Time Frame: Set just before "In the pale moonlight" (When the Romulans join the alliance).
Setting: You have just been elected the new leader of a small yet moderately powerful species on the Federation/Gorn/Klingon boarder as shown below.
You have considerable individual power but any major changes and political moves have to be pushed through the senate.
Your species controls a dozen systems, four of which have habitable planets. You have a population of around 100 Billion, the population is spread across one Homeworld with a highly built up population, two other planets with moderately built up planets, and 3 planets with low levels of habitation.
Your species main claim to fame is Matter/Anti-Matter production. You have developed and maintained the most efficient form of anti-matter production in the quadrant. You supply some stock to the Klingons and occasionally the Federation although they tend to supply their own. You supply almost the entire stock of anti-matter to the Gorn and you are the primary supplier to almost every private space going organisation in space (cargo companies ect).
Your production facilities are on a single Mars like planet in your core system under heavy guard.
Military: You have a modest military, your technology is at par with Federation technology during 2330 (40+ years before DS9).
You allied with the Gorn during one of their wars with the Tholians, which has earned you a strong ally with them and an enemy of the Tholians. You are occasionally bothered by raiders as are all powers but you face more than your fare share of Klingon rouges.
What do you do?
You have been approached by both the allies and Dominion to ally with them.
The entire quadrant is about to be engulfed in war. Your sworn enemies the Tholians have signed a NAP with the Dominion. The Gorn have yet to commit to either side. Your neighbours, two of the quadrants superpowers (Klingons, Feds) are at war while the third superpower (Romulans) is under NAP.
What does defeat mean to you?
Nothing it will never come. Death before defeat. I don’t bend or break. I end, if I meet a foe capable of it. Victory is in forcing the opponent to back down. I do not. There is no defeat.
I'd go a couple of ways, depending on how the neighbouring powers would respond to my requests.
First I talk to the Allies:
Now, they want me on their side, and it's clear that the war is going against them, so they need allies. I let them know I'll be willing to provide some support against the Dominion on a few conditions:
1) I want 20-30 systems ceeded to my empire from Federation or Klingon space. All inhabitants will be removed by whoever was formerly in control of the planets.
2) I want financial support, quite a bit.
3) I want technology.
So, either they accept, and I join and offer up only a token resistance to the Dominion while keeping the majority of my fleet around my homeworlds as 'security' against a Dominion attack and enjoy the new wealth and resources I've grabbed us. By the time the war ends, my small empire will be set for the forseeabel future, with large amounts of territory and resources and money. I'll likely be known among my own people as a national hero, and known as "that thieving bastard" among the Feds and Klingons.
Or the don't accept, in which case I inform them that I have no intentions of allying with the Dominion, and am happy to sit out in neutrality.
Then I talk to the Dominion (assuming the Feds declined my previous offer, that is).
I tell them that I'd love to ally with them, but doing so would result in me getting completely curbstomped by the Allies, so it's not an option. I get warm relations with them, and am more than happy to supply them with my M/AM stuff in exchange for money and technology. This way I can happily sit out the war selling fuel to both sides of the war.
Now, the Feds and Klingons are likely to get quite irked at this if they ever find out about my deals with the Dominion, so time to go chat to the Gorn.
I tell them that I'm staying neutral in this conflict, and urge them to do the same. Now, I also begin to warn them that we stand a good chance of being invaded by the Dominion, as evidenced by their expansionist pollicies. I get them to sign a mutual defence pact with me, meaning that if one of us is attacked, the other must come to help. I also word the treaty so that it can apply to an attack from any power, not just the Dominion.
Now, assuming the Feds/Klingons find out that I'm supplying the Dominion as well as them, they may decide to launch an attack to wreck my production facilities. If they do so, I call on the treaty and get the Gorn over here to help defend myself against this "unwarranted aggresion".
If they agree, then I warn the Federation that further aggresion from them or the Klingons will be considered an act of war, and we will ally with the Dominion. They can't affor a war on two fronts, even if they could curbstomp us horribly, so they'll likely lay off, leaving me to my plan of sitting back and getting rich off both sides of the war.
Of course, the Gorn could always just say "Hey, you pissed the Federation off, it's your problem, so don't expect us to deal with it.". Except then I say "Oh, well, that's too bad, but I don't mind too much. Oh, and by the way, all M/AM shipments to your nation will be halted for the forseeable future as I need them to defend my own nation. I've no idea when we'll be able to resume trade, though it'll probably not be for a long time.". Now, this means that the Gorn are in trouble, because I'm their primary supplier. They have to help me, otherwise they're going to run out of fuel very quickly, leaving them totaly defenceless against their Tholian enemies.
So, in either case I exploit what's going on, and sit back and relax for the rest of the war.
"You've all been selected for this mission because you each have a special skill. Professor Hawking, John Leslie, Phil Neville, the Wu-Tang Clan, Usher, the Sugar Puffs Monster and Daniel Day-Lewis! Welcome to Operation MindFuck!"
As Prime Minister of the Hydrans (SFC game secondary race from roughly that area) I'd increase production of M/AM and offer it to the allies at reasonable rates. (I'd want to make some latinum at the end of the day) I'd allow members of my armed forces to volunteer for service with Starfleet if the Federation was amenable, and offer my facilities for repair of badly damaged allied vessels, that might be to time costly for the allies to repair, and the refit of mothballed ships. Some technology to help with this would be appreciated. I'd use my friendship with the Gorn to ensure that at the least they don't support the Dominion, and at best they follow a similar policy to me, if not join the allies.
I would want favoured nation trading rights from the Feds and KE, and my independence guaranteed by them both. If there are undeveloped systems in their territory bordering mine, I would press for them to be ceded to me.
Now realistically without knowig that since this is Star Trek the Federation will win the Dominion should win. I would talk to the Gorn and see what their stance is. I know that the Gorn and Tholians have gone to war. I hate the Tholians. The Breen hate the Tholians. I should be friends with the Breen.
Using economic pressure I would try to get the Gorn and my own race to enter the war on the side of the Dominion.
I would need a moderization of the military with the help of the Dominion and a promiss for future trading contracts throughout the sector. This race does seem to be a race of traders not Empire builders. With a modern military I think I could convince the senate to go to war with the help of the Gorn.
Now the Gorn, myself, and Breen all with the Dominion could really bring the Tholians towards the Federation's side. Since the Gorn and myself would be mostly a secondary war front the Klingons and Federation would not spare that many ships. This would allow us to go to war with the Tholians in a surprise attack if we feel they are leaning towards the Federation but they might very well stay neutral so I would have to weigh the option carefully. If not I would try to attack the Klingon's outter limits of their territory to draw their ships away from the main front.
This might have given the Breen the upper hand in the battle that their weapon's power was disovered. This would make the Breen a very powerful ally of the Dominion and might have secured the worm hole.
IF the Tholians were going to join the Federation then there's honestly not much I and Gorn could do besides just counter balance them. However if they stay neutral and we don't attack (If we do attack we have to do a schizer(?) type plan similiar to WWI) then I think we could throw the Klingon and Federation offguard enough by forcing them into a two front war that the outcome of the whole war might be different.
