I don't like Jake Sisko. As many have mentioned, the writers seemed to have gone out of their way to make him a lazy, obnoxious and entitled jerk. And here we see the obnoxious and entitled sides in full force.
All of the DS9 lead staff are down in the dumps. Things with the Dominion aren't going well and almost daily, they hear of another ship either gone missing or lost in battle with the Jem Ha'dar. And Sisko is no exception to the bad feels, which is completely understandable.
Enter Quark, he tells Nog and Jake about an upcoming auction, which just happens to have a mint condition Willie Mays baseball card. Jake decides he has to have it, although he has no money and and no way to get any, unless he guilt-trips Nog into giving him his.
Well he succeeds in shaming Nog into giving up his fortune, but it turns out not to be near enough to buy the card. A Dr Giger bids twice what they even have to bid with. From that point on, Jake becomes even more insufferable, obnoxious and downright an a$$ to his so-called friend.
He would risk Nog's entire career with Starfleet, everything he's worked so hard for, and doesn't give it a second thought. He's obsessed with getting this card, thru Nog's hard work/money, whatever means, and then having Nog give it to him so he can present it to his dad. What a guy! The entitlement is thick as molasses in this one.
So, they meet with Dr Giger, who bought the baseball card, and he tells them it isn't for sale, but he'll trade them for it. If they come up with a list of his demands, he'll give them the card. So they set about getting the items: trading for some, working for some and stealing some.
At one point, Nog has agreed to filter out distortions from all of Worf's Klingon operas, and he's working on that in their apartment. At the same time, Jake decides he needs to "work" so he pitches a fit and then snatches away the remote and turns off the opera. Now, don't forget, Nog is doing all this for him, selfish little creep that he is.
So they finally gather everything and take the final items to Dr Giger's quarters, but he's long gone. So they go to report this to Odo, and find out they've been interfering with an official investigation into this guy. Of course, Nog is very worried, but Jake ignores this completely and is totally disinterested.
Instead he's now laser focused on yet another stupid idea. He's decided the vedek who was bidding against them in the auction, was in cahoots with Winn, and because Winn was so angry about losing the auction, she kidnapped Dr Giger to get it. Jake is an absolute moron! And of course, he plans to get Nog into even more trouble without care or concern, even tho he's supposedly his best (and only) friend.
So Jake marches to Winn's quarters and straight up accuses her of stealing and kidnapping. Which of course; lands them straight into Sisko's office where they get their butts chewed out, and Jake lies to his father, potentially causing Nog even more problems, because he doesn't want him to know about the baseball card.
So Jake and Nog leave Sisko's office and are immediately transported aboard a Jem Ha'dar ship and confronted by Weyoun for whatever they have to do with Dr Giger. They try telling Weyoun the truth that they were just after the card, but Weyoun doesn't seem to believe them. So brain surgeon Jake, tells him that he and Nog are with Starfleet Intelligence and they're after this Dr Giger because the card has something to do with some convoluted time travel plot...it's totally ignorant.
Weyoun obviously knows it's bullchit, and let's them leave, giving Jake his prize for daddy on the way out. They present it to Sisko, and he gets a big hug, and not even a hint of a whisper of thanks for Nog. So all is well that ends well, and no one calls Jake out for being the complete creep that he is.
The secondary plot involves Kai Winn boarding the station to meet with Dominion representative Weyoun. Now, I love Jeffrey Combs. To me he is hands-down the best visiting cast member, no matter what part he is playing. He does them all with relish and zeal, and superior acting skill.
My problem with this plot is, why the hell is Kai Winn meeting with a Dominion rep anyway?! Wouldn't that be something First Minister Shakaar would be responsible for? He handles the business side of Bajor, Winn handles the religious side. At most, they might meet with Weyoun together, but for Winn to be the only one, makes zero sense to me. Maybe they've mentioned it and I somehow missed it even on my rewatches.
All in all, this episode for me is a throw away. Unfortunately I'm a completionist and can't skip an episode when I'm doing a watch-thru.
On a side-note: if Winn ever reached up and grabbed my ear like she does everyone else, she'd pull back a bloody stump. I hate that pretentious, condescending chit. She's reading someone's pagh...ha! She doesn't have the spirituality of a coconut. That is one evil beyotch.
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