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- Values Dissonance: Chesterton's racial and national attitudes were actually very moderate for the early twentieth century, but some (particularly in regards to the Jews) will often strike a sour note for modern readers in the midst of his most enjoyable works. This is mainly accidental, being connected less with racial theories (which he despised) than with a distrust of internationalism and big combines in general. His religious views, on the other hand, were entirely conscious, and will strike the reader as either refreshingly forthright or offensively aggressive. His opposition to progressivism, including essentially reactionary approaches to socialist welfare programs (such as government-mandated health insurance), science, and women's suffrage may irritate modern progressives, while his radical disdain for individualism, Realpolitik, nationalist expansionism, and capitalism may provoke modern conservatives.
- Chesterton actually defended the Jews against the growing anti-Semitism in the West; in fact, he was one of the few people who thought the Nazis were bad enough to go to war against before WWII. Some of his reputation as an anti-Semite comes from confusion with his cousin, A K Chesterton, who was a fascist political activist and one of the most extreme Nazi-style conspiratorial anti-Semites among the British inter-war far right.
- GKC's anti-Semitism was, to an extent, exaggerated as a result of his associations, such as with his brother Cecil Chesterton and with his close friend Hilaire Belloc, both of whom were more aggressive in their (verbal) attacks on Jews than GKC was. (In Cecil's case this was mostly due to his anti-capitalism and to a certain anti-Disraelism prevalent in adherents of the Liberal Party (and detectable in GKC himself), in Belloc's case due to his French-style nationalism.) In all of these men there was a genuine element of anti-Judaism (in a religious sense) and anti-Hebraism (in a nationalist sense), which must, however, be distinguished from the racial anti-Semitism prevalent at the time. There is not one of them who would have not been sickened and horrified by the National Socialist atrocities in Germany (the general tendency of which they foresaw, but the scope of which was unimaginable to nearly everyone at the time); there can be no doubt that all of them, if they had been confronted with the enormity of the Shoah, would have utterly repudiated Nazi anti-Semitism. GKC himself was a convinced Zionist; and he believed that most of what was "wrong" with "the Jews" was a result of their being denied the opportunity to lead their own independent national life. Nevertheless, it cannot honestly be denied that GKC and his circle were widely regarded in his own time as vehemently anti-Semitic, for whatever reason, and the charge, though it may be and in fact is greatly mitigated by a number of circumstances, particularly in GKC himself, remains at least somewhat valid.
- One True Pairing: Chesterton once wrote an essay regarding Don Juan of Austria (no relation to the famous lover of the same name) and Mary Queen of Scots. His focus was not particularly on the "bohemian" details of their romance but on the fittingness of such a pairing and the historical-political implications across time.