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The "Kerwin" mentioned was Milwaukee County District Attorney James J. Kerwin, who had declared a high-profile war on gambling (particularly slot machines and bingo) the year before.
That's a lot to wrap up into a single panel.
The cartoonist, Lou Grant, has a great story all his own. A native of Los Angeles, he joined the Sentinel as a sports cartoonist in 1944, after a three-year hitch in the Army.
Grant was soon known for his whimsical figures, seen here on this page-width illustration from April 25, 1945, marking the Brewers' home opener:
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Here we see his impression of outfielder Hal Peck's career. Peck, known as Bill Veeck's "good luck charm", had already served one stint in the majors with the Brooklyn Dodgers and was being shopped around.
Of course, Grant covered more than just baseball. This was his impression of the horse races at Wisconsin State Fair Park:
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Grant's influence spread beyond the national press. According to the Los Angeles Times, the writers of "The Mary Tyler Moore Show" named their grumpy journalist/news director, played by Ed Asner, after the cartoonist.
Lou Grant the character would later be spun off into his own eponymous newspaper-set show, and the cartoonist's name would remain famous, in syndication, long after his death in 2001.
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