World's Richest Man: I Leaped Across Time

She was sixteen years old or so, with dark hair and wearing a pair of bell-bottom jeans and a fashionable sweater.

"What are you looking at?" she asked me degradingly, with sibling contempt.

Without thinking, I stepped forward and threw my arms around her, pulling her into a tight hug. Her body stiffened in alarm and confusion as I did this, her hands hovering awkwardly at her sides.

"What the fuck is your problem, dickhead?" She barked, pushing me away.

I missed Sydney.

"It's good to see you, Sydney."

She looked at my face, disgust evident in her eyes. "Are you crying?" she asked incredulously. "What kind of sick shit is this?"

"Stop cussing, Sydney!" Jessica, my mother, reprimanded sharply.

Sydney rolled her eyes. "It's not my fault Jack's acting weird," she retorted.

Mother sighed, "Ignore him, Sydney. He's just trying to get a reaction out of you."

I stepped into the kitchen, where the dinner table was set. I noticed a calendar hanging next to the fridge. I remembered that my mother always marked important dates meticulously.

I walked up to it and saw that May 1st was ticked off.

Turning around, I found my father and sister already seated at the table. My mother was carrying a dish to the table, though it did not look so good.

Cooking wasn't her strong suit. She wasn't an at-home-mother so she hadn't had the time to practice until later in her life.

I was also so used to eating in restaurants...

I sat down and ate. I wasn't about to throw a tantrum.

"Is it the second of May already?" I said casually.

"It's the third," my father replied nonchalantly, biting into what looked like a rather blunt-looking pork rib.

May 3rd, 2002. This was the day that I returned to.

"I want to visit Grandpa today." I announced.

She gave me a strange look. "What for? You're not about to tell me that you miss him... and it's late, Jack."

"It's going to be sunny for a few more hours."

"Don't you have any tests tomorrow?" my dad interjected.

"No," I replied confidently, though in truth, I had no idea. But there was something important I needed to discuss with my grandfather.

My birthday was on June 12th, which meant I couldn't open a broker account yet. Plus, without a car, my options for making money were limited.

Luckily, I knew of another way to capitalize on my knowledge of the future.

After dinner, I grabbed my backpack and made my way to my room.

Opening the door, I stepped into my old bedroom. It was cramped, less than 6 square meters—with just enough room for a bed, a desk, a wardrobe, and posters of NFL and NBA players.

I used to be a huge fan of American football and basketball back then. Over time, my interest had waned, or perhaps I simply couldn't find the time to indulge in them anymore.

I set my backpack down and opened my dresser. I dug through it, marveling over my high school tastes. There were a couple of ripped jeans and a pair of 501 jeans that had seen better days.

Graphic T-shirts with band logos and a couple of oversized hoodies. Thankfully, tucked away, I found a simple white T-shirt as well as a pair of black cargo shorts.

Alongside those, I took out a pair of worn-out Converse sneakers and a baseball cap with the logo of a local sports team.

I changed into these clothes and stood in front of the mirror, I adjusted my outfit and checked my reflection. This should still be in fashion, and at least it was simple.

There was nothing better than a nicely fitted black suit, though.

As I got dressed, I thought about one of my regrets—I had stopped exercising during my university years. I wasn't ripped, but I used to do some body-weight exercises regularly.

Running, however, wasn't something I had ever gotten into, so maybe it was time to give it a shot.

Before heading out, I remembered something. I walked over to my drawer and opened it, reaching for an old book that had been lying there for years. Flipping through the pages, I found a few banknotes tucked inside.

Somehow, I still remembered where I had hidden them. Maybe it was because I had always been so focused on money my whole life.

There were two $100 bills and one $50 bill.

Smiling to myself, I took out $150 and slipped the bills into my pocket.

Leaving my room, I headed out of the house, only to be stopped by my father.

"Just make sure you're back before it gets dangerous," he cautioned.

"Don't worry. I'll be careful," I reassured him before heading out.

He had a point. While our neighborhood was relatively safe, our town had its rough areas. I think around this time there had been a shooting in a more remote district.

It wasn't uncommon to hear about incidents where someone got beat up or ganged up on. The police often mentioned they couldn't be everywhere at once and some people were just prone to violence when boredom struck.

Life had taught me a thing or two about hand-to-hand fighting. The most important thing I'd learned was that, while getting hit by a fist was painful, it wasn't 'that' painful.

Later on in life, I even took some lessons in self-defence. The Johnson family assigned a bodyguard to me, but you never know.

I walked only a few meters out of my house when I came to a dead stop. Parked next door was a red Ford F-150, and standing by the car was Chloe Flynn.

Chloe and I had been friends and neighbors since we were five. She looked good wearing a red baseball cap, her long, silky brown hair sticking out of the back in a ponytail.

Chloe wasn't a classic beauty because her nose was slightly too large for her face, but she had a healthy girl-next-door look. She was my age, so we used to walk together to middle school.

Chloe was a bit of a tomboy, loving to play basketball, but when high school came around, she grew up and her body developed.

Seeing the flare in her hips was probably too much for a teenage boy and we started to separate a bit.

As I jogged by her, I called out, "Hey, Chloe!"

She glanced up, a bit surprised. "Hey..." she responded, adjusting her red baseball cap.

My grandfather lived just a street away and I decided to run all the way. He was a great man who really loved sports. He would often take me to basketball matches.

The important thing was that not only did he love to watch them, but he also had a penchant for betting on them.

When I arrived at his house, I saw him sitting on the porch with a tobacco pipe in his hand. He had glasses on and his head was full of grey hair, but despite being 65 years old, he wasn't shorter than me.

I smiled when I saw him.

Grandma had died in the year 2000, and he was alone now.

"Hey, Grandpa!" I called out as I approached.

He looked up and smiled back. "Hey there, sport! How are you doing?"

"I'm good," I replied, taking a seat next to him. "Just got back from a school trip."

We briefly spoke about my future life choices and my results at school.

I must sadly say that I lied a bit to him.

To justify myself, I couldn't remember much of how I was doing back then.

"Grandpa, I have a little request," I said, shifting in my seat.

He raised an eyebrow, taking a slow drag from his pipe. I could smell the cherry tobacco.

"Oh? What is it, Jack?" he asked.

"Would you be able to make a sports bet for me?"

My grandpa often asked someone who lived in Las Vegas to bet for him. At that time, it was against the law in Florida to bet on sports. Some people would bet on websites owned by offshore companies, but my grandfather has been using this method of Las Vegas betting since the 70s.

He took another puff from his pipe, the smoke curling lazily upwards. "You want to try your hand at betting now, huh?" He mused, a twinkle in his eye.

"Yes, I've been following the games closely, and I think I have a good feel for it."

He chuckled softly. "Back in my day, we'd call it taking a chance, not betting. But I suppose the game's still the same. Well, I suppose I can help you out."

"Thanks, Grandpa." I said and I quickly stepped into the house, grabbing a scrap of paper and a pen.

I came back out and sat back down. "I should warn you though; you might not like the bet."

He chuckled again. "Well, as long as it's your money, if you lose, it'll be a lesson for you, won't it?"

I nodded and handed him the piece of paper.

He adjusted his glasses, glanced at the paper, and was quiet for a moment.

"How much are you thinking?" he asked.

"Maybe a hundred fifty bucks?"

He looked at me meaningfully, then stood up and ruffled my hair affectionately.

"Alright, I'll make the call to my guy in Vegas. Let's see if Lady Luck's on your side. Just remember, it's not about winning or losing the money. It's about understanding the game."

I was relieved that he was willing to help. "Thanks, Grandpa. I appreciate it."

He winked at me, a gesture I'd seen him do countless times, but that I have forgotten. "No worries, kiddo."

A few minutes later, before heading home, I handed the bills to my grandpa.

I needed to make some money and what better way than to gamble with no risk?

I couldn't bet on the Superbowl, although it would've been tempting.

The underdog New England Patriots defeated the Pittsburgh Steelers to reach the final and in February 2002, they won the Super Bowl against the St. Louis Rams. If I had bet on them, I could've made maybe twenty times what I gave Grandpa.

But I wasn't worried about missing out, because I had something even better.

The NBA playoffs were currently ongoing.

Sacramento Kings and Los Angeles Lakers will be the ones to enter the final. Lakers would be the ones to win with a final score of 4-3.

If all of these bets were combined, in my estimation, the cumulative odds would exceed thirty times the original bet.

I hoped that the future would be the same in this timeline.

In any case, I will find out in about a month or so.