From the Pages of Vine Line: Remembering 1998 – Windy City walk-off

Fifteen years ago, the 1998 Cubs squad became the must-see event of the summer, as viewers around the country tuned in to WGN to see Sammy Sosa, Kerry Wood and the cardiac Cubs stage one of the most dramatic seasons in Chicago baseball history. Day after day, it seemed like the team was in a dogfight, and every win turned out to be vital, as the Cubs need an extra, 163rd contest to finalize their postseason push and give Chicago fans their first taste of meaningful October baseball in nearly a decade.

To commemorate all the ups and downs, Vine Line celebrates our 10 greatest moments from that historic 1998 campaign in the October issue of the magazine. Today marks the fourth part of the 10-part series, which we’ll post here on the blog in the coming days.


(Photo by Stephen Green)

6/5/98 – Crosstown Classic walk-off

When most people think of Brant Brown in 1998, they remember the dropped fly ball with two outs in the bottom of the ninth of Game 159 that nearly cost the Cubs their playoff dreams. What many forget is that three months earlier, Brown played the hero in the first-ever regular season Crosstown Classic matchup at Wrigley Field.

In the June 5 affair, the Cubs were trailing 2-0 after the first inning, but bounced back to take a three-run lead by the fifth, thanks to a third-inning three-run double from Henry Rodriguez and a fifth-inning two-run bomb from Sosa. After the Sox tied things up in the top of the sixth, the game became a pitchers’ duel with both bullpens holding the opposition scoreless until the 12th.

Then Brown stepped into the box in the bottom of the frame and took a 1-0 pitch from Tony Castillo over the right-field fence for a dramatic ending to the crosstown showdown.

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