Of all the rogue organizations created so far in World of WarCraft I don't think any is more intriguing or complex than the Syndicate. What makes it frustrating is few people understand the depth of story behind this shadowy band. So lets take some time to look at their history, who they are today and what their ultimate goals are.
The Syndicate began as the result of the fall of the Kingdom of Alterac during the Second War. King Aiden Perenolde was a member of the Alliance of Lordaeron but he had higher aspirations than just his own small kingdom, Aiden wanted Lordaeron for himself but he had no biological claim to the throne. When the Horde began advancing Aiden and his nobles secretly agreed to assist them in exchange for clemency for their people and power. The way they did this was by granting the Horde safe passage through their territory, providing inside information, as well as diversionary tactics such as arranging a peasant revolt at Tyr's Hand, kidnapping mages from Dalaran and even arranging for pirates to attempt to assassinate Uther Lightbringer.
When King Perenolde's treachery was discovered enraged Alliance forces burned his capital to the ground. Since he WAS a king AND a member of the council they couldn't just kill him outright, such a move could cause problems in the future. Instead he was deposed and placed under house arrest at his mansion in Dandred's Fold. As for his kingdom, since all of his nobles were also suspect, rather than turning it over to one of THEM it was placed under martial law, its final fate to be determined after the Alliance finished dealing with the Horde invasion. Aiden didn't waste any time during their distraction, knowing only death awaited him if he abdicated. Since he had in his possession the Book of Medivh, (which he had ordered his soldiers to steal) he traded it to the Horde in exchange for them driving the Alliance forces from his lands.
This was the final straw for the Alliance, Aiden was declared a traitor, a price put on his head, his people were thrust from their lands, exiles left to wander following the defeat of the Horde at the end of the Second War. His former Horde "allies" offered no assistance since as far as they were concerned he had already PROVEN his untrustworthiness by coming to THEM in the first place. Besides they had enough issues of their own to deal with. Enraged, Perenolde went into hiding plotting his revenge. He began gathering up others, deposed like himself and organized raiding parties, terrorizing and stealing from the peasants still living in his former kingdom. This brought him into contact with other thieves and bandits in the area who saw the profit to be found in being part of a larger organization. By the time he had a sizable group he began to call them the Syndicate.
Opportunity arose with the Third War to cause further mischief. Learning from his earlier mistakes Perenolde didn't attempt to garner favor with the enemy rather he convinced his followers to slowly retake their former lands as well as some of those left shattered by the Plague and Scourge. Since the peasantry was already so terrorized, they could offer little resistance. By the time the Alliance could even CONSIDER dealing with him, the Syndicate were firmly entrenched, controlling a good portion of both the Alterac Mountains that had once been their home AND the Arathi Highlands of their exile.
Having retaken his kingdom as well as much of those lands once held by those he considered responsible for his downfall Perenolde could not rest. Many of those he had gathered to his banner were former nobles themselves, including his own son and daughter. None of them happily conceded to just allow Aiden to rule over them as he had originally intended. (After all it was his leadership that had gotten them all exiled in the first place.) They too desired complete control of their former lands and gathered followers to make it possible. Infighting and disputes eventually lead to Aiden's capture and imprisonment. In the end Aiden's son Aliden Perendolde managed to gain control of the loose organization through use of personal charisma and convincing the others of the dangers of dividing their combined power.
The way he did this was by allowing each Noble to control a specific section of lands along with gather their own force made up of former servitors and bandits. What has happened as a result of this is that many of the Nobles have used this opportunity to place themselves back into positions they were more accustomed. Meaning that they prefer to DIRECT their followers, bicker jealousy with one another and plot how to gain more power, wealth and prestige rather than actually going out and getting their hands dirty with the actual WORK. The instability of ruling structure and their security can be clearly seen in the fact that EACH leader has at least one body guard.
At the moment the Syndicate is a group besieged. Considered enemies by BOTH the Alliance and the Horde they have even further pressure from Ravenholdt, who have taken it as a personal vendetta to remove them once and for all. They are strongest in the areas they managed to acquire during the Third War but it should come as no surprise that ALL of these areas are little more than ruins or scattered camps from which they launch their attacks. Durnholde Keep is one of the few strong holds they have in the Hillsbrad Foothills, the majority of their forces are scattered between the Alterac Mountains and the Arathi Highlands with the former City of Stromgarde being what they consider their crown jewel and home to their most elite forces.
Why would the Horde have a problem with the Syndicate? Well Aliden Perendolde's mentor was a certain Aedelas Blackmoore. Like Blackmoore Perendolde feels that orc's are only good as brute slave labor. Further more he has in his possession a necklace that once belonged to Thrall's great friend Taretha who was decapitated for her role in aiding his escape. In addition Aliden also has a close relationship with a certain orc by the name of Nagaz. Like his father Aliden makes the mistake of thinking he can manipulate "foreign invaders" and instead is being used to further their OWN agenda. Nagaz is actually a member of the Shadow Council and is using the Syndicate's push to regain power as a way to gain a foothold in human lands. Not only the orc's have issue with the Syndicate however, certain other high ranking members have been making difficulties for the Forsaken as well. (Understandable since they are both after the same lands.) So Lady Sylvanus' people are also more than happy to see this group eliminated.
Since they ARE a faction some have asked if there is ANY way you gain reputation with them. You can actually but the maximum level you will be able to reach is neutral. (This IS a Noble lead group after all and they have no desire to have anyone else attempting to usurp their position OR authority.) The way you gain reputation is simple enough, you just have to kill Ravenholdt guards. HOWEVER, the guards drop NO loot (after all that work with locked boxes they know how to protect their stuff) and it will take approximately 2000 Ravenholdt NPC's to reach neutral. If say some rogue were to desire to gain reputation with BOTH these factions (as some prefer with the Bloodsail and the Goblin factions) it CAN be done but it will take you QUITE a while. What it would require is for the player to work on BOTH Ravenholdt and Syndicate reputation AT THE SAME TIME. So you would turn in 1 Syndicate Emblem for 100 Ravenholdt reputation then kill four Ravenholdt NPC's for 5 Syndicate reputation so that you never drop below neutral with Ravenholdt. Doing this it would take you about 3250 Emblems and 13,000 NPC's to achieve reputation with BOTH factions. As with Ravenholdt there is NO in game benefit for gaining reputation with the Syndicate, other than they won't attack you when you go by.