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Is it really credible that the Federation would be fighting a losing war with the Klingons after twenty years? Why were the Klingons winning? What happened to the Romulans? Why would a Romulan attack on a Klingon colony cause a war between the Klingons and the Federation in the first place?

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    lots of questions here - the last one is directly answered in the episode: - chakoteya.net/NextGen/163.htm --- "GARRETT: We were responding to a distress call from the Klingon outpost on Narendra Three. PICARD: The Narendra Three outpost was destroyed. It is regrettable that you did not succeed. A Federation starship rescuing a Klingon outpost might have averted twenty years of war." Basically, the Klingons called on the Federation for help - they didn't come. Honor was hurt = war – NKCampbell May 4 '18 at 2:54
  • Wait, Klingons asking for help from humans? Ehm, maybe I remember incorrectly about how they think. – Mr Lister May 4 '18 at 5:32
  • I don't think it would be too surprising that a warrior race would gain the upper hand in a prolonged, protracted war. Klingons are born to fight and conquer (to steal a line from an old video game). They probably likely had a certain material advantage from using slave labor on conquered worlds for construction and supplies. – Helbent IV May 4 '18 at 5:37
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    @NKCampbell I think it was more that Federation assistance during the attack on Narendra III in the prime timeline caused the Klingons to respect the Federation enough to prevent war rather than lack of assistance causing the war. – HorusKol May 4 '18 at 9:04
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    @MrLister I doubt the Klingons were specifically requesting human aid, it was more likely a general distress call that the Enterprise-C intercepted and decided to respond to. – Brandon Dybala May 4 '18 at 16:58
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The easiest to answer of those questions would be the last one, which had an entire episode to answer it. "TNG: Yesterday's Enterprise" main plot was that it wasn't about the Romulan attack on Narenda III causing a Federation-Klingon war. It was about the act of the Federation sacrifice to defend the Klingons had the diplomatic power to prevent a later Federation-Klingon war. The reoccurring theme throughout the Original Series and the first six movies was the threat of the Klingons. In the briefing room scene at the beginning of Star Trek VI, Spock references that there was "seventy years of unremitting hostility with the Klingons". These two powers were on the brink of war for nearly a century. In the Yesterday's Enterprise's (YE) timeline, it's not hard to believe that just another decade or two of tension finally erupted somewhere into total war.

The movies also prove the example of the threat that Klingon ships posed. In Star Trek VI, although the Klingons had a huge (initial) advantage of a battle cloak, a single Bird of Prey was able to inflict significant damage against a Constitution and Excelsior class starship. Considering that the D7 Cruiser was the Klingon's real ship of the line, the Klingon fleet was definitely a match for Federation Forces. Again, it's not that much of a stretch in the YE timeline for one or two critical engagements to go poorly for the Federation, and start a slide towards eventual defeat.

As for the Romulans, it's has also been a recurring theme of Star Trek that all three powers are not fond of each other. The Klingons and Romulans were definitely not fond of one another. So why would they enter a war where two of their enemies were weakening each other and save one of their rivals?

The hardest question to answer is the first one. There was no reference as to how the Federation came to be doing so poorly in the war. The best that can be accomplished is pure speculation. However, twenty years of warfare can grind any economy to dust. Considering how much of a threat the Klingon ships posed tactically, and how the Klingons could fare better in an extended war with their warrior culture, all it would take would be a Battle of Midway type battle that would begin putting the Klingons at an advantage. Regardless, it was an alternate timeline, and a pretty badass one at that.

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    The Klingons were definitely getting the better of the Federation in Discovery, and I had the distinct impression they were starting to get the better of the Federation in the Klingon-Federation war in DS9, too, before it came to an unexpected end. I think they just have a natural advantage. As you say, this is probably mostly due to the cultural differences. – Harry Johnston May 4 '18 at 4:53
  • Right? I haven't watched Discovery myself, and I was afraid to use any sources that dated after the episode in question, but those are both valid points. – as.beaulieu May 4 '18 at 16:37

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