We've had talk enough here about George McClellan becoming president but Little Mac's son was also occasionally mentioned for the job. A typical short encyclopedia sketch of his life runs as follows:
"McClellan, George Brinton, Jr. 1865-1940, American politician and educator, b. Dresden, Saxony, Germany; son of Gen. George B. McClellan. He studied law and joined (1889) Tammany Hall, becoming one of its most prominent orators. He was president of the board of aldermen of New York City (1893-94), served as a Democrat in Congress (1895-1903), and was mayor of New York (1903-9). While serving as mayor, he broke with Tammany boss Charles Murphy over patronage, thereby ending his political career. Afterward he taught at Princeton, where he was professor of economic history from 1912 to his retirement in 1931. McClellan, an authority on Venetian history, wrote Venice and Bonaparte (1931) and Modern Italy (1933). See his autobiography, The Gentleman and the Tiger (ed. by H. Syrett, 1956)."
http://www.encyclopedia.com/topic/George_Brinton_McClellan_Jr.aspx#2
Obviously, such a sketch, while accurate as far as it goes, does not give the flavor of the man, nor does the somewhat longer article in Wikipedia.
https://en.wikipedia.org/wiki/George_B._McClellan_Jr. McClellan was a conservative Democrat in the Tilden-Cleveland-Parker tradition. Under other circumstances, his conservatism might have led him into the Republican party; but the memory of his father made that inconceivable. Moreover, unlike other gentlemen-Democrats of the Northeast--and he was very much a gentleman, an expert on the history of Venice, and a connoisseur of the arts--McClellan was a member of Tammany Hall, and an admirer of its boss, Richard Croker. In 1900, while still a member of Congress, he was mentioned as a possible vice-presidential candidate. (Certainly his name helped him. By 1900 most of the former animosity to his father had disappeared, but many of Little Mac's supporters remained, and showed a willingness to transfer their loyalties to his son.) This would have been difficult to arrange, with Bryan getting the presidential nomination--but was perhaps not impossible. Bryan bore McClellan no grudge for not having supported him in 1896; indeed he even campaigned for McClellan in New York. But they still disagreed on free silver, whatever their agreements on imperialism and other issues. (McClellan accepted Bryan's offer to campaign for him, but was nervous that Bryan might mention the "money question." "Fortunately, before he spoke, he asked me what I wanted him to talk about. I suggested imperialism as a safe subject, and he discreetly stuck to that." *The Gentleman and the Tiger*, p. 280) Of course whether a Bryan-McClellan or Bryan-anyone ticket could have won in 1900 is another question. I doubt it. Still, if Bryan had just dropped what he should have seen was the dead issue of free silver--an issue which prevented many people who agreed with him on imperialism from voting for him--he might have had a better chance, as I explain at
https://groups.google.com/d/msg/soc.history.what-if/vYXa0uF9DqM/eRZQ0E3IQrMJ
In any event, Tammany chose McClellan as its candidate for mayor against the incumbent "reformer" Seth Low in 1903. When McClellan won, there were fears of a "wide open city", but in fact it is generally agreed that his first term as mayor (1903-5) was reasonably efficient and honest; Tammany's boss Charles Murphy did get many patronage appointments, but was far from being the ruler of New York, and McCelllan "dismissed some of the more obviously incompetent officials foisted on the city by Murphy and kept a fairly close check on most of the others." (*The Gentleman and the Tiger*, p. 25; introduction by Harold R. Syrett) The consensus was that, as Jacob Riis said, he was the "best organization Mayor" New York ever had. Or as the violently anti-Tammany Reverend Charles Parkhurst, the anti-vice crusader, grudgingly said, "McClellan has given the city a clean administration as far as it was possible...McClellan, no matter what some of those who associate with him may be, is a gentleman, and has the instincts of a gentleman." In 1904 he was mentioned as a possible Democratic presidential candidate. Of course in the unlikely event he would have been nominated, he would have been slaughtered by TR as Alton Parker was in OTL.
Abyway, McClellan's political troubles began when he alienated William Randolph Hearst. In 1903 the Hearst newspapers had been among the few New York City newspapers to support the Tammany Democratic Congressman against Seth Low in the mayoralty contest, but they quickly became hostile to McClellan after he took office, denouncing him as a tool of the Gas Trust. (When Louis Lang of the New York *American* asked him, "Mr. Mayor, Mr. Hearst wants to know if you have a corrupt motive in advocating the Remsen Gas Bill?" McClellan replied, "Louis, you know better than to ask me a question like that. Get out of my office and don't come back." The next day the *American* carried a huge front-page headline: MAYOR DOES NOT DENY THAT HE HAS A CORRUPT MOTIVE IN SUPPORTING THE REMSEN GAS BILL. At least that's how McClellan told the story...)
In 1905, McClellan won re-election to a full four year term, narrowly defeating Hearst (the Republican candidate Ivins finishing a poor third, but no doubt taking votes that would otherwise have gone to the conservative Democrat McClellan against Hearst). McClellan's plurality was only 3,468, which was 0.57% of the vote.
http://www.ourcampaigns.com/RaceDetail.html?RaceID=105053 (Hearst of course screamed fraud for years afterwards.) It seems that McClellan was impressed by the size of Hearst's vote as a sign of anti-machine sentiment. He may also have felt that while Tammany had given him his start in politics, the time had now come for him to establish a reputation as an independent. Furthermore, he had come to personally dislike Tammany's boss Charles Murphy (whereas he had liked and even admired Murphy's predecessor Richard Croker). Meanwhile, Murphy, whose position in Tammany was much stronger than it had been in 1903, was demanding that all the jobs in the administration go to Tammany; McClellan refused.
So there was a feud between McClellan and Tammany for the mayor's entire second administration. McClellan dismissed all Tammany office holders who would not pledge to support for him over Murphy, and there were widespread predictions that "Murphyism" was doomed. But Murphy proved invincible in the Democratic primaries. In fact, by the end of McClellan's second term, Murphy's control of the Democratic party in New York City was more absolute than ever. After McClellan left the mayoralty in 1909--having done a good job as mayor, by most accounts--he was never nominated for any office again. After a brief and unhappy career at a law firm, he became a member of the faculty of Princeton University from 1911 to 1931, with a leave of absence during World War I.
It is generally thought that McClellan's quarrel with Murphy doomed his political career. Yet one must remember that a number of politicians in that era made a name precisely by defying the party bosses who had first put them into power (the most obvious example is Woodrow Wilson and Boss Jim Smith of New Jersey). And Tammany after all did not control all of New York state. Even in New York City, Patrick H. McCarren, leader of the Brooklyn Democratic organization, broke with Murphy in 1904 and ran the Brooklyn organization as an autonomous machine until 1909. (There was a long tradition of Brooklyn Democrats being suspicious of Tammany's attempts at aggrandizement--"The Tiger shall not cross the bridge!" was a popular saying in Brooklyn.) He was outspoken in his backing of McClellan against Murphy. But McCarren died suddenly in 1909, and was replaced by a pro-Murphy Brooklyn politician, John McCooey. McClellan was later to comment: "Had McCarren lived, I should have had a better than sporting chance of landing the governorship, which was the goal I set myself. In fact, I think that I should have won, despite Murphy, which would have put me in the running for the presidency in 1912." (*The Gentleman and the Tiger*, p. 285)
So let's take as our POD that McCarren doesn't die in 1909, and that he and other anti-Murphy Democrats do get McClellan the Democratic nomination for governor in 1910. There is then a likelihood that Murphy's forces will "knife" McClellan in the general election, and that the Republican candidate for governor, Henry Stimson, will then win. This offers the interesting prospect of President Stimson (in 1916--or maybe even in 1912 in the unlikely event that TR and Taft realize their strife is mutually suicidal and agree to support Governor Stimson as a compromise candidate) which I have discussed elsewhere.
https://www.alternatehistory.com/forum/threads/president-henry-l-stimson.390669/ However, let's say that McClellan wins (which, despite any sabotage by Murphy, is plausible; 1910 was a Democratic year, and anyway Tammany opposition would gain as well as lose votes for McClellan). Can he become president in 1912? Doubtful, but I wouldn't totally rule it out. It is true that he was a conservative, and that the Democratic party was not in a conservative mood in 1912. But Wilson had once been a conservative Cleveland Democrat, and made himself acceptable to progressives; maybe McClellan could do the same. OTOH, McClellan's conservatism seems much more deep-dyed than Wilson's. Perhaps the most he could hope for would be the vice-presidency (and then only if Champ Clark or someone from farther away form New York than New Jersey won the top post) which might then lead to the presidency in the event of assassination or ill-health of the president...
If he *had* somehow become president, it is interesting to speculate what his foreign policy would be like. The reason is that in OTL after his trip to Europe in 1915 he wrote a series of newspaper articles republished in book form as *The Heel of War*
https://archive.org/stream/heelofwar00mccl#page/n7/mode/2up which was widely denounced as pro-German. He asserted that life in Belgium under the Germans was "not abnormal in any way," that "the accounts of serious damage to the city [of Louvain] were greatly exaggerated" that conditions in Germany were "perfectly normal" and that in France "there was no real hatred for Germany except among [the] American colony and a small section of unrepresentative French." When America entered the war, however, he volunteered for military service, though fifty-one years old. In his autobiography, McClellan (who had campaigned for Wilson in 1916) complained that "the logical and proper moment to have given Bernstorff his papers was after the sinking of the *Lusitiania.* Wilson allowed that opportunity to pass and broke off relations in February [1917] with much less forcible reasons." (*The Gentleman and the Tiger*, p. 347) So on the one hand McClellan complains about "war hysteria" and "Allied propaganda" leading to an unfavorable reception of his book; on the other, he suggests Wilson should have broken off relations with Germany *sooner.*
A few words about McClellan's books other than *The Gentleman and the Tiger* (the only book of his I've read; the observations about the others are from that book, including the editor's introduction) and *The Heel of War*: *The Oligarchy of Venice* (1904)
https://archive.org/stream/oligarchyofvenic00mccluoft#page/n5/mode/2up as McClellan said, made no claims to originality, but, as he remarks, some kindly reviewers "expressed surprise that a Tammany mayor was capable of writing the English language." *Venice and Bonaparte* (1931) OTOH was based on research in the Venetian archives, and was McClellan's best received work among historians. McClellan criticized the Venetian oligarchy--as in *The Oligarchy of Venice* he drew parallels with American political machines--and concluded that Napoleon's policy toward the city was justified. Finally, *Modern Italy,* (1933),
https://archive.org/stream/modernitalyashor000926mbp#page/n5/mode/2up a superficial survey (McClellan himself said it made "no claims to scholarship", and it neglected economic, social, and intellectual history almost entirely) of Italian history from the Congress of Vienna to the rise of Fascism concludes with a panegyric to Mussolini (according to McClellan, Italians as "Latins" had neither the desire nor the aptitude for democracy):
"He has evolved a new theory of government and made a new state, both peculiarly adapted to the genius of the Italian people. He has ruled that state with an eye single to its best interests. He found it suffering from the loss of its self-esteem due to the settlement of the World War, and has made it one of the great powers of Europe. He found it distracted with internal disorder, with ill feeling against its former allies, and with almost ruined finances. He has restored peace at home and good-will abroad, and the finances of his country.
"With infinite patience, a patience seldom met anywhere, but most rarely in Italy, he has taught his people the habit of fascismo and by doing so has broken down regionalism. For the first time there is a united country of men and women who, forgetting that they come from this or that province, under the inspiration of the duce remember only that they are the children of one great nation.
"He has taught his people to think nationally and has after many years fulfilled the hope of d'Azeglio, for as Cavour made Italy, Mussolini has made Italians."
https://archive.org/stream/modernitalyashor000926mbp#page/n293/mode/2up/
Granted that such sentiments were not uncommon in the US at the time, this is laying it on a little thick. McClellan boasted in his autobiography (*The Gentleman and the Tiger*, p. 369):
"A copy of my book [was sent] to Mussolini, who...stated that he found it interesting, fair, and 'most objective' and proceeded to make me a Commander of the Order of the Crown of Italy, to be followed on my seventy-second birthday by promotion to the rank of 'Grand Officer' of the same order."
All in all, I can't say that McClellan would have been a great president, or that there was much chance of his ever becoming president. Still, *The Gentleman and the Tiger* is worth reading, if only for some of its anecdotes. My favorite (I am pretty sure it's apocryphal...) is of Theodore Roosevelt wiring Mrs. Grover Cleveland "Am greatly distressed to hear of your husband's death. Hope funeral will not be on Friday as I want to go to the Harvard-Yale boat race that day"...
(Incidentally, his being born in Dresden almost certainly would not stand in his way. The consensus among lawyers, at least at that time, was that someone born to American citizen parents temporarily living abroad was a "natural-born citizen" within the meaning of the Constitution. As the Republican and very anti-McClelllan *New York Tribune* remarked, "If the question of his eligibility were all that stood between McClellan and the presidency he would have no cause to worry.")