Editing Little Orphan Annie (section)

===1929 to World War II===
Gray was little affected by the [[stock market crash]] of 1929. The strip was more popular than ever and brought him a good income, which was only enhanced when the strip became the basis for a radio program in 1930 and two films in 1932 and 1938. Unsurprisingly, Gray was mocked by some for his strip's lecturing to the poor on hard work, initiative, and motivation, while still enjoying his successful lifestyle.{{Citation needed|reason=See Talk's Subjective|date=May 2022}}

Starting January 4, 1931, Gray added a [[topper (comic strip)|topper strip]] to the ''Little Orphan Annie'' Sunday page called ''Private Life Of...'' The strip chose a common object each week like potatoes, hats and baseballs, and told their "stories". That idea ran for two years, ending on Christmas Day, 1932. A new three-panel gag strip about an elderly lady, ''Maw Green'', began on January 1, 1933, and ran along the bottom of the Sunday page until 1973.<ref>{{cite book |last1=Holtz |first1=Allan |title=American Newspaper Comics: An Encyclopedic Reference Guide |date=2012 |publisher=The University of Michigan Press |location=Ann Arbor |isbn=9780472117567 |pages=256 & 321}}</ref>

In 1935, Punjab, a gigantic, sword-wielding, beturbaned Indian, was introduced to the strip and became one of its iconic characters. Whereas Annie's adventures up to the point of Punjab's appearance were realistic and believable, her adventures following his introduction touched upon the supernatural, the cosmic, and the fantastic.<ref>{{cite book |author=Gray, Harold |author2=Heer, Jeet |year=2010 |title=Punjab and Politics |work=The complete Little Orphan Annie Volume Six: Punjab the Wizard Daily and Sunday Comics 1935–1936 |publisher=IDW Publishing |pages=5–13 |isbn=978-1-60010-792-4}}</ref>

In November 1932, Franklin Delano Roosevelt was elected president and proposed his New Deal. Many, including Gray, saw this and other programs as government interference in private enterprise. Gray railed against Roosevelt and his programs. (Gray even seemingly killed Daddy Warbucks off in 1944, but following FDR's death in 1945, Gray brought back Warbucks, who said to Annie, "Somehow I feel that the climate here has changed since I went away", suggesting that Warbucks could not coexist in the world with FDR.<ref>{{Cite web |url=http://cartoonician.com/big-deals-comics-highest-profile-moments/ |title="Big Deals: Comics' Highest-Profile Moments," ''Hogan's Alley'' #7, 1999 |access-date=November 30, 2012 |archive-url=https://web.archive.org/web/20130630083743/http://cartoonician.com/big-deals-comics-highest-profile-moments/ |archive-date=June 30, 2013 |url-status=dead }}</ref>) Annie's life was complicated not only by thugs and gangsters but also by New Deal do-gooders and bureaucrats. Organized labor was feared by businessmen and Gray took the businessmen's side. Some writers and editors took issue with this strip's criticisms of FDR's New Deal and 1930s labor unionism. ''[[The New Republic]]'' described ''Annie'' as "[[Herbert Hoover|Hooverism]] in the Funnies", arguing that Gray's strip was defending utility company bosses then being investigated by the government.<ref>{{cite magazine |author=Neuberger, Richard L. |author-link=Richard L. Neuberger|title=Hooverism in the Funnies |magazine=[[The New Republic]] |date=July 11, 1934 |page=23}}</ref> The ''Herald Dispatch'' of [[Huntington, West Virginia]], stopped running ''Little Orphan Annie'', printing a front-page editorial rebuking Gray's politics.<ref>{{cite journal |author=Clendenin, James |journal=Herald Dispatch |page=1}}</ref> A subsequent ''New Republic'' editorial praised the paper's move,<ref>{{cite magazine |title=Fascism in the Funnies |magazine=The New Republic |date=September 18, 1935 |page=147}}</ref> and ''[[The Nation]]'' likewise voiced its support.<ref>{{cite magazine |title=Little Orphan Annie |magazine=The Nation |date=October 23, 1935}}</ref>

In the late 1920s, the strip had taken on a more adult and adventurous feel with Annie encountering killers, gangsters, spies, and saboteurs. It was about this time that Gray, whose politics seem to have been broadly [[conservative]] and [[Libertarianism|libertarian]] with a decided [[populism|populist]] streak, introduced some of his more controversial storylines. He would look into the darker aspects of human nature, such as greed and treachery. The gap between rich and poor was an important theme. His hostility toward [[labor union]]s was dramatized in the 1935 story "Eonite". Other targets were the [[New Deal]], [[communism]], and corrupt businessmen.<ref>{{cite web |author=Cagle, Daryl |title=The New Deal Kills Daddy Warbucks |url=http://www.cagle.com/hogan/features/big%20events/big-events.asp}}</ref>

Gray was especially critical of the justice system, which he saw as not doing enough to deal with criminals. Thus, some of his storylines featured people taking the law into their own hands. This happened as early as 1927 in an adventure named "The Haunted House". Annie is kidnapped by a gangster called Mister Mack. Warbucks rescues her and takes Mack and his gang into custody. He then contacts a local [[US Senator|Senator]] who owes him a favor. Warbucks persuades the politician to use his influence with the judge and make sure that the trial goes their way and that Mack and his men get their just deserts. Annie questions the use of such methods but concludes it is necessary to counteract criminals manipulating the justice system in their own way.{{Citation needed|date=September 2022}}

Warbucks became much more ruthless in later years. After catching yet another gang of Annie kidnappers, he announced that he "wouldn't think of troubling the police with you boys", implying that while he and Annie celebrated their reunion, the Asp and his men took the kidnappers away to be [[Lynching|lynched]]. In another Sunday strip, published during [[World War II]], a war-profiteer expresses the hope that the conflict would last another 20 years. An outraged member of the public physically assaults the man for his opinion, claiming revenge for his two sons who have already been killed in the fighting. When a passing policeman is about to intervene, Annie talks him out of it, suggesting, "It's better some times to let folks settle some questions by what you might call ''democratic'' processes."{{Citation needed|date=September 2022}}