Are Shagrat and Gorbag really talking about "the old days" from personal experience?

Question

In the last chapter of The Two Towers, the two orc captains, Shagrat and Gorbag discuss the current status of war and politics in Mordor. They discuss how the Nazgul are the master's preferred servants, and talk about running away to somewhere where there are no bosses (no Sauron, no Nazgul, specifically), just like in the good old days.

In reference to several questions here (regarding topics such as possible orcish immortality), people have suggested that the two captains are speaking, from personal experience, about very ancient times, in the Second Age or very early Third Age. I admit, this possibility had never really occurred to me (even though I have always thought that orcs of elvish stock ought to be authentically immortal). So, is there something in their dialogue that definitely suggests that these two orcs are thousands of years old? Or could they merely be referring to good old days only decades past, before Sauron's return to Lugburz; and references to the great siege being known to them only through history and folklore?

Answer 1

No conclusive evidence

The relevant part conversation between Shagrat and Gorbag is this:

‘They would,’ grunted Gorbag. ‘We’ll see. But anyway, if it does go well, there should be a lot more room. What d’you say? – if we get a chance, you and me’ll slip off and set up somewhere on our own with a few trusty lads, somewhere where there’s good loot nice and handy, and no big bosses.’

‘Ah!’ said Shagrat. ‘Like old times.’

_{The Lord of the Rings Book Four, Chapter 10: The Choices of Master Samwise
Page 738 (Single volume 50th Anniversary Edition)}

It is not clear whether "the old times" that Shagrat refers to are times that he himself experienced, or older times that he has heard of.

He may have been referring to the time before Sauron came back to power 68 years earlier

Even if Shagrat is speaking about his own experience, it need not have been thousands of years ago. Sauron was absent for most of the Third Age, and I assume many Orcs would have been free of "big bosses" during that period. According to The Tale of Years, it wasn't until 2951 (Third Age) that Sauron declared himself and calls his former servants to him.

2951 Sauron declares himself openly and gathers power in Mordor. He begins the rebuilding of Barad-dûr.

_{The Lord of the Rings Appendix B, Section 2: The Third Age
Page 1088 (Single volume 50th Anniversary Edition)}

If Shagrat and Gorbag had returned to Sauron's service in 2951, that would have been 68 years before the War of the Ring.

The lifespan of Orcs

The comment by AakashM links to Are Tolkien's orcs immortal?. Answers to that question by Valorum and ElendilTheTall indicate that Orcs are not immortal and do not live as long as the Edain.

They could be slain, and they were subject to disease; but apart from these ills they died and were not immortal, even according to the manner of the Quendi; indeed they appear to have been by nature short-lived compared with the span of Men of higher race, such as the Edain"

_{The History of Middle-earth Volume X, Part Five: Myths Transformed, Section 10
Page 418 (Houghton Mifflin 1993 hardback edition)}

Of course, the Edain lived much longer lives than most men, and we know that some Orcs did as well. As ElendilTheTall points out, Bolg succeeded his father, Azog when he was killed by Dain II in the battle of Nanduhirion in TA 2799. Bolg also takes part in the Battle of Five Armies TA 2941, making him at least 142 years old.

The Dragon was slain by Bard of Esgaroth, but there was battle in Dale. For the Orcs came down upon Erebor as soon as they heard of the return of the Dwarves; and they were led by Bolg, son of that Azog whom Dáin slew in his youth. In that first Battle of Dale, Thorin Oakenshield was mortally wounded; and he died and was laid in a tomb under the Mountain with the Arkenstone upon his breast.

_{The Lord of the Rings Appendix A, Section 3: Durin's Folk
Page 1079 (Single volume 50th Anniversary Edition)}

Conclusion

From this I conclude that it is certainly possible that Shagrat and Gorbag could have been living free of "big bosses" before Sauron returned to power.

Answer 2

Shagrat and Gorbag also mention "the Great Siege", presumably the siege of Barad-dur 3019 to 3026 years earlier, though it could something else like the Noldorin siege of Angband.

About SA (Second Age) 500 Sauron becomes active in Middle-earth again. Sauron begins to take control of all orc groups, ending their centuries of freedom from higher powers.

About SA 1,000 Sauron takes over Mordor, begins populating it with orcs.

In SA (Second Age) 3262 Sauron taken a prisoner to Numenor.

SA 3319 Numenor sinks, Sauron's body killed.

SA 3320 Sauron's sprit returns to Mordor and soon makes a new body.

SA 3434 to SA 3441. The Siege of Barad-dur, probably "the Great Siege" mentioned by Shagrat and Gorbag.

SA 3441. Sauron defeated and killed and his ring taken. The Second Age ends and the Third Age begins. The Kingdom of Gondor guards Morder with fortresses.

About TA (Third Age) 1050. Sauron forms a new body. All orcs and other evil creatures begin to fall more and more under Sauron's control, ending about a millennium of Orcish freedom from higher powers.

About TA 1100. The Wise realize that some dark power, probably a Nazgul, has made a stronghold at Dol Guldur in Mirkwood. Actually it is Sauron.

About TA 1300 Orcs and other evil creatures begin to multiply again. The Nazgul reappear and their chief goes to Angmar and becomes the Witch-king.

TA 1636 the Great Plague devastates Gondor.

TA 1640 Mordor is left unguarded.

TA 1975. The Witch-King of Angmar is defeated and leaves the north.

TA 1980. The Witch-king comes to Morder and gathers the Nazgul.

TA 2000-2002. The Nazgul from Morder besiege Minas Ithil, presumably with the help of Mordor Orcs. This may be "the Great Seige" mentioned by Shagrat and Gorbag. Minas Ithil becomes known as Minas Morgul.

TA 2063 to TA 2460. The Watchful Peace. Gandalf enters Dol Guldur in Mirkwood, Sauron leaves Dol guldur and hides in the East, and the Nazgul are quiet in Mordor. (But no doubt the Nazgul boss the Mordor orcs).

TA 2460. Sauron returns to Dol Guldor in Mirkwood.

TA 2850. Gandalf enters Dol Guldur in Mirkwood and discovers that Sauron has returned.

TA 2941. The Hobbit. And also the Wise drive Sauron from Dol Guldur in Mirkwood.

TA 2942. Sauron returns in secret to Mordor.

TA 2951. Sauron declares himself in Mordor and openly rebuilds his power. The Dark Tower is rebuilt. Three Nazgul are sent to rebuild Dol Guldur.

TA 3018. War of the Ring begins.

TA 3019. Presumably equivalent to SA 6460. War of the Ring continues. Shagrat and Gorbag have their conversation. This is:

68 years after Sauron openly proclaims himself.

77 years after he returns to Mordor.

1,019 years after the Nazgul have sufficient control over Mordor orcs to presumably form an army of them to besiege Minis Ithil.

1,039 years after the Witch-king comes to Mordor and gathers the nazgul, presumably bossing around the Mordor orcs.

1,719 years after orcs start multiplying again, presumably under Sauron's influence.

About 1,969 years after Sauron forms a new body and beings controlling evil creatures like orcs, ending about a millennium of orcish freedom from higher powers.

3,140 years after Sauron returns from Numenor and possibly ends a period of orcish freedom in Mordor.

And about 5,960 years since Sauron becomes active in Middle-earth again and presumably ends about 500 years of orcish independence of higher powers.

I think that it is a little presumptuous to assume that one knows which era Shagrat and Gorbag are referring to as the good old days without big bosses over the orcs. It is theoretically possible that they might be referring to the three ages when Morgoth was imprisoned in Valinor during the Elder Days.