This entry on the list is another that comes under the category of "meaningless, but memorable".
The 1987 Cubs were a pretty bad team -- after being in first place in May and staying close into early June, they quickly fell into fifth place and finished last in a mind-numbing drop-by-drop fall. There weren't any long losing streaks -- from July 1 to the end of the year the longest one was four -- but they couldn't get any winning streaks together, either; the longest winning streak of the entire year was five, done only once, in May. The boring Gene Michael was finally dumped as manager in early September, replaced by the even more boring Frank Lucchesi. The team did enter September over .500, but went 10-21 after September 1.
And so, about the only things worth watching that year were the pitching of Rick Sutcliffe, who won 18 games and should have won the Cy Young Award, and the hitting of Andre Dawson, who was named league MVP.
This MVP award has been controversial because the Cubs finished last and Dawson's peripheral stats -- apart from leading the league in HR, RBI and TB -- weren't that great (he scored only 90 runs despite hitting 49 HR). It wasn't even Dawson's best year -- his 1983 season with Montreal was quite a bit better.
But with the attitude he brought to the team, his solid defense in RF, and the HR he hit, he quickly became a fan favorite. Dawson himself said, of that season:
And on September 27, the last home game, a sunny Sunday, all wondered whether Dawson would give the fans one last memory. In his first four at-bats he had struck out, singled, singled and struck out. And then, he came up in the bottom of the 8th, with two out and the Cubs leading the Cardinals 6-3. Clearly, this would be his final appearance before the home crowd. It's easy to say now, 20+ years later, that we all knew he was going to hit one, but that was the feeling all of us in the ballpark had that day. Andre didn't disappoint. He ran the count to 3-1 against St. Louis reliever Bill Dawley, and then hit a ball far onto Waveland Avenue.
Meaningless? Sure. Memorable? You bet. The Cubs won the game 7-3, but Andre Dawson gave us enough memories to last a lifetime. He hit two HR on the Cubs' final road trip (in looking this up, I discovered that Lucchesi had batted Dawson second in the final two games, at Montreal, likely to try to get him some more AB), giving him 49 for the season, at the time, second-most in Cub history for a single season.