I just finished reading the Iliad and the Odyssey. I’ve been reading them in small chunks during lunch at work. The single most surprising thing, given my prior knowledge of the two works from high school, was just how much of a jerk Odysseus was. This is all going from memory, so I’ve probably forgotten a couple Odysseus jerk moves. The following list should be fairly solid argument, however.
First, let’s talk about the Iliad. The first potential jerk move comes in chapter 10, the nighttime raid. In this chapter, Odysseus and Diomedes go out to spy on the Trojan camp. They find a Trojan spy attempting to do the same and after this guy surrenders, Odysseus and Diomedes kill the spy. To our modern sensibilities, that’s a cruel act, but because taking captives was a choice rather than a moral or ethical imperative, I’m not going to consider that a jerk move.
There is, however, a major jerk move regarding Diomedes. This isn’t actually part of the Iliad, but Diomedes and Odysseus have the task of going and grabbing a statue of Athena from Troy. As long as the statue stands, Troy will not fall. After the two Acheans grab the statue, Odysseus tries to kill Diomedes so that Odysseus could go back to the Greek camp the hero. Diomedes, being decidedly not a jerk, forces Odysseus back to the camp at swordpoint rather than killing him.
As if that weren’t enough, Odysseus was enough of a jerk that he got Telemonian Ajax to kill himself in shame. Odysseus shows remorse during the Odyssey, but save your underhanded behavior for your enemies, Odysseus.
After those two events, we go into the Odyssey, which should be subtitled, “The journey of Odysseus the jerk.” There were a number of jerk moves, but I want to limit myself to a couple of the biggest.
One of these was when the Phaecians take Odysseus back to Ithica, after handing him loads of goodies. After taking such good care of him, his first reaction is to doubt that they actually took him to the right place. I understand Odysseus is cunning and not going to be tricked (and that Athena had removed all of the important landmarks), but outright accusing them of treachery without any proof is a jerk move.
The single most egregious jerk move Odysseus made, however, was in the “trial” of his father. This was totally unnecessary. I get the trials of the swineherd and cowherd—Odysseus wasn’t sure he could trust any of his men, and if he revealed his true self to them, they might blab on accident or somebody might reveal his presence to the suitors. I follow why he didn’t reveal himself to Telemachus immediately—he wanted to test his son’s integrity and sense of honor. I get why he didn’t reveal himself to Penelope earlier—same reason, but this time regarding the maids. I even get why he didn’t want to reveal himself to his nursemaid, although his response (akin to “I’m going to kill you if you blab!”) was a jerk move too. But by the time he visits his father, all of the suitors are dead. He’s not in costume and has no reason to lie. So why does he do just that? Other than him being a jerk, I don’t know what possible gain he has from it.
As such, more than any other single character in these two works, Odysseus is a jerk.
36 Chambers - The Legendary Journeys: Execution to the max! 
Achilles was a way bigger jerk than Odysseus. This is the same guy who’s all “boo hoo hoo, you took my slave girl, so I’m going to pout in my tent and let my fellow Greeks get massacred.” He’s also all, “Hey look at me, I’m cooler than the gods, they should bow before me” which makes Hera super pissed (which, granted, doesn’t take much). In fact, scratch that: Odysseus and Achilles combined aren’t 1/10th the jerks the gods are.
Achilles had a legitimate grievance, I think. Agamemnon was trying to push his authority too far; the taking of one of his ladies was simply the move that pushed Achilles over the edge, but in the first couple of books, it’s pretty evident that Agamemnon was treating everybody like his chattel, and he did not have the binds of honor on Achilles that he had on the other Achean heroes. Now, Achilles’s reaction was a gigantic jerk move (let the Greeks die until they come begging for their savior), but a lot of the end result was because Zeus made it that way: he was going to give Achilles exactly what he asked for, several times over. In contrast, none of Odysseus’s reactions were directly as a result of one of the gods making it that way (or even really exascerbated by one of the gods, save perhaps for the Phaecian journey); rather, it was Odysseus acting as a free agent, being a jerk all on his own.
I readily concede on the gods being jerks in general. I was excluding them implicitly; we could have a whole different discussion on which of the gods was the biggest jerk (my money’s currently on Zeus), but I didn’t want to include them because of how out-of-balance the discussion would be, as you mentioned.
Here’s what separates them: Achilles knew he was being a jerk, and reveled in his jerkitude. I think Odysseus (despite being the Trojan Horse guy) is just genuinely too stupid to realize what a jerk he is.
‘Wily Odysseus’ is too stupid, Tony, to know he was being a jerk? Probably not!
I suppose I have to concede Odysseus’s general jerkitude, though I still find him incredibly likeable. He seems like he would have been a lot of fun to be around in the right circumstance. And if you find yourself trapped with the Cyclops you wouldn’t want a butch jerk like Achilles around – you want someone with their wits about them, like Odysseus.
I guess the Ancient Greeks would have been inclined to excuse a lot of this jerkitude because Odysseus was a king, and, well, kings have done much,much worse; and/or they wouldn’t even have recognised it as jerkitude anyway.
Athena herself, however, was inclined
to be charmed by her hero’s sly, crafty mind;
when he tried to fool the goddess in disguise,
she laughed and said, “Oh, you, and your cunning lies!”
I’d say Achilles was not so much a jerk as a heel.
Boo, hiss.
That was a good one.
Odysseus’s first jerk move was to bully and assault Thersites simply for pointing out the same thing that Achilles had earlier – the legitimate grievance that Kevin Feasel describes above. They’re all jerks, but Odysseus is a hyprocritical jerk.
I suppose the point of that exchange is only revered figures like Achilles have the right to criticize the king.
HA! When he got to scylla and charybdis he decided not to tell his crew about the monster on the cliff as he is afraid they would refuse to go through it. So he gears up to fend her off, to no avail of course … So when she pounces and snatches six men he says that “it was the most sickening thing he had ever saw.” The guy who saw guts being spilled for 10 years straight did not see something worse