The White Sox selected Ventura with the tenth overall pick in the 1988 amateur draft from Oklahoma State University (OSU).

He is a six-time Rawlings Gold Glove winner, two-time MLB All-Star selection and a National College Baseball Hall of Fame inductee.

While playing college baseball for the Cowboys at OSU, Ventura was a three-time All-American who achieved a Division I-record 58-game hitting streak.

In 1988, he won the Dick Howser Trophy and Golden Spikes Award and played for the gold medal-winning Olympic baseball team.

[5] Ventura helped OSU reach the finals of the 1987 College World Series, although they lost the championship game to a Stanford University team that included future teammate Jack McDowell.

[6] In January 2020, Ventura returned to Oklahoma State to complete his degree and serves as a student assistant coach for the baseball team.

He won both the Golden Spikes Award[8] and the Dick Howser Trophy for outstanding collegiate play, concluding his 3-year OSU career with a .428 batting average, a .792 slugging percentage, and 302 RBI.

He was named to the 1990 Topps All-Star Rookie Roster[citation needed] and earned the starting third base role with the White Sox the next spring.

[9] The next year he won his first Gold Glove Award for fielding excellence, set a team record for RBI at third base, and led the AL in putouts.

In a spring training game at Ed Smith Stadium, Ventura slid into home plate and caught his foot in the mud, suffering a compound fracture and dislocation to his right ankle.

His homer and RBI totals were close to his career averages, but the White Sox attempted repeatedly to trade him and declined to renew his contract, with owner Jerry Reinsdorf claiming that he was "deteriorating.

"[27] However, Ventura injured his left knee in August; when the problem finally came to light, just before the postseason, it had worsened into a tear of the cartilage.

[29] Despite his injury, Ventura provided the game-winning, bases-loaded, two-out single in the eleventh inning against the Pirates on the final weekend of the regular season.

[30] After sweeping Pittsburgh, the Mets defeated the Cincinnati Reds in a play-in game to determine the National League Wild Card team.

[31][32] In Game 5 of the 1999 NLCS, with the Atlanta Braves up 3–2 in the fifteenth inning, a bases-loaded walk to Todd Pratt forced in the tying run and brought Ventura to the plate.

He spent part of July on the disabled list with inflammation in his repaired shoulder,[38][39] and was plagued with errors; but rebounded to hit .320 with three homers and 13 RBIs in the last two weeks of the season.

[46] This set off a domino effect that ended in Ventura being relegated to a bench role as a backup infielder and pinch hitter.

Ventura made his pitching debut on June 25 during a blowout loss against the Anaheim Angels, allowing a single amid three fly ball outs.

[50][51] He returned to Shea Stadium for the final game on September 28, 2008, for the closing ceremonies with ex-teammates Edgardo Alfonzo, John Franco, Todd Zeile and Mike Piazza.

[52] Ventura's first year of eligibility for the Baseball Hall of Fame was in 2010, when he received just 1.3% of the votes, failing to reach the 5.0% threshold to stay on the ballot.

[55] In January 2020, Ventura returned to Oklahoma State to complete his degree and serve as a student assistant coach for the baseball team.

[57] In June 2011, Ventura joined the White Sox organization as special advisor to director of player development Buddy Bell.