The cartoonist in question, who created the popular image of the Brooklyn Bum, was Willard Mullin, also of the old New York World Telegram, and perhaps the finest sports cartoonist of them all. I know otherwise, of course, but a piece of me prefers to think that sports cartooning became a dying art in American newspapers because, when Willard Mullin finally retired, newspaper editors realised sadly enough that they could never improve on perfection.
Here is one of Mr. Mullin's typical illustrations, which was actually the cover of the 1951 Brooklyn Dodgers' yearbook:
Here is a classic Mullin, the cover of the 1964 New York Mets yearbook. (Mullin's cartoons during the Mets' early seasons were just as classic as in the days of the Dodger-Giant-Yankee rivalries, and in fact Mullin did Met yearbook covers until the early 1970s.):
Click on either cartoon to see a charming site devoted to the man and his art.
(The allusion to "Mrs. Dressen," by the way, refers to Dodger manager Charley Dressen's wife writing O'Malley a very testy letter in which she made even more vociferous a demand for a multi-year contract than her husband had done. When Dressen insisted on the three-year deal only by saying "My wife and I got to have security," O'Malley - who held strictly to single-year contracts, after a few instances of the Dodgers canning managers before multiyear deals expired, meaning they still had to pay those deals - released Dressen, who went on to manage the minor-league Oakland Oaks, the major league Washington "First in war, first in peace, and last in the American League" Senators, and Detroit Tigers, the latter a job he held until his death in 1966.)