Sackinsky played for the United States national under-18 baseball team which went undefeated en route to a gold medal at the 1989 World Junior Baseball Championship in Trois-Rivières, Quebec.
Sackinsky played baseball at South Park High School in South Park, Pennsylvania. After high school, he played college baseball at Stanford. As a freshman, he pitched a complete game to win an elimination game against Georgia in the 1990 College World Series. Georgia had beaten them 16-2 in their previous game. Sackinsky was described by William C. Rhoden in The New York Times as "[p]erhaps the greatest surprise for Stanford" that season along with Jeffrey Hammonds.
He was selected by the Baltimore Orioles in the second round of the 1992 Major League Baseball draft. He was assigned to the Frederick Keys to begin his professional career but was demoted to the rookie-level Bluefield Orioles by August. In the fall of 1994, he played with Michael Jordan for the Scottsdale Scorpions in the Arizona Fall League. During the 1994–95 Major League Baseball strike, Sackinsky worked out with his former college baseball team before returning to stay at his parents' home in Library, Pennsylvania where he worked out with his former high school team. When the 1995 season began, Sackinsky took the mound for the Rochester Red Wings as the first pitcher in the history of Frontier Field. Sackinsky sat out nearly a month in the first half of the 1995 season due to elbow inflammation before undergoing surgery that summer.

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