the lord of the rings - Tolkien calls Sauron Morgoth's Greatest Servant - But does he ever really earn that with his actions?
Alright, so there is a great, incredibly well informed community here so let me ask a question that's been bothering me since I finished the Silmarillion. I'll lay out my reasoning for why it's a question as well, so bear with me.
Tolkien states
Among [Melkor's] servants that have names the greatest was that spirit whom the Eldar called Sauron, or Gorthaur the Cruel.
-The Silmarillion, p.28
What exactly does Sauron do in the Silmarillion to earn this distinction? The Dragon Glaurung is far more of a terror to Morgoth's enemies than Sauron. He annihilates whole legions of First Era elves; more or less singlehandedly breaks the siege of Angband and uses his magic stare to mind control/soul crush pretty much anybody he wants to. Not only that but he exhibits significant cunning and is a successful leader of Morgoth's forces in his own right. How is this murder-addicted hyper-dragon not number one? When Morgoth needed to kill Elves dead he went to Glaurung, handing him command in the most critical battle in the war thus far. The result was a victory so one sided and absolute that in an instant the entire dynamic of Middle-earth shifted completely.

It's also a battle where Sauron is conspicuously absent (this is a recurring theme). Not exactly what you'd expect from Morgoth's 'greatest servant'. If he was really that useful you'd think he would have had some role in a battle Morgoth had been preparing for for over 400 years.
Sauron's biggest contributions to his Master's First Age war effort were
- Hiding from the Valar...twice
- Effectively begging for mercy when unable to hide.
- Losing Tol Sirion to an overwhelming army of two people.
- Messing with the the wrong girl and getting choked out by her talking dog.

Seriously, all joking aside Sauron's first era resume is pretty bad. And let's not forget that everything past the First Age was more or less an afterthought; paling in comparison in terms of magic, power, epicness, etc.
I get that Sauron is the most 'dark-lord-like' and the heir apparent to Morgoth. The only answer I can think of is just that; Sauron is the only one who'd 'pick up the torch if Morgoth fell, whereas Glaurung would have probably just found a pile of gold under a mountain somewhere and been content. He needed direction and wouldn't be 'independently' menacing to Middle-earth in anything but a localized way (a la Smaug).
But Tolkien is talking about Sauron in the context of a servant, not based upon some hypothetical future-dark-lord skill set. I'm fairly sure the thought of being permanently defeated never entered Morgoth's mind and 'being able to take over for him' was never a looked-for qualification in subordinates. The only thing that makes Sauron special is that he seemed to be the only guy who was good enough at hiding/begging to survive Morgoth's fall.
Sauron's Dark Lord tenure wasn't exactly Hall of Fame caliber either. Nothing he ever did on his own was ultimately successful and each of his schemes backfired in some way. His plot to destroy Númenor cost him his body; and his attempt to buff himself with the One Ring ultimately led to his end as a force in Middle-earth.
So what am I missing or misinterpreting? Am I looking at this the wrong way?
TL;DR: Dragon Glaurung accomplished much more nefarious deeds than Sauron according to The Silmarillion. Doesn't make sense that Sauron is Morgoth's #2.
Answer
Who is more powerful, the President of the United States or the marine guarding him? In personal one-on-one combat I'm certain the marine would defeat the President. However, it is the President that commands the military of the United States.
Similarly, other Middle-earth creatures may have been more powerful individually (Balrog, Dragons, etc) but Sauron worked by organization, corruption, deceit, and over long periods of time.
As @DarthSatan says, without leadership Balrogs, dragons, etc. just wander off and do their own thing. Yes they are powerful, but how much damage does a Balrog do deep in the mines of Moria? How much damage does Smaug do sleeping deep under the Lonely Mountain?
Sauron not only organized the armies of evil (including the lesser ones like the Easterlings, Uruk-Hai, etc. and the greater ones), he used his knowledge and power to corrupt his opposition (Saruman & the Palantír), and sap it of strength (Lord Denethor & the Palantír).
Even his magic items (without direction) were capable of corrupting and turning beings like Smeagol to evil and nearly turned Boromir too. Brief interaction with them posed severe tests of will to others like Faramir & Galadriel.
Although not covered in The Hobbit & The Lord of the Rings, Sauron also caused the fall of Númenor. At their heights, the men of Númenor by some measures were more powerful than the Elves. It was the Men of Númenor who created the walls and tower of Orthanc which, at the time of the Third Age, no power on Middle Earth had the ability to bring down - not even the Ents.
Sauron caused the fall of Númenor not through direct firepower but by persuasion, lies, deceit. He corrupted the men of Númenor and had them use their power against Valar.
Prompted by Sauron and fearing old age and death, Ar-Pharazôn built a great armada and set sail into the West to make war upon the Valar and seize the Undying Lands, and by so doing achieve immortality. Sauron remained behind. This force was quoted by Tolkien as the 'greatest force ever assembled on Arda'.
As described in the History of Númenor.
Sauron's greatness is similar to that of Gandalf's. Their's is not brute physical or magical power like that of the Queen chess piece, it is more like that of the chess master - moving the pieces around.
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