That’s Don Zimmer, who managed the Cubs from 1988-91, being interviewed by a Cardinals broadcaster (more on him later) — you can see the Cardinals logo on the mic flag.
If this were the entire photo I wouldn’t be able to tell you anything about the date, all I could tell you was that it was taken at Wrigley Field. Getty Images says it was taken in “the late 1980s” and, well, that’s pretty obvious from Zimmer being interviewed. (Yes, Zimmer was also a Cubs coach from 1984-86, but that position wouldn’t likely have gotten him interviewed by a Cardinals broadcaster.)
But it’s not the entire photo. Here’s the full image:
Now we know it was taken on a sunny day in summertime, ivy full on the bleacher wall, at about 11:40 a.m.
Those team names on the scoreboard are pretty blurry, but we already know the Cubs are playing the Cardinals. After a lot of squinting, I got the rest of them.
NL side: ATLANTA/CINCINNATI, PITTSBURGH/NEW YORK, SAN FRANCISCO/HOUSTON, LOS ANGELES/SAN DIEGO, PHILADELPHIA/MONTREAL, ST. LOUIS/CUBS
AL side: MINNESOTA/KANSAS CITY, TORONTO/CLEVELAND, BOSTON/CALIFORNIA, BALTIMORE/TEXAS, NEW YORK/OAKLAND, CHICAGO/DETROIT
With no night games listed, this has to be a Sunday. There is just one Sunday during Zimmer’s tenure as manager that matches the matchups shown: Sunday, September 10, 1989. The Cubs had just defeated the Cardinals in a thrilling extra-inning game the day before to avoid falling out of first place, so having Zimmer appear on a Cardinals broadcast before the Sunday game would have made sense. The shadows on the scoreboard, too, would match a mid-September day around noonish. If the photo had shown the right-field bleachers about two sections to the right, I probably could have picked myself out of the crowd.
I didn’t recognize the Cardinals broadcaster so I enlisted Josey Curtis and her staff at Viva el Birdos for an ID. They say it’s a “clean-shaven Al Hrabosky” and I concur with that; “The Mad Hungarian,” as Hrabosky was known, generally had generous facial hair but those were his early days in broadcasting (he began as a Cardinals announcer in 1985) and it could be that the TV channel wanted a cleaner look at the time. Many thanks to Josey and the VEB staff for their help.
So, this interview took place about an hour and a half before the Cubs/Cardinals game Sunday, September 10, 1989. The Cubs won the game that day 4-1, the second of what eventually became a six-game winning streak that put them 5½ games in first place and put them on their way to clinching the division in Montreal September 26.