Derek Jeter Says Roy Halladay Was the Toughest Pitcher He Faced

Derek Jeter produced one of the most prolific careers during his time in Major league Baseball. The Yankees legend reached 3,000 hits, finishing sixth in MLB history in career hits and first among shortstops. Even more, the five-time World Series champion was named to the Baseball Hall of Fame in his first year of eligibility.

On his way to achieving some of MLB’s greatest achievements, the 14-time All-Star faced some great pitchers in the process. Jeter joined the Talkin’ Baseball podcast to share the toughest pitcher he faced during days on the diamond.

Jeter said former Blue Jays and Phillies pitcher Roy Halladay would get the best of him. “I could not figure him out,” Jeter said.

Halladay, known for his durability, was an eight-time All-Star and two-time Cy Young award winner who led the league in complete games seven times, the most by any pitcher who started their career after 1945.

In 104 appearances at bat against Halladay, Jeter posted a .234 average and .571 OPS. Halladay, who was inducted into 2019 Hall of Fame, struck out Jeter 24 times in his career, which was more than any other pitcher.

While Halladay was the toughest, Jeter said that the best pitcher he ever faced was eight-time All-Star and three-time Cy Young award winner Pedro Martínez. While Martínez played for five different MLB teams—Dodgers, Expos, Red Sox, Mets and Phillies—he helped Boston win its first World Series in ’86 years in 2004.

Jeter is one of the all-time greats in MLB, but even he had his difficult matchups.