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Tear Jerker: The Life and Times of Scrooge McDuck
Scrooge and Goldie all the way. Because of just one well placed icicle from a fire hose, Scrooge misses his opportunity to make up with her, and later on throws away a letter she sends him, thinking it'll just be more harsh words, while Goldie strongly implies it involved a romantic request for him to return to her. Then when Scrooge makes a last trip to Dawson (which is hinted there but much more confirmed in later stories) with the intention to propose to Goldie, he loses his sleigh in a blizzard and nearly dies, ultimately causing him to change his mind and from that point on give his heart to nothing but money. From then on it would take 50 years before they met again, Goldie at her old age being more open with her still existing feelings, down right telling Scrooge at one point she's still waiting for him (in "A Little Something Special"). Scrooge on the other hand, while clearly still having feelings for her as well, remains firmly in his "money is my only love" policy (although it is implied in the story The Quest For Kalevala — which is not part of this comic book — that he might return to her).
On a bittersweet note however, Goldie does receive Scrooge's letter with his supposed proposal in "The Last Sled to Dawson", and, while keeping it to herself, informs Huey, Dewey and Louie how "Even if your uncle hadn't become rich, he would still have been a great man."
The complete and utter Downer Ending to the series, at least until the Time Skip. Sure, Scrooge reaches his life-long goal of becoming the richest man in the world, but at the same time he completely forsakes his family and has a reaction leaning more towards Laughing Mad than genuine happiness. His family leaves with a broken view on him, and we're then treated to the said time skip of 17 years in which 5 of them Scrooge lives in complete solitude within his mansion. When an adult Donald and his nephews are introduced to him, the previous Badass everyone's come to love has been reduced to a tired old man, needing a cane to walk, barely being able to stand up straight no more, all his previous spirit and passion completely vanished. Thankfully however, a new generation of Beagle Boys appear, and, after a hazardous chase to retrieve stolen money from them along with his nephews, Scrooge has an Adrenaline Makeover, realizing that "my greatest adventures are yet to come!" reviving his spirit completely and turning him into the Scrooge McDuck of today.
The scene where Scrooge visits the grave of his mother (chapter 9).
And a lot earlier than that: The ending of The Billionaire of Dismal Downs... Rest in peace, Fergus McDuck.