Kuwaiti was a corrupt backwards fiefdom. There's no way that the regime governing Kuwait would have voluntarily joined Iraq.
That said, there are scenarios where the Kuwaiti regime gets destabilized, and absorbed or occupied by Iraq.
Or to Germany's annexation of Czechoslovakia?
IIRC there's a theory floating about that when the US Ambassador April Glaspie asked the Iraqis about the military build-up and told them that "inspired by the friendship and not by confrontation, [the US government] does not have an opinion" on the disagreement between the Iraq and Kuwait stating "we have no opinion on the Arab-Arab conflicts" that it may have been a mutual understanding. The Americans thought they were giving a green light to Iraq simply seizing the disputed border areas and negotiating the debt and oil issues from a position of strength, the Iraqis thought they were being given a green light to seize the whole country under their claim of Kuwait being the 19th province of Iraq. If the Iraqis accepted limited gains and then went after the whole place a way down the line they might be able to get away with it since no-one made a fuss the last time.Let's say then 'peacefull' in the sense nobody give a damn and no fuss, no war, so... peaceful.
In a manner similar to US annexation of Hawaii? Or to Germany's annexation of Czechoslovakia?
IIRC there's a theory floating about...
U.S. Ambassador Glaspie - I have direct instructions from President Bush to improve our relations with Iraq. We have considerable sympathy for your quest for higher oil prices, the immediate cause of your confrontation with Kuwait. (pause) As you know, I lived here for years and admire your extraordinary efforts to rebuild your country. We know you need funds. We understand that, and our opinion is that you should have the opportunity to rebuild your country. (pause) We can see that you have deployed massive numbers of troops in the south. Normally that would be none of our business, but when this happens in the context of your threat s against Kuwait, then it would be reasonable for us to be concerned. For this reason, I have received an instruction to ask you, in the spirit of friendship - not confrontation - regarding your intentions: Why are your troops massed so very close to Kuwait's borders?
Saddam Hussein - As you know, for years now I have made every effort to reach a settlement on our dispute with Kuwait. There is to be a meeting in two days; I am prepared to give negotiations only this one more brief chance. (pause) When we (the Iraqis) meet (with the Kuwaitis) and we see there is hope, then nothing will happen. But if we are unable to find a solution, then it will be natural that Iraq will not accept death.
U.S. Ambassador Glaspie - What solutions would be acceptab le?
Saddam Hussein - If we could keep the whole of the Shatt al Arab - our strategic goal in our war with Iran - we will make concessions (to the Kuwaitis). But, if we are forced to choose between keeping half of the Shatt and the whole of Iraq (i.e., in Saddam s view, including Kuwait ) then we will give up all of the Shatt to defend our claims on Kuwait to keep the whole of Iraq in the shape we wish it to be. (pause) What is the United States' opinion on this?
U.S. Ambassador Glaspie - We have no opinion on your Arab - Arab conflicts, such as your dispute with Kuwait. Secretary (of State James) Baker has directed me to emphasize the instruction, first given to Iraq in the 1960's, that the Kuwait issue is not associated with America. (Saddam smiles)
U.S. Ambassador Glaspie - Obviously, I didn't think, and nobody else did, that the Iraqis were going to take all of Kuwait.
...As you know, I lived here for years and admire your extraordinary efforts to rebuild your country...
In 1966 Glaspie entered the United States foreign service, where she became an expert on the Middle East. After postings in Kuwait, Syria, and Egypt, Glaspie was appointed ambassador to Iraq in 1989. She was the first woman to be appointed an American ambassador to an Arab country. She had a reputation as a respected Arabist, and her instructions were to broaden cultural and commercial contacts with the Iraqi regime.
...Considering how much Arabs like to talk and negotiate...
He could even have paid the Saudis off with the Neutral Zone.
I doubt the Romulans would have ever agreed to this.
.....
This might also explain why the U.S. does not topple Saddam, as the Gillespie situation exposes, the U.S. was trying to maintain a relationship with Iraq par rapport Iran. Unfortunately, Saudi pulled the "It's either us or him!" card (at this time Iraq was the sole greatest threat to the Kingdom.) The U.S. chose Saudi, and voilà.
My two cents.