The Cubs raised their 1907 World Championship flag at West Side Grounds on May 21, 1908—the flag “orange letters on a blue field” according to The Chicago Inter Ocean; The Chicago Tribune described it as “royal purple and gold.”
I.E. Sanborn of The Tribune said “There were music, flowers and enthusiasm in bunches” at the ceremony, until:
“(T)he world’s champions spoiled it all by an exhibition which made the handsome creation of royal purple and gold hang its graceful folds in shame.”
The Boston Doves beat the Cubs 11-3.

The Box Score
The Pittsburgh Press said the game was part of a trend:
“Undesirable happenings have attended the raising of the world’s pennants. The flag won by the Chicago Cubs from the Detroit Tigers was unfurled in Chicago Thursday.
“The result was saddening to the superstitious ones. The Cubs were walloped good and plenty by the Boston Nationals. It being necessary for the Cubs to sacrifice three pitchers in the carnage.”
The paper said the was a “Hoodoo connected” to the raising of championship flags.
“In the spring of 1906 the New York Giants floated the big flag in the Polo Grounds before a large crowd.”
The New York Times said of the June 12 ceremony:
“With admiring thousands following at the wheels, the New York Giants, the champion baseball team of the world—at least last year—paraded down Broadway in automobiles yesterday morning. Before and behind them marched a small army of boys baseball clubs…Mounted police clattered ahead of the procession to make clear the way. It was a great triumph for the Giants.”
The Times said the flag was “of blue bunting, trimmed with gold, is 45 feet long and 20 feet wide, and contains the inscription New York Baseball Club, 1906 Champions of the World.”
Then, “the Giants, whose fielding was extremely poor, while their batting was of an inferior order, only three men out of ten being credited with safe hits.”
They lost to the Reds 6 to 1.

The Box Score
Then, said The Press, there was May 14, 1907, “the notable flag raising on the Chicago South Side Grounds.”
I. E. Sanborn described that flag raising:
“Just as 15,000 throats were swelling with the first notes of the grand paean which was to have marked the climax of Chicago’s biggest baseball fete, just as the silken banner, emblematic of the highest honors of the diamond, had shaken out its folds over the White Sox park and started its upward climb in response to the tugs of the heroes of the day, Comiskey’s veteran flagstaff swayed, trembled in every fiber, then broke squarely off in the middle and toppled back to the earth which reared it.
“The tall spire of pine which had withstood for seven years the fiercest gales, which had flaunted defiantly three American League pennants and a dozen American flags until they were whipped to ribbons by the wind, proved unequal to the task of lifting a world’s championship banner.”

The scene just before the pole broke
The game itself lasted just four batters when “a heavy shower” ended the game with Washington “and drenched thoroughly the gay raiment of the great crowd, only a part of which could find shelter under the protected stands.”
The Press noted that not only did the Giants and White Sox have bad luck on flag-raising day, both “failed to repeat as winners” and said:
“The big flag may prove a hoodoo.”