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The Elder Scrolls 4 - Oblivion: Reasons why Ongar the World-Weary won't trade anymore
Ongar the World-Weary saying he needs a nap
There are good reasons Ongar the World-Weary's won't buy or sell anything
Sometimes Ongar the World-Weary doesn't want to buy anymore. This is actually a common occurrence for many people. There are really just two reasons Ongar won't trade anymore: the wrong time or place, and issues with the Thieves Guild itself.
Reason #1 - wrong time or place
Ongar only sells when he is in Olav's Tap and Tack; however, the most common complaint about not being able to trade with Ongar happens while he's actually still inside, why could this be?
Well the answer is simple actually, once Ongar decides he's going to leave for his afternoon lunch he won't trade even if he's still on his way out the door. Sometimes Ongar will decide he's going to leave (stop trading) but just sit there for another thirty minutes or more before heading out, so don't get confused on that.
The best way to get Ongar back on track is to wait or sleep until after midnight, he's always available for barter late at night; go figure, the thief is a night owl too.
Reason #2 - Thieves guild issues
The other main reason Ongar might not trade is if you get kicked out of the thieves guild, which sometimes can happen without players even being aware; although, most of the time the game will pop up a dialog box telling you that you were expelled for whichever reason.
The easiest way people get kicked out of the thieves' guild is by either getting caught stealing from a fellow thieves guild member, or by attacking/killing a fellow thieves guild member. These aren't the only reasons however, another easy way to get kicked out is getting caught stealing from one of the peasants in the Waterfront District of the Imperial City. These individuals are under personal protection of the Grey Fox himself; so in other words, don't steal from the waterfront, they're all impoverished anyway.
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Other explanations and facts about Ongar the World-Weary
Other than what's stated above, there are some more obvious reasons that aren't worth mentioning in a serious manor. One of these is that, obviously, if you kill Ongar the World-Weary, well, he just won't be able to trade anymore, which is to be expected.
As for interesting facts, if you follow Ongar around all evening you might be lucky enough to witness him go into sneak mode in order to steal some food. If you're even luckier you may just witness him get caught by the guards while he's at it too.
Also, don't forget about Ongar's lock picks. He always keeps a supply of 100 lock picks on hand for you to buy at 6 gold a piece. If you buy them all he should restock in a day or two, so check back often to keep your lock pick supply up.
The last interesting fact about Ongar is that you can actually steal from Ongar and then sell him the stolen goods. This one comes from personal experience, if you break into Ongar's house while he's not home, steal everything without getting caught, and then go back to Ongar, he'll actually buy it all from you and be none the wiser.
Ongar the World Weary isn't happy, even after trading
Ongar wasn't always so World-Weary
Ongar wasn't always so world-weary, he used to be quite the adventurer in his earlier days. When first talking to Ongar, before entering the thieves guild, he says the following: "Ongar the World-Weary, they call me. I've been everywhere, and done everything. Now I'm settled down for a good long rest." From the sounds of it he was quite the unsavory character in his past. It's unfair to Ongar to assume anything, but if I didn't know better I would say he was quite the skooma abuser in his earlier days, which would also explain his apathy towards life.
Maybe someday Ongar will regain his enthusiasm for life, but chances are he'll be apathetic until the day he dies. Ongar's quite the world-weary thief, but it's that un-enthusiastic characteristic that makes Ongar live on as an infamous legend in the hearts and minds of all who meet him.