So, The War of the Ring was not kind to the Shire. With the Rangers and elves of Rivendell increasingly distracted (justifiably) by the threat of Mordor, the Shire was unprotected. This was compounded by the fact Frodo, Merry and Pippen left to join the Fellowship. Saruman meanwhile needed strategic depth. This was highlighted when he was evicted from Isengard in dramatic fashion at the end of the Two Towers. Once he was stripped of his one and only source of power, he needed to take over some alternative location. After all, he was defeated, not dead. So long as that was true, he had options and could theoretically regain power.
Meanwhile, Lotho Sackville-Baggins was looking to overcome his own problems. He was quite unpopular - nicknamed "little pimple" due to his appearance. He also disliked the main Baggins family. Apparently he resented waiting 62 years to gain control over Bag End. The fact Bilbo passed it to Frodo instead of him was particularly enraging. Keep in mind that Frodo was only 33 when he inherited it. Not to mention Frodo was not Bilbo's heir until after Frodo's parent's died. Which means that the 62 year wait Lotho waited could have legitimately be seen as costing him Bag End.
The interests of Lotho and Saruman came to overlap. Once Frodo left, Lotho managed to finally take over Bag End. Having lost it once before when a believed to be dead Baggins returned and already being unpopular, he needed to secure his position. Men from Isengard were stationed in the Shire's Southfarthing. Lotho took advantage of this to begin selling pipe weed to Isengard. He used the profits to buy more land. From there, he used these men to depose the rightful Mayor of the Shire and take the post for himself. He began taking more and more grand titles, such as "Chief Shirriff" and "The Boss".
Lets look at the main battle seen in the Shire for a second – the Battle of Bywater. The Scouring of the Shire and the resulting Battle of Bywater is actually the culmination of several trends I have seen or predict here and in several other sections. First, there is the tactics used as discussed before. Then there is the players involved that need to be examined.
Domestically you have Lotho Sackville-Baggins conducting a major land grab with the money he made selling pipe weed to Saruman. Saruman took full advantage of this, deposing his puppet, taking full control and instituting a more extreme militarization and industrialization of the Shire. This is exactly what one would expect given his outlook, interests and condition.
Then on the other hand were the hobbit leaders of the rebellion against him. Frodo was one of the major economic powers in the Shire. Pippin’s father was the Thain at the time of the Lord of the Rings and Pippin himself became Thain after. Merry became Master of Buckland. This means that on one hand you have wealthy early industrialists seeking power and resources so so they can make profit though export led growth. Then there is the effectively deposed old government in exile that led a counterrevolution due to the fact their interests were firmly connected to the status quo.
Then there is the international context. The takeover was only possible due to the withdrawal of Aragorn and the Rangers to fight in the main battles closer to Mordor. Lotho Sackville-Baggins was able to take complete control via goblins and wild men sent as reinforcements by Saruman. The result is a full client state, granting Isengard much needed breathing space and a new source of resources. Pippin also was still part of the Tower Guard – a military unit of Gondor. The King of Gondor was Aragorn, a personal friend of all four hobbits and had just laid claim for Gondor to the whole region. Merry was a knight of Rohan, a region later incorporated into Gondor – placing Merry and Pippin in the direct military service of outside powers.
Also friendly was Gandalf, the character well known for using hobbits for doing his dirty work and was not one to take lightly either. There is also the very important element that Aragorn and Gandalf were bitter enemies of Saruman’s. The result is that outside powers supported proxy forces for their own geopolitical interests in the region – be it resources, the elimination of rivals or pure territorial gain.
The Conflict
Prelude
Isengard would naturally develop plans for the area. The relative vulnerability would make it a tempting target. Especially with his orcs and wild men. These troops would not be as good in the war against Rohan. Nor would many be needed. So sending out some of his orcs from the Misty Mountains and bands of Dunlendings would be a good enough force. These would likely be the troops used to be Lotho's enforcers during his puppet days. They would probably also be the ones who murder him. More importantly, they would probably be in place at or before the attempt to conquer Rohan.
Saruman was more than happy to watch as his power grew in the Shire at the hands of Lotho. By the time he was deposed in The Two Towers, this arrangement had already entrenched all the institutional frameworks Saruman would need to assume direct control. I mean, Lotho had even set up the infrastructure for industrialization - something much needed by Saruman.
So when he did get removed, it was relatively simple just to move to the Shire with Wormtongue. Grima killed Lotho and possibly ate him. Which firmly placed Saruman at the top of the new regime built by Lotho. Because the puppet regime is much cheaper and easier to maintain, this move would not take place until after he is evicted from Isengard.
But this is where things start to get interesting. We must remember that no one interested in securing power or profit can rely on a single patron or trading partner. This means that Lotho's alliance with Isengard was a wise move. But relying on that alliance cost him his life. It seems unlikely that he would have done so in real life. But who could he have traded with and gotten support from? Bree could have provided some support. Rivendell would be somewhat useful - more power, but further away. The distance though would not be a huge problem, as the power base of his main threat (Isengard) was further still.
But there was a regional power even closer. The Blue Mountains. Were they powerful in the grand scheme of things of Middle Earth? Not really. But they would have probably be the only heavy infantry in the region. Dwarven mercenaries from the Blue Mountains probably would also be available for hire to do Lotho's dirty work. It would not be surprising if Lotho actually hired both the Ruffians of Isengard and the dwarves to serve as counterbalances to each other. He would probably trade with both. Honestly to a degree this is unintentional. The dwarves would see the rise in prosperity of the Shire and try to invest in the economic growth. When both sides have an incentive to trade with each other, it seems unlikely that it wouldn't.
The problem arises when Saruman shows up after he is evicted from Isengard. Regardless of how bad of an idea it would be, he would have no choice but to move as he did in the books. The result? He would have effectively deposed a regime with favorable trading relations with the dwarves. Said dwarves would also already have a military presence in the region. This means that they would probably attempt to exploit his vulnerable position to start the Economic Hit Man Model. Or they would go to war to support their existing trading partner.
This would have serious problems. The most obvious is that the industrialization of the Shire would be used to arm Saruman. He would probably then turn this army against the Blue Mountains first to rid himself of their control. He would also be unlikely to remain subservient to them even before hand. He would seek to violate the terms imposed, hide assets and usurp the economic power of the region for himself. This would mean that by the time the hobbits from the Fellowship show up, things with the dwarves would be hitting a crisis point already. I think the fact the Dwarves would be hesitant to threaten their investments without a ample reason, I suspect the delay would be long enough to see the hobbits return.
Then add in the elves. Remember, they too live in the area of the Blue Mountains. Not many, and mainly refugees seeking to leave Middle Earth. But in this context, it would not take much. Their strong moral opposition to all things associated with Mordor would prompt their intervention. As would concerns over their legacy. They would probably not interfere in the internal affairs of the Shire at first out of respect for international law. But when Lotho uses force to overthrow the legitimate government, that would change things. As would Saruman taking direct control himself. That would place the Shire under direct control of a hostile regime. Not to mention it being an illegitimate takeover by a person the elves would have been at war with after Helm's Deep.
One last thing would motivate the elves to jump in by the time of the Battle of Bywater. That would be the arrival of the Fellowship Hobbits. With their permission or request, the elves would have powerful cover in terms of international law. First, the family of the Thain and Master of Buckland would be in support. These same hobbits were in the service of Rohan and Gondor. We must remember that those two nations joined to become the Reunited Kingdom. This was ruled by Aragorn, who would be backing the Hobbit's claim. Both Aragorn and Theoden's family would be at war with Saruman. Most importantly, this kingdom has sovereignty over the Shire. Factor all of this together and the hobbits from the Fellowship have powerful claims to representing the legitimate authority and thus have all the power needed to invite the elves in.
Therefore, by the time of the Battle of Bywater occurs, a powerful coalition could have materialized. First, there would be the Hobbitry in Arms. Then there would be possibly returning Rangers. Next, dwarven mercenaries and troops from the Blue Mountains. Then the elves. All of this against a small militia, Saruman and Wormtogue.
The dwarves would probably send their light infantry units fitting for the decapitation strikes of the Economic Hit Man second stage. The elves from Lidon would likely send limited troops as well. They would be more technical advisers seeking to provide some sort of training. Possibly also taking some command roles. Hobbits would probably be what passes as line infantry though. The dwarves would still be the "heavy" or shock infantry even though they are light by their own cultural standards.
But Aragorn would be setting up his administration of Arnor. Which complicates matters a bit. Saruman cannot be tolerated in the area. But forces would be limited. He wouldn't have too many men to work with. Saruman would be incredibly weak too - so a full sized army would not be needed. Time is of the essence as well. The final defeat of Saruman needs to come as soon as possible. A defeat of Gondor's forces could prove devastating. So Aragorn would need a force big enough to ensure victory but still something he can get to the area fast.
So action from him would be delayed until sufficient militia units could be formed. I'm going to say that a regiment is what he allocates to this mission. When desperate for people, the German Army in World War One shortened basic training from six months to six weeks. This shorter time would be adequate for setting up a militia force. Especially one commanded by experienced veterans.
This is where the Fellowship Hobbits would be important. Given their at least symbolic political power, it would be important to have them as the nominal commanders of this regiment. This would first reinforce the dependence of the Shire's political elites on Aragorn. It would also demonstrate to the civilian Hobbits that Aragorn is interested in their traditions and in protecting them. Outside powers would naturally want to back off or support the "new" government to avoid conflict with the resurgent Gondor.
I expect this battle to take place about 2 or three months after Minas Tirith at the earliest. Possibly a year later. The time between the sacking of Isengard and Minas Tirith and the destruction of the One Ring were surprisingly short. It is entirely possible that, depending on mode of transport and how secretive he is being, Saruman might not have even made it to the Shire prior to those events. Then, the dwarves and elves would be cautious in their operations. Nor would the hobbits jump straight to revolt.
The key factor is Arnor. Gondor would need to raise the needed militia in order to get the forces needed. The problem is the manpower. Aragorn has enough for the officers, but not the men. Which then means the first step is getting the settlers in the area or recruiting from the already established refugees in the area. Then, training them would add some time.
And while all of this is happening, the hobbits, elves and dwarves would be pushed further and further towards action. Saruman would also be rearming the entire time. So I suspect that the militia formation time would be exploited to do two things. First, a diplomatic operation would be opened to create a united front against Saruman. Then, spare Rangers would be sent to spy on Saruman, sabotage his operations and do hit an run attacks. This will allow the time needed to prepare to turn into a more impressive force while denying the same chance to Saruman.
In the official version, Merry got about 200 hobbits to hide in and between buildings. Tom Cotton stood at the main intersection with the road behind him blocked. When the 20 ruffians arrived they found themselves trapped. Many tried to flee – the leader was killed while the rest surrendered.
The next day similar tactics were used in the main action. Both sides called for reinforcements, with 300 hobbits against 110 ruffians. The hobbits hid in hedges growing along high banks. Overturned carts blocked the road where the hobbits were hiding and as the ruffians marched into the ambush area another barricade was thrown up behind them. Some ruffians tried to flee the way they came but the rest attacked east. Even with their superior numbers, the hobbits on that side struggled. Reinforcements were rushed from the far side.
All of the other factors at play would suggest to me the Battle of Bywater would progress similar but with notable differences. First, the trap for the ruffians would be set up the same. The main difference would be the dwarves attacking along the road in the shock role. The elves would hide in the hedges with the hobbits providing protection to them and flanking fire.
The militia would be sent to take important targets in Hobbiton or would be kept in reserve. I suspect that the hobbits serving as the main force in the liberation of their homes would be important politically. Especially if the Fellowship Hobbits take their leadership posts. Once the main battle is won, the regiment would split up into the 8 companies. Then, one would need to go to each Farthing. One would be sent to each of the "main" cities and one each to Buckland and Tookland. These would be responsible for hunting down remaining troops loyal to Saruman or Lotho Sackville-Baggins. Then they could formally incorporate the Took and Buckland areas formally over to the Shire.
The result would be a totally lopsided victory for the Free People. The leader was again killed by Merry as the remaining ruffians were killed by archers in a wide circle that trapped them. The total was 70 killed, 12 captured and the rest routed on the ruffian side with 19 killed and 30 wounded hobbits. They then marched on Bag End, resulting in a skirmish in which Saruman and Wormtounge were both killed.
With Saruman killed, his remaining forces are driven from the Shire. The industrial development of the Shire is halted. The hobbits from the Fellowship are allowed to reside in their home. The collaborators are removed from Bag End. Merry and Pippen regain their political positions. The Shire is incorporated into the Reunited Realm under Aragorn. Aragorn forbids all but hobbits from entering the Shire. The hobbit majority border regions are incorporated into the Shire. Sam uses his Mallorn tree seed to help in the reconstruction of the Shire before running for public office. Peace is effectively secured through the final defeats of the Mordor Coalition. The Reunited Realm fully develops into a global hegemon reaching most of Middle Earth.
Possibly reconstruction assistance from the dwarves and elves would be extended. Seems unlikely that the Shire would ever be truly the same. Especially if the aid is accepted from the dwarves. This would probably mean some sort of international trade for the first time. Now, Aragorn would be keen to protect the Shire from exploitation. He did issue an edict that forbade non hobbits from entering. I would not be surprised if the export of crops to the Blue Mountains at cost until the aid is repaid.
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