The Chicago Cubs broadcasting booth has been graced with plenty of talented people. Jack Brickhouse, Vince Lloyd, Steve Stone, Lou Boudreau, Ron Santo, Pat Hughes, Bob Brenly, and even Len Kasper. However, none of these talented men were ever embraced by the fan base, and the nation, quite like Harry Caray.

A longtime baseball broadcaster, Caray joined the Cubs WGN-TV broadcast in 1982 after spending time with the Cardinals and White Sox (everyone remembers disco demolition night at Comiskey, right?). The timing was impeccable for Caray, as the Cubs would go on to win the pennant in 1984 along with WGN being one of the first TV networks to allow their games to broadcast nation-wide for free. So America was treated to Harry and his wide-frame, prescribed may I note, glasses and his interest in-game antics that included his exuberant catch phrase “Holy Cow” and reading players names backwards.

“Now, you tell me, if I have a day off during the baseball season, where do you think I`ll spend it? The ballpark. I still love it. Always have, always will.”

He was a baseball fan first. Broadcaster second. The fans loved him for it, especially Cubs fans, who hold a special attachment to Caray and his favoritism towards the North-Siders and certain alcoholic beverages (he loved himself a nice, cold Budweiser). But as dearly beloved as he was by the Cub faithful, Caray might have loved the Cubs and baseball just a little bit more. There’s not too many people who could have a stroke and have their first reaction be to get back to Wrigley Field and call more baseball games. This is his reaction to the end of the 1991 season, the Cubs finished 77-83 4th in the East, and weren’t going to the playoffs.

He loved Cubs fans. And they loved him back.

“This has been the remarkable thing about the fans in Chicago, they keep drawing an average of a million-three a year, and, when the season’s over and they’ve won their usual seventy-one games, you feel that those fans deserve a medal.”

When Caray passed away in 1998, the Cubs wore these patches in remembrance of the legendary broadcaster. It also happened to be the year Sammy Sosa hit 66 home runs. Since installing the two massive jumbo-trons at Wrigley Field, the Cubs routinely play Caray’s rendition of “Take me out to the ball game.” A song he said he liked singing because,  “It’s the only song I know the words too, ” and he probably wasn’t kidding.

But his love for baseball and the Cubs can still be felt in Wrigleyville, even after almost 20 years since the kooky broadcaster passed.

Will Ferrell still does his impersonation of the Cubs great, fans show up to games wearing the giant, wide-framed glasses he made a Chicago icon, and people still love to shout “Holy Cow” whenever one of the Cubs sends a ball into the stands.

Urban Gameday, a local apparel company in Chicago, has helped keep Harry’s memory alive by creating a special, “Win It For Harry” tee. This tee has been circulating Wrigleyville since Theo arrived, and will continue to be purchased around the town until the Cubs pull it off.

Remember Susannah Collins? Fan-favorite reporter in Chicago whose time was cut short? She supports Harry.


So does local fan Josh Epstein, a recent winner of a FREE “Win It For Harry” tee from Urban Gameday. (they hand out a free shirt every Friday on Twitter.)

“Harry represents what Cubs fans should be, die-hard and enjoying every moment while sticking with the team not matter what” Epstein said.

It’s fans like Caray that make the Cubs seem deserving of a championship. Other teams have to earn it, as they will, but no other team has seemly suffered as long as the Chicago Cubs.

That is why the Cubs have so much pressure to win it all this year, in the name of devoted fans like Caray. It is truly remarkable to think nobody currently living has seen a Cubs’ World Series win. They haven’t even appeared in one since 1945. Rany Jazayerli of The Ringer, puts it like this.

“Unfathomable though it may be, it is also undeniable: The Cubs have pissed away a sizable competitive advantage for 108 years, which is why their pursuit of a championship is the greatest ongoing adventure in American sports.”

With the team’s overwhelming success this season, this is unquestionably the greatest chance the Cubs have had at breaking professional sports’ longest championship drought.

The Cubs have scored 159 more runs than they have allowed this season. If All-Star voting ended today, their entire infield would be starters. Their Ace, Jake Arrieta, won the Cy Young award last season and statistically isn’t even the best pitcher in the rotation right now. This team looks to be the one that might finally do it, and Wrigleyville should be making it a point to pay tribute to previous fans who have literally died waiting for their team to celebrate a World Series trophy.

So, this September, when the Cubs are playing in their first playoff game of 2016, and the 7th inning stretch is about to commence. Grab a nice, cold Budweiser, belt-out a “Holy Cow”, and sing it for Harry.

Hopefully a World Series championship will follow.