The funeral of famed Chicago gangster Dion "Deany" O'Banion in 1926 was attended by some ten thousand mourners. O'Banion, a flower "entrepreneur" whose shop, at the corner of State and Superior Streets, was a front for his bootlegging and hijacking operations, was the recipient of several beautiful funeral wreaths -- the most extravagant of which by far was a $1,000 gift from rival gangster Al Capone. Despite Capone's generosity, however, the incident prompted a vicious gang war; Capone himself, after all, had ordered O'Banion's killing.
[Capone's listing in the 1920 Chicago telephone directory? "Second-hand furniture dealer, 2220 S. Wabash Ave." Capone was convicted and imprisoned for tax evasion in 1931.]