Getty Images says:
Mark Grace #17 of the Chicago Cubs in action against the Florida Marlins during an Major League Baseball game circa 1993 at Wrigley Field in Chicago, Illinois.
The baserunner is Benito Santiago of the Marlins. He wore that unusual two-digit “09” for the Marlins in 1993 and 1994.
Given the caption, I started with the 1993 games. There were just two in which Santiago played against the Cubs at Wrigley Field that year. In a September 1993 game, Santiago pinch-hit a single to left, so that can’t be what we are looking at here. (And besides, it was overcast that day, per the boxscore.)
That leaves just one possible game, and that was played Tuesday, June 15, 1993. It was sunny and 64 degrees that day, explaining both the shirtsleeve crowd and Grace wearing a long-sleeve shirt.
This play happened in the ninth inning. With one out and the Cubs leading 3-0, Santiago hit a ground ball to short, but Cubs shortstop Rey Sanchez made a throwing error and Santiago reached base. You can see the Marlins’ first-base coach pointing to first base, indicating to Santiago that he should stay there.
Randy Myers got the next hitter to hit into a game-ending double play. Cubs connection! That hitter was future Cubs manager Rick Renteria.
Now, to the question posed above: Why was Benito Santiago wearing “09” instead of just plain “9”?
Believe it or not, this is the reason:
Benito Santiago never wore 0 or 00, but he did wear 09, because he didn’t like how his single-digit 9 was being bisected by the vertical strap on his chest protector.
So it was basically for... style points.
Santiago, who had worn just plain “9” for the Padres from 1987-91, switched to “09” halfway through 1991, wore it through 1992 with the Padres and in 1993-94 with the Marlins. When he signed with the Reds for the 1995 season, he switched to 18 and kept that through 1998 with the Blue Jays.
It was a pretty forgettable year, but Santiago was a Cub in 1999 and switched back to 9 — just plain 9, no leading zero. He hit .249/.313/.377 with seven home runs in 109 games and departed via free agency after the season, returning to the Reds. He followed that with three years in San Francisco, one in Kansas City and one in Pittsburgh to complete a 20-year career.
But he never wore “09” after 1994.