, he was signed by Milwaukee scout Jeff Jones, who sent the nineteen year old for a tryout with Wellsville of the New York- Penn (NYP) league. Later he would move to the Kansas City organization, breaking in with the Athletics in 1964. Handrahan played two years in the majors, mostly as a reliever, and held major-league batters to a combined .242 batting average. Handrahan is one of only two Prince Edward Islanders to ever play major league baseball.