Yesterday's Enterprise: How is the Federation Losing So Badly?

[Nob Akimoto]

We know that as of 2366 in the alternate timeline the Federation is facing defeat within 6 months and that 40 billion people have died. Some other observations from within the episode suggest:

1. The Enterprise-D despite being a "warship" is wandering around hostile space without an escort. When we're later treated to Galaxy-class ships in a warship role (in DS9), they were evidently part of larger formations of ships called "wings" akin to task groups or squadrons. The fact that the E-D is alone might give some indication of just how badly the war is going for the Federation.
   
2. Although referred to as a "warship", the Enterprise-D still looks quite similar to the one in the "proper" timeline. Although she has a substantially different bridge module, the basic structure of the ship is the same. This suggests the war started while the Galaxy-class design project was pretty far along, perhaps not as long as the "20 years of war" figure bandied about in the episode.
   
3. Yar notes that the Enterprise has been in service for around 4 years at that point, which might mean that she was rushed into service with minimal internal fittings. (Like described of other Galaxy-class ships in the DS9TM). The fact that they seem to have reduced power to give to things like replicators suggests she's at least a much more spartanly equipped vessel.

Some additional extrapolations from official sources:

• The total casualty figures are surprisingly close to the Borg invasion of 2381. 63 billion vs 40 billion isn't a rounding error, but it is similar enough to give some sense of just how devastating the war has been on the Federation. Given that it's unlikely the 20 year war would've included massive bombardments of several key Federation worlds in the same way the Borg hit out, the casualties were probably far more spread out and suffered in a war of attrition or attacks on civilian infrastructure.
  
• Klingons may or may not have wiped out the Betazoids in this timeline.
  
• Since this predates the creation of some powers like the Cardassians, they aren't explicitly mentioned, but given the Federation was in active conflict with both them and the Tzenkethi in the 2350s, it's likely that they were also fighting the Federation along with the Klingons.

It seems likely to me, that the decline of the Federation in this timeline probably stems from having to fight a multi-front war while facing a power with rough parity like the Klingons. It seems unlikely that simply going to war with the Klingons would put the Federation so badly on the back foot, especially since (although some 2 generations earlier) the military brass in the 2290s were confident the Federation could "clean the chronometers" of the Klingon Empire and the weakness of the Klingons in general around the Praxis incident.

 

[Unicron]

I suppose in part it might also depend on whether you only wanted to go by canonical data, or wanted to include other possibilities as well. Going by what FASA wrote, there had already been one major war between the UFP and the Klingons (the Four Years War) by the time of TOS, and another war was just breaking out when the Organians imposed their terms on both sides. It's implied that the two powers are roughly equal in strategic terms, so in the event of a future war it's not inconceivable the Klingons could have gotten an edge.

It's also up for grabs what sort of covert help either side might have gotten, if any. The Romulans might have backed the Klingons once the war started to go in their favor, as Sela's forces supported the Duras family during the Klingon civil war. The Enterprise-C is consistently referred to as an "old" design by military standards, and Yar says that the Federation has lost half the fleet to the Klingons by the alternate 2366. Perhaps the Klingons would have been more willing to do what the Jem'Hadar often did and make kamikaze attacks a part of their tactics?

 

[Nob Akimoto]

The kamikaze thing is a good point, but I'm kind of curious as to why then, the Klingons seemed so eager to capture the Enterprise. Also, we saw that they were using (grossly inflated) Birds of Prey of some sort, so they weren't exactly technologically super advanced, even if 3 of them were able to take out the Enterprise. (Do wish they'd replaced the "K'Vorts" when they made TNG-R, alas...)

The interesting bit might be the lack of Worf. I used to think they missed an opportunity by not making Worf the commander of the Klingon task force, but with more thought, I think the fact that he's not around (and presumably wasn't rescued from Khitomer) gives some more weight to the Romulans manipulating the Klingons, especially with the level of Romulan interactions with the Duras family which wouldn't have the House of Mogh in any form to counter them.

 

[blssdwlf]

It could be also because the military arm of Starfleet was retired after The Undiscovered Country and the Starfleet of Enterprise-C's time lacked the ability to wage a war with the Klingons. Compare that to DS9 where the Federation had to increase their military training to deal with the Borg and thus were more prepared for the Dominion.

 

[Nob Akimoto]

Yeah, but the DS9 era Starfleet still was using huge numbers of Narendra III vintage ships. (Excelsiors, Mirandas etc)

Also, presumably Starfleet was fighting border wars during that time with Cardassians and Tzenkethi at the very least, so they weren't entirely out of training for threat scenarios.

 

[Crazy Eddie]

Couple of things here.

First of all, it has to do with the nature of "space war" in general. Both the Federation and the Klingons only ever fight wars over disputed planets that both of them seem to want. The Klingons generally haven't set their sights on that many planets that are claimed by the Federation other than Arkanis and a handful of others; if they were going to war at all, it would be over those.

So how does that war stretch out to more than twenty years, all because of the Battle of Narendra-III? That suggests the "war" as we understand it is more complex than we really believe and a lot's going on in the background that isn't being mentioned.

In which case:

It seems likely to me, that the decline of the Federation in this timeline probably stems from having to fight a multi-front war while facing a power with rough parity like the Klingons. It seems unlikely that simply going to war with the Klingons would put the Federation so badly on the back foot, especially since (although some 2 generations earlier) the military brass in the 2290s were confident the Federation could "clean the chronometers" of the Klingon Empire and the weakness of the Klingons in general around the Praxis incident.

Meaning it probably isn't just the Klingons. Just a couple of years after the Narendra-III massacre, the Federation and the Klingons are at war.

Picard knows about the Romulan attack in the prime timeline, but not in the new one. It's likely that the Romulans were in the process of forging an alliance with the Federation at the time, aggravating the relatively peaceful relations with the Klingons. A squad of Romulan warships slaughtering a Federation starship would have torpedoed (literally) any such alliance and resulted in the Klingons cozying up to the Federation in an "enemy of my enemy" sort of relationship. But if nobody knows the Romulans killed the Enterprise, that alliance might have finally come to pass.

20 years ago, that would have cleared the way for a Romulan invasion of the Klingon Empire (of which the Khitomer Massacre would have been merely an opening move). Hard to say where that goes after twenty years, but it seems evident that the Klingons not only survived the Romulan invasion, they recovered enough that they are now seeking revenge against anyone and everyone who ever supported the Romulans in any way shape or form. It's likely that most of that war involved the Federation and the Romulans teaming up against an increasingly powerful Klingon military; the current "downfall" stage of the war is a consequence of the Klingons finally overcoming the Romulan empire, glassing Romulus and then turning to the Federation saying "And now it's YOUR turn!"

Also, I'm pretty sure that Deanna Troi was part of the Enterprise crew when it was first commissioned. She was killed by Armus on Vagra-II in an attempt to get an emotional rise out of the Enterprise rescue team (Deanna, being the only person on the entire crew with a high regard for sentient life).

 

[Crazy Eddie]

It could be also because the military arm of Starfleet was retired after The Undiscovered Country

It wasn't. Stop saying that.

 

[C.E. Evans]

I always saw the (initial) Khitomer Accords as being a cease-fire agreement that allowed the Klingons to rebuild both Qo'noS and their overall economy following the Praxis Disaster. By the 2340s, the Klingons achieved this and hostilities with the Federation eventually resumed sometime later, escalating in time to a protracted war.

In this war, the Federation could have been weakened over time by a sizeable number of war-weary member worlds deciding to secede and perhaps sign non-aggression pacts with the Klingons and/or by the destruction of many key production facilities, losing a great deal of its war machine infrastructure.

Although referred to as a "warship", the Enterprise-D still looks quite similar to the one in the "proper" timeline. Although she has a substantially different bridge module, the basic structure of the ship is the same. This suggests the war started while the Galaxy-class design project was pretty far along, perhaps not as long as the "20 years of war" figure bandied about in the episode.

If we go by ye old TNG Tech Manual, the Galaxy Class Development Project was already underway by 2343 (supposedly a year prior to Narendra III according to Okuda's chronology). But the conflict between the Federation and the Klingons could have driven the design's mission from originally being a multipurpose exploration ship to it now being a troop transport, intended primarily to carry thousands of combat personnel to wherever they were needed.

"[The Enterprise-D] was the first Galaxy Class warship built by the Federation. Forty two decks. Capable of transporting over six thousand troops."
--Lieutenant Tasha Yar

It seems to suggest that in this timeline, the USS Galaxy was renamed USS Enterprise-D during her construction, but her design retained the name Galaxy-class.

In any event, I think the Galaxy-class was always meant to have "battleship-grade" capabilities, and that the war with the Klingons merely called for the reduction of resources (personnel & onboard facilities) dedicated solely for scientific research and the total elimination of spouses and children (the presence of Guinan, however, tends to suggest that at least a very limited number of civilians could still serve aboard fleet vessels in a support capacity, perhaps at a captain's discretion).

 

[blssdwlf]

It could be also because the military arm of Starfleet was retired after The Undiscovered Country

It wasn't. Stop saying that.

It was. Stop trying to claim otherwise unless you've got proof.

MILITARY AIDE: Bill, are we talking about mothballing the Starfleet?
C in C: I'm sure that our exploration and scientific programs would be unaffected, Captain, but...
​

 

[blssdwlf]

Yeah, but the DS9 era Starfleet still was using huge numbers of Narendra III vintage ships. (Excelsiors, Mirandas etc)

Yes, because they had time to get those 100s or if not 1000s of ships out of mothballs. Think of the times in TNG when they had little warning and could barely scrape together 30 or 40 ships.

Also, presumably Starfleet was fighting border wars during that time with Cardassians and Tzenkethi at the very least, so they weren't entirely out of training for threat scenarios.

True, but border wars don't seem like they need that many ships, IMO.

 

[bullethead]

In general, we see a pretty consistent trend of Starfleet incompetence post-TUC, starting chronologically with the fact that Starfleet was completely ignorant of the Nexus passing by Earth until the Enterprise-B received a distress call from ships trapped in it. So it wouldn't surprise me that Starfleet was overextended by exploration in the early days of the war and lost tons of ships, facilities, and planets before they consolidated their forces and managed to slow down the Klingon advance.

 

[C.E. Evans]

In general, we see a pretty consistent trend of Starfleet incompetence post-TUC, starting chronologically with the fact that Starfleet was completely ignorant of the Nexus passing by Earth until the Enterprise-B received a distress call from ships trapped in it.

To be fair, no one in Starfleet even knew what the Nexus was until Guinan finally told Picard in Generations. At the time of the Enterprise-B, it was believed to be a powerful energy/gravimetric distortion--one of many space anomalies (a.k.a. weird stuff) that pop up randomly across the Galaxy from time to time.

 

[Nob Akimoto]

Just answering the points raised in responses.

• Given that we know the Federation had no contact with the Romulans after the Tomed Incident in the 2310s, I don't think it makes sense to assume there were Fed-Romulan negotiations going on at the time. What's more likely there I think is the Romulans see the Feds and Klingons at war, also have someone sympathetic to them on the High Council (Duras) and decide to capitalize on that and offer to aid the Klingons in some fashion.
  
• I always assumed Yar's line meant that the Enterprise was simply the first Galaxy-class ship outfitted as a warship, hence the very large troop complement and minimalist interior. (It would then also explain how she was in service a year earlier, if they decided to try a warship configuration without all the odds and ends put into Galaxy and Yamato.
  
• The conversation about "mothballing" Starfleet never made a lot of sense outside of it being the typical bureaucratic scare-mongering that institutions like the military like to do. Afterall the end of the Cold War and even the recent budget sequester have also been likened to dismantling the entire military when clearly that hasn't been the case.
  
• Starfleet evidently is substantially more dispersed in the 24th century as it gets larger commitments. The E-B being the only ship to help the El-Aurian refugees, having time to only cobble 40 ships together in a fleet for Wolf 359, etc. all suggest that Starfleet has a lot more cubic lightyears of space to cover than they have ships.
  
• Even if the Tzenkethi and Cardassian conflicts start as border conflicts, if the escalation of the Klingon War in the 2350s would probably give them sufficient reason to mass large groups of ships to take some strategic star systems and possibly take out some Starbases.
  
• A "Sneak Attack" type situation from the Klingons might be possible, if Starfleet Intelligence is completely asleep at the wheel and they make good use of cloaks. I think it was in Star Fleet Battles where the Klingons manage to isolate and destroy a fair number of the Federation's main ships of the line before the Organians stopped the war.

 

[Praetor]

For Narendra III to plausibly be a single turning point that so easily changes things, we need to have a long history of animosity and almost-wars, which we do indeed have. I do think it's safe to say that the first Khitomer Accords were basically just a cease-fire, not a treaty of alliance of any kind. Basically, a promise to leave one another alone and probably some one-time industrial assistance from the Federation to the Klingons in exchange for something the Federation wanted.

I think it's also important to remember that the Federation/Klingon conflict was long a metaphor for the Cold War. Fundamentally, the Federation and Klingons have completely opposing ways of life. The Federation largely thought of the Klingons as brutes, and the Klingons largely thought of the Federation as honorless weaklings. The Klingons, being the more aggressive, would need to be the ones convinced otherwise first, and I doubt a cease-fire would do anything to achieve that.

What's interesting to me is that Starfleet knew the Enterprise-C was lost near Narendra III, but didn't know about the Romulans. Just how did the Federation think the C was lost? And who did they think destroyed the Klingon outpost? I could easily see the Klingons finding out about the C somehow, and accusing the Federation of destryoing Narendra III. The Federation, of course, would deny it, and probably begin to suspect the Klingons destroyed the Enterprise.

I mean, think about that a second. You're a Federation citizen, and you hear that the Klingons are accusing one of your ships of destroying one of their colonies, and it's the Enterprise! Not only that, but she was lost. "The bastards probably destroyed her. They've hated the Enterprise name ever since that Kirk guy showed them what idiots they are." With that kind of mutual accusation and suspicion, I think war was inevitable.

And just what were the Romulans doing? We know that the Romulans attacked at least one other outpost during this time, Khitomer. It appears that there was bad blood between the Empires since the original alliance, and yet the Duras family was eager to cooperate with the Romulans for their own gain. Did the Romulans then know that if they could attack colonies along the border they might be able to destabilize the situation between the Federation and Klingons? War between her two greatest enemies would surely only benefit the raptors. In the Prime timeline, perhaps the Khitomer attack was another attempt at doing the same thing they tried to do at Narendra III. Perhaps in the altered timeline, another attack wasn't necessary, and thus no Worf in Starfleet. Then again, perhaps there was an attack on Khitomer and it made the situation that much worse.

All wars must have an eventual victor, though. Between the Federation and the Klingons, who would the Romulans really want to come out on top? I would wager the Klingons. Though they probably see them as violent brutes, I would argue the Romulans would say they are dumb enough to be manipulated where the Federation is not. Therefore, there's a likelihood of the Romulans providing some material assistance to the Klingons through channels such as the Duras family, but remaining officially neutral. The raptors become vultures.

Add to that the fact that Starfleet is consistently depicted as widely dispersed. If I had a nickel for every time the Enterprise was the only ship in the <insert space measurement unit here> I could buy my own Enterprise. Then, add the fact that we appear to see great growth in the Federation during the early 24th century, and the other conflicts we know were ongoing; Cardassian, Tzenkethi, and possibly Tholian per "The Icarus Factor." As others have said, Starfleet was probably over-extended in her commitments during this time, awaiting a straw on her back to break her.

Technologically, the Vor'cha class visually suggests the Klingons benefitted from their alliance with the Federation. Does this then mean that the Empire's warships were inferior? Perhaps. But technological superiority certainly doesn't guarantee Federation victory. Klingon ships are oriented primarily for war, where Federation ships historically were not.

And let's not underestimate the Klingons themselves. These are a people who glorify conquest and death, and who by their very way of life embrace war and fighting. The Federation and Starfleet, though I by no means believe them to be the extreme doves they are sometimes depicted to be, are reluctant to face war. The Klingons are vicious. Kamikaze tactics in the face of defeat are established, notably per Worf in "First Contact." Even if Federation ships could overpower Klingon ships technologically, the Klingons would surely take their vengeance in almost every lost encounter via kamikaze tactics.

And I would also throw out there the fact that "twenty years of war" doesn't have to mean that they were in open war for all of those years.

 

[blssdwlf]

• The conversation about "mothballing" Starfleet never made a lot of sense outside of it being the typical bureaucratic scare-mongering that institutions like the military like to do. Afterall the end of the Cold War and even the recent budget sequester have also been likened to dismantling the entire military when clearly that hasn't been the case.

If you examine the US Navy's ship force levels after the end of the Cold War you'll find that the navy downsized from 500+ to 300+. During the height of the Cuban Missile Crisis the navy had nearly 900 active ships. During WW2, 6000+.

So if you can imagine Starfleet having to deal with hostile Klingons for 70 years then going to a peace-time stance there is plenty of opportunity at that point to retire most of their military ships and downsize to just exploration and science oriented ships. With fewer ships you get the "overstretched and overreached" Starfleet in TNG trying to police their own space.

The other thing to also consider is with a changed Starfleet comes changed training priorities. As Riker put it in "Peak Performance", combat training isn't high on their priorities:

RIKER: I prefer brains over brawn as well. I think it's a waste of effort to test our combat skills. It's a minor province in the make-up of a starship captain.
​

And this is proven when Riker while in charge of the E-D gets defeated by two BOPs run by Ferengis. IIRC, even Odo makes fun of this.

But if you go back to the Klingons we know that they have very long lives. Kor, Kang and Koloth and all their generation of warriors would've been able to contribute to battling the Federation whereas Starfleet would be in a scramble to train up new warriors.

 

[Unicron]

Picard knows about the Romulan attack in the prime timeline, but not in the new one. It's likely that the Romulans were in the process of forging an alliance with the Federation at the time, aggravating the relatively peaceful relations with the Klingons. A squad of Romulan warships slaughtering a Federation starship would have torpedoed (literally) any such alliance and resulted in the Klingons cozying up to the Federation in an "enemy of my enemy" sort of relationship. But if nobody knows the Romulans killed the Enterprise, that alliance might have finally come to pass.

20 years ago, that would have cleared the way for a Romulan invasion of the Klingon Empire (of which the Khitomer Massacre would have been merely an opening move). Hard to say where that goes after twenty years, but it seems evident that the Klingons not only survived the Romulan invasion, they recovered enough that they are now seeking revenge against anyone and everyone who ever supported the Romulans in any way shape or form. It's likely that most of that war involved the Federation and the Romulans teaming up against an increasingly powerful Klingon military; the current "downfall" stage of the war is a consequence of the Klingons finally overcoming the Romulan empire, glassing Romulus and then turning to the Federation saying "And now it's YOUR turn!"

This is an interesting idea, and one I hadn't thought about much before. Perhaps the Romulans weren't necessarily conquered, but did bow out when they felt there was little chance of winning (or if the Klingons gave them a reason to do so). I'd also agree with Praetor that we don't know if the war lasted a full twenty years or so, though I'd wager it did last a good length of time for the Federation to have lost so much by 2366.

Also, I'm pretty sure that Deanna Troi was part of the Enterprise crew when it was first commissioned. She was killed by Armus on Vagra-II in an attempt to get an emotional rise out of the Enterprise rescue team (Deanna, being the only person on the entire crew with a high regard for sentient life).

I'd respectfully disagree here. While this is certainly one possibility in the alternate timeline, I think it's more plausible that the Enterprise crew never performed some of the same missions and never visited Vagra II because Troi's shuttle was never there. She could be anywhere in the alternate Federation, and I think this fits better with the presence of the alternate Yar (whose counterpart was killed by Armus in the main timeline, but not here) and some of her statements about serving on the Enterprise.

 

[Nob Akimoto]

Deanna being dead might go a good way to also explaining Picard and Riker's....rocky....relationship.

We all know that in every timeline that Riker is a bitter asshole, it's probably because Deanna died at some point or wasn't around.

 

[Nob Akimoto]

If you examine the US Navy's ship force levels after the end of the Cold War you'll find that the navy downsized from 500+ to 300+. During the height of the Cuban Missile Crisis the navy had nearly 900 active ships. During WW2, 6000+.

So if you can imagine Starfleet having to deal with hostile Klingons for 70 years then going to a peace-time stance there is plenty of opportunity at that point to retire most of their military ships and downsize to just exploration and science oriented ships. With fewer ships you get the "overstretched and overreached" Starfleet in TNG trying to police their own space.

The other thing to also consider is with a changed Starfleet comes changed training priorities. As Riker put it in "Peak Performance", combat training isn't high on their priorities:

RIKER: I prefer brains over brawn as well. I think it's a waste of effort to test our combat skills. It's a minor province in the make-up of a starship captain.
​

And this is proven when Riker while in charge of the E-D gets defeated by two BOPs run by Ferengis. IIRC, even Odo makes fun of this.

But if you go back to the Klingons we know that they have very long lives. Kor, Kang and Koloth and all their generation of warriors would've been able to contribute to battling the Federation whereas Starfleet would be in a scramble to train up new warriors.

Starting with the longevity.

We know that humans aren't exactly the longest lived members of the Federation by a long chalk, with several species that live substantially longer lives. Vulcans at least live into their third century if they don't get sick with odd strange illnesses, and there's a bunch of other species that have longer lifespans. For that matter it's evidently not at all extraordinary for human Starfleet officers to be in service as centenarians. I don't think it's at all likely for them to have much trouble coming up with trained warriors, especially when there's several Starfleet member planets with strong military traditions like the Andorians.

Second, US Navy Force levels between the Cold War and modern USN aren't particularly helpful when you look at the composition of the ships employed. A modern DDG could wipe the floor with a squadron of Cuban Missile Crisis era frigates and destroyers, or cruisers for that matter. While downsizing was very real, if you note how the force composition changes the difference between 89 and the late 90s boils down to:

• Removing all the battleships from service.
• Decommissioning CGNs and CGs in favor of newer aegis equipped DDGs as their refueling cycles or SLEP cycles came up. (Decommissioning of Belknap and the 3 CGN classes that were well into their third decade of service and replacing them with more capable DDG-51s)
• Significant reduciton in the number of auxiliary ships.
• Reduction in number of lower performing ships like FFs (like the Knox-class) in favor of increasing proportions of more Burke-class DDGs.

In Starfleet terms it might mean that after the Khitomer Accords, Starfleet demobilized a significant portion of its less useful/flexible ships in favor of ramping up construction of more capable and flexible cruisers. This would coincide with a huge building program of Excelsior and Miranda class ships filling in for all the FASA and FJ auxiliaries and ships of dubious utility.

Also re: Rascals, we know the scenes used for that episode were reuses of the Klingon K'vorts attacking the Enterprise-D in Yesterday's Enterprise, so perhaps those were the very big warship type BoPs retrofitted with more advanced weaponry. Combined with the fact that the klingons are ostensibly allies, and they were in the middle of a delicate rescue operation I'd imagine it's not really Riker's fault that they were caught flatfooted. We know at least that Riker's presence (and tactical acumen?) were considered so vital by Q that he claims no William Riker would have led to no Federation after Wolf 359, and he seemed to have no trouble outmaneuvering the So'na. (The latter granted after a bunch of years of war)

Further in hand to hand combat Starfleet officers seemed more than capable of holding their own against Klingons circa 2370 (Way of the Warrior), so I don't think the "they let their military training lapse" thing really works as a reason.

 

[blssdwlf]

I'm going to start back again with numbers.

Second, US Navy Force levels between the Cold War and modern USN aren't particularly helpful when you look at the composition of the ships employed.

To me it's more a numbers game. If we kept up the same number of ships from the Cold War and continued to upgrade them, we'd have more capable ships today. Instead we have far fewer ships and that means we're less able to absorb losses if we were to be involved in a war.

A modern DDG could wipe the floor with a squadron of Cuban Missile Crisis era frigates and destroyers, or cruisers for that matter.

Ah but I'm not talking about old vs new. I'm talking about numbers of ships. (And to your argument, "A modern DDG could wipe the floor with a squadron of older ships" but a squadron of modern DDGs will wipe the floor with a squadron of older ships.)

In Starfleet terms it might mean that after the Khitomer Accords, Starfleet demobilized a significant portion of its less useful/flexible ships in favor of ramping up construction of more capable and flexible cruisers. This would coincide with a huge building program of Excelsior and Miranda class ships filling in for all the FASA and FJ auxiliaries and ships of dubious utility.

A significant portion being mothballed could mean leaving behind a majority of ships not optimized for combat stuck being used for wartime needs during the war in "Yesterday's Enterprise".

Also re: Rascals, we know the scenes used for that episode were reuses of the Klingon K'vorts attacking the Enterprise-D in Yesterday's Enterprise, so perhaps those were the very big warship type BoPs retrofitted with more advanced weaponry. Combined with the fact that the klingons are ostensibly allies, and they were in the middle of a delicate rescue operation I'd imagine it's not really Riker's fault that they were caught flatfooted.

My assumption has always been those BOPs had modern weaponry. The problem is that Riker was not caught flatfooted. If you watch the episode, he takes an inexplicably long time to order the ship to return fire and his combat performance was underwhelming in that battle.

We know at least that Riker's presence (and tactical acumen?) were considered so vital by Q that he claims no William Riker would have led to no Federation after Wolf 359,

I think Riker's required presence was more from his unconventional thinking that lead to decisions that helped to stop the Borg. That's handy when it's not a conventional war but his conventional fighting record isn't so good.

edit: Although we do see in "Parallels" where there was an E-D and a scraggly William Riker and the Borg had won. So Q might not have been 100% right.

and he seemed to have no trouble outmaneuvering the So'na. (The latter granted after a bunch of years of war)

The battle with the So'na and to the same extent with the Ferengi BOPs resulted in a badly damaged Enterprise requiring him to resort to unconventional tactics to survive. I'd argue that if he was a better combat captain his wins would've came earlier and less damage to his ship.

Further in hand to hand combat Starfleet officers seemed more than capable of holding their own against Klingons circa 2370 (Way of the Warrior), so I don't think the "they let their military training lapse" thing really works as a reason.

"Way of the Warrior" came a couple of years after "Peak Performance" which would indicate Starfleet recognizing their lack of combat readiness and attempting to improve upon it through additional training. It would make sense that by "Way of the Warrior" we should see some competent Starfleet officers in hand-to-hand combat.

But let's go back to "Yesterday's Enterprise." I found wartime Picard's combat curiously bad as well. He didn't attempt to reduce the number of enemy ships prior to them closing to point-blank range. He spent alot of time giving directional orders when he should've just ordered "phasers and torpedoes, continuous fire". Compare that to fire everything and keep firing until you're empty Picard in "Nemesis". To me it points to a different training experience (or lack of) for the "Yesterday's Enterprise" Picard.

Now back to longevity.

Starting with the longevity.

We know that humans aren't exactly the longest lived members of the Federation by a long chalk, with several species that live substantially longer lives. Vulcans at least live into their third century if they don't get sick with odd strange illnesses, and there's a bunch of other species that have longer lifespans. For that matter it's evidently not at all extraordinary for human Starfleet officers to be in service as centenarians. I don't think it's at all likely for them to have much trouble coming up with trained warriors, especially when there's several Starfleet member planets with strong military traditions like the Andorians.

You make good points with the Vulcans and Andorians but did you consider that they would only makeup a small portion of Starfleet? A low percentage of experienced, combat-oriented crews for Starfleet vs the entire combat-oriented Klingon crews of the Klingon navy.

Although there are references to the Tzenkathi and Cardassian conflicts, they just don't seem to have motivated Starfleet like "Q Who?" did or as Picard put it, "Well, perhaps what we most needed was a kick in our complacency, to prepare us ready for what lies ahead."

I don't think you can discount numbers and experience and that can go a long way in explaining why Starfleet was losing so badly in "Yesterday's Enterprise", IMHO.

 

[Praetor]

blssdwlf, fully agree with much of what you said, particularly this:

Ah but I'm not talking about old vs new. I'm talking about numbers of ships. (And to your argument, "A modern DDG could wipe the floor with a squadron of older ships" but a squadron of modern DDGs will wipe the floor with a squadron of older ships.)

On the latter, this is how I've always thought about the effectiveness of the Miranda class, particularly in her 23rd century heyday. She's got a lot of weapons emplacements, but odds are being smaller she's probably not quite as powerful as the Constitution. Still, even in the 24th century, a swarm of them could surely take down a bigger ship.