The pitcher that Tony Gwynn could not hit

Frank DiPino

Frank DiPino spent more than a decade in the big leagues, and he pitched in more than 500 games. He was a hard-throwing lefty and useful out of the bullpen, his best seasons coming with the Astros, Cubs, and Cardinals. He was never a LOOGY, but he was a situational lefty, which is what they called the wrong-handed middle relievers in those days. One year in Houston, DiPino saved 20 games.

But Frank may have been in the majors for one reason and one only: to get out one of the best hitters in history.

Tony Gwynn won eight batting titles and hit .300 in 19 of his 20 major league seasons. He had a swing that made pitchers cry themselves to sleep. He had a special knack for hitting screaming line drives between third and shortstop. Gwynn hit .429 against the best pitcher of his generation, who might have been the best pitcher of all-time. .429!

But Tony Gwynn couldn’t hit Frank DiPino.

Who the hell is Frank DiPino? Sounds like a character from The Sopranos.

You are forgiven for not knowing who DiPino is. But if Gwynn were here (the Hall of Famer died way too early at the age of 54 six years ago), he could tell you all about the little left-handed pitcher.

DiPino faced Gwynn 23 times. He walked Gwynn once, and Tony got a sacrifice fly and a sacrifice bunt once. In the other 20 plate appearances, DiPino owned Gwynn to the tune of 1-for-20. That’s a .050 batting average, which is only one-fourth of the Mendoza Line. That’s 288 points below Gwynn’s career batting average. It’s the type of record that gets a hitter sent to Amarillo, which is where Gwynn started his pro career. Tony batted .462 in Amarillo, and let’s face it, Gwynn hit everywhere he played, and in almost every situation.

Gwynn batted .343 in home games. He hit .334 on the road. He batted .342 before the All-Star break, and .334 after. This is what he hit by month, starting in March and ending in October: .339, .346, .333, .344, .325, .348, .335, and .332. The San Diego outfielder hit .375 when swinging at the first pitch, and he batted .351 with a full count. With two strikes on him, he batted .302, which is absurd. Ridiculous, and unheard of. Add your adjective here.

Gwynn hit .344 in the 1990s and won his last four batting crowns. He hit .324 in the 2000s when he was past his 40th birthday. And in the 1980s he batted .332 and won the first four of his batting titles.

Against Nolan Ryan, Gwynn hit .302, and he famously never struck out against Maddux in 91 at-bats. He batted .462 with 12 extra-base hits off John Smoltz. Against Maddux, Tom Glavine, and Smoltz, the three great Braves’ pitchers, Gwynn batted .393 with only three strikeouts in more than 260 plate appearances. Unbelievable.

But against Frank DiPino, the crafty little lefty who stood all of 5’10 and weighed about 170 pounds, Tony Gwynn was 1-for-20.

Maybe you think it was because DiPino was left-handed. But the left-handed hitting Gwynn batted .325 against southpaws in his career. Lefties didn’t typically bother him, unless you were DiPino.

The first time a manager summoned DiPino specifically to face Gywnn was in 1988 when the lefty was with the Cubs. DiPino got Tony to hit a soft fly ball to left field. Two nights later, DiPino came in with a runner on base and two outs in the seventh inning to face Gwynn, getting another fly out to end the frame. By this time, Frank was known to be a nuisance to the greatest hitter in the game. Later that season he struck out Gwynn in extra innings and earned a victory.

It didn’t matter what uniform DiPino wore: Gwynn was 0-for-5 against him when he was in Houston; 1-for-8 when Frank was a Cub; and 0-for-7 when DiPino was employed by the Cardinals.

How do you explain when an otherwise unspectacular pitcher shuts down a great hitter?

Sometimes in baseball, you just can’t explain it.

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