"Why... WHY did you succumb to this problem that we foresaw but did nothing to prevent!?"

To be fair, the two party system was a natural evolution within the government structure created by the Founding Fathers. Whether or not any individual president was a fan or not would never have prevented it.

Lotta people trash talking Washington but I don’t think ever actually read anything about him or read anything of substance he’s written.

But as it is easy to foresee that, from different causes and from different quarters, much pains will be taken, many artifices employed to weaken in your minds the conviction of this truth; as this is the point in your political fortress against which the batteries of internal and external enemies will be most constantly and actively (though often covertly and insidiously) directed, it is of infinite moment that you should properly estimate the immense value of your national union to your collective and individual happiness; that you should cherish a cordial, habitual, and immovable attachment to it; accustoming yourselves to think and speak of it as of the palladium of your political safety and prosperity; watching for its preservation with jealous anxiety; discountenancing whatever may suggest even a suspicion that it can in any event be abandoned; and indignantly frowning upon the first dawning of every attempt to alienate any portion of our country from the rest, or to enfeeble the sacred ties which now link together the various parts.

….

In contemplating the causes which may disturb our Union, it occurs as matter of serious concern that any ground should have been furnished for characterizing parties by geographical discriminations, Northern and Southern, Atlantic and Western; whence designing men may endeavor to excite a belief that there is a real difference of local interests and views. One of the expedients of party to acquire influence within particular districts is to misrepresent the opinions and aims of other districts. You cannot shield yourselves too much against the jealousies and heartburnings which spring from these misrepresentations; they tend to render alien to each other those who ought to be bound together by fraternal affection.

….

However combinations or associations of the above description may now and then answer popular ends, they are likely, in the course of time and things, to become potent engines, by which cunning, ambitious, and unprincipled men will be enabled to subvert the power of the people and to usurp for themselves the reins of government, destroying afterwards the very engines which have lifted them to unjust dominion.

And probably the most relatable to today:

I have already intimated to you the danger of parties in the State, with particular reference to the founding of them on geographical discriminations. Let me now take a more comprehensive view, and warn you in the most solemn manner against the baneful effects of the spirit of party generally. 

This spirit, unfortunately, is inseparable from our nature, having its root in the strongest passions of the human mind. It exists under different shapes in all governments, more or less stifled, controlled, or repressed; but, in those of the popular form, it is seen in its greatest rankness, and is truly their worst enemy. 

The alternate domination of one faction over another, sharpened by the spirit of revenge, natural to party dissension, which in different ages and countries has perpetrated the most horrid enormities, is itself a frightful despotism. But this leads at length to a more formal and permanent despotism. The disorders and miseries which result gradually incline the minds of men to seek security and repose in the absolute power of an individual; and sooner or later the chief of some prevailing faction, more able or more fortunate than his competitors, turns this disposition to the purposes of his own elevation, on the ruins of public liberty. 

Without looking forward to an extremity of this kind (which nevertheless ought not to be entirely out of sight), the common and continual mischiefs of the spirit of party are sufficient to make it the interest and duty of a wise people to discourage and restrain it. 

It serves always to distract the public councils and enfeeble the public administration. It agitates the community with ill-founded jealousies and false alarms, kindles the animosity of one part against another, foments occasionally riot and insurrection. It opens the door to foreign influence and corruption, which finds a facilitated access to the government itself through the channels of party passions. Thus the policy and the will of one country are subjected to the policy and will of another.

Y’all should read his farewell speech. It’s like he was a time traveler, and why this meme says “I told you so”.

Political parties in general. The problems specific to a two-party systems weren't understood yet. Being that the United States was figuring out how a modern democracy should work as it went, that's not surprising.

This was already seen well before he was even done being president. By 1800 it's obvious the 2 party dysfunction was well in motion.

I think that podcast American Elections: Wicked Game tells some of that story pretty well of the early political fighting and party divisions.

How? He looked at history, and every two-party system that came before.

Many countries without the two party system have the same problems though

Don’t you say that about my FOunDinG DaDdy!!

This where entrenched lobbying, corruption and bribery has taken us. Corporations are NOT "people."

In such times, the lessons of history seemed less distant.

If somebody is to make a 3rd or 4th party, how much and how long will it take for them to be able to compete with the other 2?

My greatest wish for this election season is that everyone would just vote for Taylor Swift. I personally don’t care much for her music, but she has a lot of popularity right now and I think she would do a better job than anyone else currently running. The biggest plus is it would be someone under 60! I realize this is all fantasy, but someone brought this up in the comments of a post about her urging people to vote and I can’t stop thinking about it.