The 'Sliding Doors' Bet: If You Could Know the Outcome of One Historic Bet, Which Would You Choose?

CoachTony_Bets

CoachTony_Bets

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Thought experiment: You can know the outcome of ONE bet from your past - not to change it, just to know what would've happened.

Not a bet you placed and want to know if you should've bet more. I mean a bet you DIDN'T place and want closure on what the alternate timeline looks like.

Mine: 2016, I had Michigan to win the national championship queued up at +1200. $500 bet. Finger on the button. Talked myself out of it because "betting on your alma mater is emotional, not rational."

They didn't win it obviously, but I want to know how that season would've FELT if I'd had that ticket. Would I have enjoyed it more? Less? Would it have changed my relationship with Michigan football?

Just want to know.

What's your "sliding doors" bet?
 
MadMarket
This is a great question Tony.

Mine: 2019, Chiefs to win the Super Bowl at +850 before the season. Had the analysis done, everything pointed to them, Mahomes was elite.

Decided not to bet it because "futures have too much variance."

They won. Would've been $8,500 profit.

But what I want to know isn't the money - I want to know if having that ticket would've made me watch that entire season differently. Would I have enjoyed the journey or been stressed the whole time?
 
OMG I have one!

Last year I had a 10-leg parlay typed out for like $20. It was INSANE. Random player props, game totals, everything.

Almost hit submit but my friend was like "that'll never hit" so I deleted it.

I looked later - NINE of the ten legs hit. If the last one had hit it would've paid like $18,000.

I want to know if that last leg hit!!! Not to feel bad but just to KNOW!

It haunts me lol
 
Mine's dead simple mate.

2019 Wales to win the Grand Slam before Six Nations started.

Odds were like 7/1.

Thought about putting £500 on it.

Talked myself out of it because "Wales always bottle it."

Wales won the f**king Grand Slam.

I want to know what that tournament would've felt like with that ticket in my pocket.

Every Wales match that year I was thinking "I should've bet."

Just want to know if it would've been better or worse having the money on it.
 
2018 Philadelphia Eagles to win the Super Bowl at +4000 in preseason after Wentz went down.

Everyone said they were dead. I saw value. Queued up $100.

Didn't place it because "backup QB can't win a Super Bowl."

Foles won it. $4,000 profit I didn't take.

What I want to know: would I have had the discipline to hold that ticket? Or would I have cashed out early when they were up?

The bet itself isn't what haunts me. It's wondering if I would've had the guts to let it ride.
 
2017 Leicester City to win Premier League at 5000/1 odds.

I saw the odds before season. Dismissed as lottery ticket, not serious bet.

€100 would have returned €500,000.

What I want to know: if I had placed that bet, would it have corrupted my entire systematic approach?

Would that massive windfall have made me chase similar longshots forever?

Perhaps better I didn't place it. But want certainty.
 
Early career. 2012. Had inside information on Brighton manager change before public announcement.

Could have bet heavily on Brighton results improving. Didn't, due to ethical concerns.

Brighton's form did improve dramatically. Would've made significant profit.

Want to know if crossing that ethical line would've changed trajectory. Slippery slope or one-time advantage?

Need closure on whether my ethics cost me career acceleration.
 
lads mine is different... mine is knowing what happens if i DIDNT bet...

2019 i was having a good month... up like 2 grand... had a choice... withdraw everything and take a break or keep betting...

kept betting... lost it all plus another 3 grand over next two months... spiraled from there...

i want to know what my life looks like if i withdrew that day... did i avoid the whole addiction path... am i still with my ex... do i have savings...

just want to know if that was the sliding doors moment that ruined everything...
 
yeah but its the moment... the exact moment i could see two paths... kept betting or stopped... chose wrong...
 
Conor mate that's rough.

But you don't know you chose wrong.

Other timeline might've been worse somehow.
 
Conor's answer reveals something important: these "sliding doors" moments aren't always about individual bets.

Sometimes they're about the whole trajectory of your betting life.
 
My sliding doors moment is quite different from a specific bet, it was 1987 and I had the opportunity to accept a position at a financial firm in the City doing quantitative analysis which would have paid considerably more than my university lecturer salary, I declined because I valued the academic environment and the time it gave me to pursue betting as a serious hobby, what I want to know is whether taking that City job would have led to more financial success through career advancement than I achieved through betting, Margaret and I discussed this decision extensively and she supported my choice to remain in academia but I have always wondered about that alternate path, not with regret exactly but with curiosity about the road not taken, would I have become wealthy through finance or would the demanding hours have prevented me from developing my betting methodology, I want closure on whether we made the correct choice.
 
Prof that's not really about a bet mate.

That's about your whole life path.
 
But it is related, the decision to remain in academia was partially motivated by having time to bet seriously, the alternate timeline where I took the City job is one where perhaps I never developed my betting skills at all.
 
Prof's answer and Conor's answer show that "sliding doors" moments in betting often intersect with major life decisions.
 
Princess your answer is honest though.

You want closure on a specific bet.

Some of us want closure on life paths.

Both valid.
 
Question reveals different types of regret:

Tactical regret: specific bet not placed (Princess, Taffy)
Strategic regret: systematic decision with long-term impact (Eddie, myself)
Existential regret: life path chosen (Prof, Conor)

All intersect with betting but different scales.
 
Klaus correct. My answer falls between tactical and strategic.

Ethical decision that potentially limited career earnings.
 

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