There is a well known question on verse Genesis 24:39.
Eliezer Abraham's servant goes to Abraham's family to find a wife for Isaac. As he tells the family how he met Rebecca he says the following:
And I said to my master: Perhaps (Hebrew "uly) the woman will not come back with me?'
Rashi says: The word 'Perhaps' (in Hebrew 'uly') is written without a 'vav'. Eliezer had a daughter and was looking for an excuse so Abraham would say to him and turn to him to have his daughter (marry Isaac). (But) Abraham said to him: "My son is blessed and you are cursed and one who is cursed cannot cleave to one who is blessed!"
However, the same word is found in the original telling of the story, Genesis 24:5. There it says "And the servant said to him: Perhaps(uly) the woman will not want to come back with me to this land," etc. In that verse the Hebrew word "ulie" is written full, with the 'vav' - so the reading 'ailie' cannot be read into it there. Nevertheless, this is the original place and Rashi does not say anything. If Eliezer's intention was to indicate to Avraham, "Hey, I also have a daughter - why not her?", this is where Rashi should have made his comment. The question is an early one, we find Minchas Shai asking it and referring us to Gur Arye. Gur Arye says that Eliezer made his desire explicit for Lavan and Besuel so us to be able to share with them Avraham's answer to him - that he is of blessed stock. Devek Tov answers that Eliezer did was inhibited from saying it clearly to Avraham but not to Lavan and Besuel.
An answer suggested by Reb Mendel of Kutzk, (1787-1859) is that when a person is entangled in his own personal desires he cannot see them or be aware of them - if he were aware, his conscious awareness would alert him to the unreasonableness of the thought and he would drop it. Therefore it must remain hidden from his awareness. But once the person is not in the situation he has some distance from it, and then he allows himself to be aware of his inner desire. So when Eliezer was talking directly to Abraham he was in the throes of his desire, it was thus out of his awareness and the verse does not hint at it. But when he spoke later to Rebecca's family he had the distance which allowed him to be aware of his personal involvement. So it was only there that the verse hinted at it.
Another Answer suggested by the Magid of Dubna, (1740-1804). by way of parable, also offers an insight into how people work. Since Eliezer had his high hopes for his daughter to marry Isaac, his doubts about the suitability of Rebecca for Isaac were then subtly conveyed in the way he spoke to the family. This would make the family wonder if it was a good idea to have their daughter marry Isaac. The Torah expresses Eliezer's desires here (and not earlier) by the spelling of the word 'ulie' making it look like "eilaii"(to me.) because it was only in the conversation with Rebecca's family that it would have the desired effect.
My discomfort with these two latter answers is that they minimize the stature of Eleiezer, of whom Bareishis Rabba(Ch. 59) says: :"Hashem blessed Avraham with everything - that he ruled over his inclination.....His servant(Eliezer) who ruled overything everything of his: that he ruled over (his ) inclination". Surely a person who rules over his evil inclination would be aware and rise to the challenge of controlling unworthy thoughts. Chazal compare Eliezer to Avraham;s self-mastery; would not such a person recognize his negiyos and act honorably and with integrity. I am aware that a very different view of Eliezer is presented in Pirke D'Rabbi Eliezer 16:3, where he was initially Nimrod's slave, was suspected of immoral behavior with Rivka and is identified with Og, King of Bashan. Nevertheless, Rashi is based on GenesisRabba with its positive view of Elezer.
There are many answers to this question. Based on an understanding of the science of negotiation, I offer another one.
The source for Rashi is Bareishis Rabba 59:9. There Eliezer is called Canaanite, after Hoshea 12:8: "Cannaanite, in his hands scales of deceit". Eliezer is said to have attempted to deceive Avraham because he wanted to bring about that his own daughter marry Yitzhak.
Now, in what way was Damascean(from Damascus) Eliezer( Gen. 15:2), a Canaanite? He must have been from Aram as it says, "for the head of Aram is Damascus, and the head of Damascus is Rezin"(Ishaya 17:1).
You can say that Rashi's reference to Eliezer being cursed refers to him being a slave, and being a slave is a cursed state, for Canaan was cursed with being a slave to his brothers. A slave of any nationality is, in a sense, a Canaanite. However, there may be another, somewhat more subtle connection to Noah's curse. Netsiv to Genesis 24:3 and especially to 12:6 shares with us a very important point. He posits that descendants of Shem or another nation who lived in the Land of Canaan, for Canaan at that time was conquering the Land from the sons of Shem. As such, anyone who lived in that land was culturally a Canaanite, even if her family initally came from a different stock. It's like a resident of Meah Shaarim who would under no circumstance marry an American, no matter how frum he may be. Being an American indelibly taints a prospective suitor, even if it not clearly recognizable at the time.
But let's get back to the term Canaanite. In Tanach, Canaanites are merchants and traders. Presumably, Israelites were farmers, who toiled their land and surviving Canaanites, who was dispossessed by them and had no land of their own, became itinerant mechants. Even at earlier times, Yehuda married the daughter of a Cannanite man, read trader. As we said, Canaanites were just then conquering and spreading through the Land. In areas they did not conquer, they traded, and so Yehuda's father-in-law was caleld a canaanite withotu actually being one.
Here are some proof verses:
Wail, O inhabitants of the Mortar, For all the people of Canaan will be silenced; All who weigh out silver will be cut off(Zephania 11:1).
"Cannaanite, in his hands scales of deceit"(Hoshea 12:8)
Who hath taken this counsel against Tyre, that was formerly crowned, whose Cannanites were princes, and her traders the nobles of the earth?(Ishaya 23:8).
And , of course, a posuk we all know and love.
She made fine linen, and sold it; and gavegirdle unto the Canaanite(Mishle 32).
So, Eliezer was a mmmerchant, and what do merchants do? They bargain!
Eliezer was in negotiations for Rivka. A task that the negotiator must perform is to assess whether there is genuine desire to make a deal and the other side is being difficult to extract concessions, or is there no desire to achieve an agreement and the negotiations are merely for show. In the former, a wise negotiator may deliberately show frustration or threaten to stop trying to bring the two parties together. He may even hint that his own interests are not in working hard to make a deal come together but, being an honorable man, he would try, but not very hard.
This is what Elezer did. By hinting to Lavan and Besuel that he would rather marry his own daughter to Yitzhak, which he had no intention of doing, he prodded them to immediately agree to the shidduch. This is why Lavan is so uncharacteristically pliable at this time. He doesn't even ask for a dowry, very unusual for him, as we know of him in connection to Yakov. This is why Rashi brings it only in the second retelling of the conversation with Avraham - because it was a negotiating ploy and only applied that time.
However, though well intentioned and even helpful, this was a misleading act. This is why Chazal faulted Eliezer for it and called him a Canaanite, meaning a merchant. Avraham himself would never engage in such tactics, but Eliezer did.