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Fortune Favors The Bold

Summary:

(SBR AU) You are part of the Steel Ball Run Race and your involvement will change the fates of some characters.

Notes:

I loved reading SBR and sadly there are not that many Diego fics out there, so I challenged myself to write this to get better and provide some content for my fellow Diego lovers.

For reasons you will see when you start reading, I decided to give the reader's mother a fixed maiden name and her own family name is also given. I hope this does not ruin the immersion, I felt it was better this way.

This is my first work in English and I hope it is good to read.

Lastly, I want to thank MistressAkira for helping me with beta-reading!

Chapter 1: Prologue

Chapter Text

Whipple Estate Engulfed in Mysterious Smoke- Only Daughter of the House Disappears!
San Marcos. Early in the morning of September 23rd, 1890, residents of the Whipple estate awoke to the smell of smoke. The local fire department dispatched officers who arrived on scene to find no evidence of fire nor of any perpetrator, but in a twisted turn of events, were shaken to discover that the sole daughter of Lord Whipple had disappeared into thin air during the chaos. Authorities are currently investigating the case, but at present it is presumed the smoke was utilized as a diversion to kidnap the family’s daughter. As of yet, no ransom letter from the supposed kidnapper has been received.

***
“Here's your identification number card and memoration badge, Miss. Take good care of it and remember to be in time. Tomorrow, 10 am, at the beach!“

With those cheerful words, the man behind the counter hands you the items, and you accept them, steady hands and calm demeanor belying a nervousness you hope isn’t as apparent to everyone else as it feels to you. You were going through with your plan and now there would be nothing to stop you.

Getting a bit lightheaded, you leave the registration building and go to see your horse. Mellon Collie awaits you in her stable, soft eyes finding yours as you approach. Seeing her always puts you at ease and gives you the determination you needed, and the moment you see her red mane you let go of that deep breath you've been holding for some time.

You draw closer, whistling her favorite tune. Mellon Collie leans into your touch as you rub her neck just behind the ear she likes. You stroke her for sometime, until you feel she is satisfied, and you yourself have finally started to calm down.

“Tomorrow is our big day. We'll show everyone what we're capable of…” You say out loud, swinging a leg over to mount your horse and sliding comfortably into her well worn seat.“And I hope father is watching,“

You angle her to the door, and urge her to a quick trot, out into the sun. Unaware of the curious eyes that have been watching your interaction with your horse since you walked in.

***

You were laying on your bed at the inn, staring at the dirty gray wall- your only companion this evening as you struggle to sleep. Adrenaline still holds you in its throes, rushing through your body, stirring up your thoughts and anxieties.

Tomorrow would be the start of the Steel Ball Run Race and you will be part of it. Famous jockeys the world over will be your competition, a daunting fact, but you were never one to give up so easily. Above all you just wanted to prove yourself and make it through to the last stage. Thinking logically, your chances for placement were not the best, but also not the worst. You've been riding since your childhood, recreationally too, just not competitively, and perhaps more leveling, this race would also be a test of endurance and survival. You've had lots of time to prepare yourself by reading and studying everything about the climate, the geography, and surviving in the wild.

Going through all you've learned in your mind finally gives you the ease of which to drift off, a dreamless sleep that will feel way too short upon waking.

***
Ten minutes. It was only ten more minutes left until the start of the race, and the beach was filled to the brim with contestants. It was beyond your wildest dreams to see this many people gathered at one place.

When the announcement to enter the starting grids comes, you feel your blood rushing in your ears, but steel yourself and steer Mellon Collie to your starting grid. Once you reach it, you take a moment to take a look at all the neighboring riders and you see you recognize some of the more famous jockeys nearby.

You recognized the man named Mountain Tim from doing your research before, and even the once famous Johnny Joestar, but your eyes quickly fixed upon the British jockey Diego 'Dio' Brando. Your family used to live in Britain before moving to the USA, which made you feel an odd connection to the man, despite never meeting him before and only reading about him from time to time, since your father would not allow you to watch the races.

The announcement that there were only two minutes left until the race starts snaps you out of your thoughts and you chide yourself for losing your focus like that.

You could feel some of the nearby riders looking at you with derision and it doesn’t phase you. From the moment you signed the registration papers you were prepared for similar reactions, and besides you've seen worse. You done worse. You’ve seen reactions to worse.

Confidently, you straighten your back and hold your head high, eyes focused on the path ahead of you. The countdown has started. With every beat closer to the start, your grip on the reigns tightens. It's now or never.

You take one last breath to ready yourself, before the fireworks go off and everyone roars to life. What followed was immediate chaos but you wouldn't let yourself get disheartened that easily.

You had to prove your honor.