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Cruel Optimism and Points of Diversion

Ysengrimus

Active member
So I'm reading a book by Lauren Berlant called Cruel Optimism. The idea behind the title, the core concept, can be easily explained with this quote:

"A relation of cruel optimism exists when something you desire is actually an obstacle to your flourishing. It might involve food, or a kind of love; it might be a fantasy of the good life, or a political project. It might rest on something simpler, too, like a new habit that promises to induce in you an improved way of being. These kinds of optimistic relation are not inherently cruel. They become cruel only when the object that draws your attachment actively impedes the aim that brought you to it initially."

I am curious about, since we are historians and alternate history historians at that, the idea of cruel optimism. We are aided in this by the powerful tool called hindsight. When is your favorite case of cruel optimism in alternate history? I'll give an example.
-Bayezid I takes Constantinople in 1402. This is a bit more of a poison-pill than one might think, as demonstrated in this other thread here. By taking what he wanted, Bayezid may have made Ottoman empire ultimately weaker and less able to expand, with multiple Byzantine heirs in the winds and the promise of a series of embargoes and possible attempts to re-install them from European power.
- The Mongols take Northern China easily, instead of the decades-long slog they actually had to deal with. In my estimation, they'd be so busy plundering and exploring North China, that they might not turn their attention to the Kwazerim Empire--or expand in that direction. By trying to loot North China early, it seems likely that the Mongols would try to settle themselves there, thus falling into the classic flaw of the nomad people when they come into close contact with sedentary cultures.
What do you guys think? Favorite moments of cruel optimism in history/alt-history?
 
A tamer one sports in actual history.

The David Robinson San Antonio Spurs were one of those "always made the playoffs, a longshot-to-slight underdog contender to win the championship" teams.

In the 96-97 season OTL, Robinson got hurt, the Spurs then wrote off the season in the hopes of getting the no. 1 draft pick-which they did. Cue Tim Duncan and the beginning of five titles and constant contention for more than a decade. If that doesn't happen and they repeat their pattern, even if they win a championship (likely against Jordan's Bulls), they will not be in the draft lottery (meaning someone else will get Duncan, probably with equally poor long-term results for his career) and the chance of a dynasty becomes a lot smaller.
 
If at least one elector votes Jefferson / Some Rando in 1800, Aaron Burr doesn’t come within spitting distance of the presidency - doesn’t ruin his reputation by intriguing with the Federalists and subsequently blaming Hamilton for all of it and killing him - and eight years later Burr is a two-term VP at a point in time when every VP has ascended to the presidency, the obvious choice of Democratic-Republicans that don’t want to continue the Virginia Dynasty, and the odds-on favorite to be the next President of the United States.
 
Labour Together's report in the 2019 election is saying this happened after 2017: doing better than expected made too much of the party complacent and led to a greater defeat two years later.

And arguably the way May came to power, coming off the Tories winning quite handily in 2015, caused the same problem for the Conservatives in 2017.
 
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