Have you ever "regretted" the anything that happened in the universe of LotR? Have you ever fantascized about anything that would go different? Imagined an alternate course of events?

I did my share of this. And my greatest fantasy is Smaug becoming the overlord of Lake-Town. He is an intelligent, powerful and wise being, and when Bilbo meets him, through long, exhausting conversation he manages to persuade him to... share his gold with the people of Lake-Town, in an exchange of lordship, rule, being worshipped. What could tickle great dragon's pride stronger than tons of gold? Massive following. It's a long, tough road with a lot of giant bumps, but Lake-Town grows ever stronger under Smaug's rule, becoming one of the most powerful factions of Middle-earth. Bilbo settles there as the High Advisor of Smaug. The terrotories spreads, it grows from a trading town into a fully functional "nation", its now known as a Dragonlands, people of this nation use dragon symbolic on their banners, armor, the dragon influence can be seen in their culture. You catch my drift?

Very intriguing.

I love Smaug. I love him the way he is but I am oft fascinated by (interesting) evil characters, to a point that I want them to be good. Or I want to find good in them. Smaug fits that category though he turns outright evil, basically. In a similar way, I am very intrigued by Sauron in his Annatar phase, and I imagine what if he stayed good (or redeemed).

Coming back to the dragons, I really enjoyed Chrysophylax in Farmer Giles of Ham. Do you imagine the Smaug as a leader to be a bit more kindly or tolerant?

I imagine Smaug having a lot of trust and rage issues during the dawning ages of his rule, which they eventually work out, not without the help of Bilbo. I also imagine some intrigues and treacheries during the times when Smaug is widely accepted and somewhat even loved by the people of his realm. The treacheries of those who still consider him as an evil tyrant who bleeds the land instead of nurturing it, those who try to kill him and take the power. Like in the Steward's Fear

Do you think anyone potent could rise against him?

Smaug agrees to rule in exchange for worship? That doesn't sound evil at all.

Smaug agrees to rule in exchange for worship? That doesn't sound evil at all.

Thats sounds reasonable in comparsion to burning the town to the ground and killing hundreds innocents, you know?

Anyways, "worship" is the word that Bilbo used in my imagination to sugarcoat it for Smaug. What was actually happening was more like paying respect to a royal person kind of worship. Bow to the King and stuff, you know? Smaug's ego is extremely high and it needs this kind of treatment to keep him calm and clear-headed.

Do you think anyone potent could rise against him?

No, I can't see anyone.

But in Middle-earth no power is eternal. Everything diminishes. So maybe a change would eventually come. Perhaps an intervention from higher powers would be possible or necessary. And in that scenario I would love to think that Gandalf, unlike Saruman or Sauron, could be redirected to goodness again.

I wonder how things would have turned out if Saruman had not betrayed the Free Peoples. It seems like all win for the good guys with Saruman on their side, both in terms of having another ally and not having to facing a second enemy. On the other hand, things had a way of playing out just as they needed to, and I wonder if the events Saruman's betrayal set in motion were pivotal in ultimately ensuring the success of the mission to destroy the Ring.

Omg Ian! Was just about to post that!

My brother and I have created many tales and maybr even songs of Saruman turning Good again.

We even imagined ten thousand Uruk-Hai marching to the Black Gates and overthrowing Sauron.

Saruman may well be my favorite character after Gandalf and when I learned (aka read the real story/book) that Saruman died at the end, I was really sad and didn't read the book for quite some time and hated Tolkien for it. Then I came in possesion of the Extended Edition of the movie and he also dies there.... Fml..

Anyway, I always wished Saruman and Gandalf would conbine power against Sauron. Also in the end, when beaten, Saruman is sadly enough still too proud to admit defeat and come back to tthe light. The refusal of Saruman his spirit is one of the most sad things in Middle-Earth and also one of the harshest punishments. Even Feanor was accepted although kept long in the Halls of Mandos.

Saruman would be a strong ally and if he wouldn't at al have turned to evil he could've provided some great strength I always want to think. He knew more of Sauron and especially the Rings of Power then anyone else.

I can't recall the time when Saruman is deemed really evil at heart?

Then there is that too; If Saruman never turned evil, Pippin would not have been 'given' a Palantir and thus revealing secret info and Saruman would not havr give false/wrong information to Sauron and Sauron may have attacked earlier or somewhere else. Also, Saruman stalled the Ringwraiths on their way to the Shire.

But, most of all: if Saruman would not have turned evil, we probably would never have met another great, awesome character named Treebeard. Man, I love me some Ents.

Saruman deserved better and I would have loved that!

Yes, it may seem strange but there are implications that the treason of Saruman has turned out to be beneficial, especially in triggering Sauron's hasty stroke against Gondor. If he didn't betray the Free Peoples, the watchful peace might have continued longer and Sauron be both ready for the war and vigilant along his own borders. One of the reasons why the Ring is able to even enter Mordor is the actual state of war at the time -- the scuffle between Shagrat's and Gorbag's parties.

In the universe of Tolkien, which was based on his Catholic faith, evil is represented as a corruption of good (so Orcs are corrupted elves, trolls are corrupted ents). If Gandalf had taken the one ring then perhaps he would have been unstoppable, but he would have become corrupted like Gollum. Maybe he would have become something like a Balrog, not cool.

In the end evil loses, not because it is less powerful, for in fact it is more powerful, but because self-destruction is an inherent property of corruption. Infighting will always result, as it did with the orc factions, as it did between Sauron and Saruman. Even Shelob was not really slain by Sam. She killed herself by trying to crush him. To Tolkien that is always what happens, like a law of nature. Whether you agree or not, it makes the stories compelling.

The good side seems so good because they cooperate even in different roles and levels of power, submitting their personal ambition to the greater purpose. That's why Gandalf is so awesome. He has great power, but always uses it to empower others, but not in a cheesy lame way.

Whilst I completely agree with your summary, the picture painted in the Silmarillion is somewhat more colourful than that. Do not get me wrong, not being part of any church, I really enjoy how Tolkien portrays his fate. Also, the main protagonists and antagonists from the Silmarillion also fall into the above structure quite perfectly. However, there are more shady characters. Perhaps more complicated characters like Sméagol, Denethor or Boromir from LotR (those I usually enjoy reading about the most).

I also enjoy reading about Saruman, he is very interesting but I find him perhaps the most evil of all (save perhaps Morgoth himself). It makes Gandalf's phenomenal "he that breaks a thing…" all the more powerful.