Oscar’s Grind Betting System in Trading

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Written By
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Written By
Dan Buckley
Dan Buckley is an US-based trader, consultant, and part-time writer with a background in macroeconomics and mathematical finance. He trades and writes about a variety of asset classes, including equities, fixed income, commodities, currencies, and interest rates. As a writer, his goal is to explain trading and finance concepts in levels of detail that could appeal to a range of audiences, from novice traders to those with more experienced backgrounds.
Updated

Oscar’s Grind, also known as Hoyle’s Press, is a positive progression betting system sometimes applied to financial trading.

This system triess to recover losses and generate a small profit through a series of bets or trades.

 


Key Takeaways – Oscar’s Grind Betting System in Trading

  • Controlled Position Sizing
    • Oscar’s Grind focuses on increasing trade size only after a win.
    • Helps manage risk during losing streaks.
  • Profit Target Discipline
    • The system tries for small, consistent profits, resetting once a profit target is hit.
    • Promotes more disciplined trading.
  • Risk of Drawdowns
    • Prolonged losing streaks can lead to significant account drawdowns due to the incremental increase in trade size.
  • High Win Rate Dependency
    • The strategy relies on a relatively high win rate to be effective.

 

Origin and Basic Concept

The exact origin of Oscar’s Grind is unclear, but it’s believed to have been developed in the mid-20th century.

The system is named after a casino gambler called Oscar who reportedly used this method.

The basic concept involves increasing bets after losses until a profit is achieved, then resetting the bet size.

 

How Oscar’s Grind Works

Oscar’s Grind operates on a simple principle:

Increase bets gradually after losses and maintain bet size after wins until reaching a profit target.

The Four Rules of Oscar’s Grind

  1. Start with a base unit bet.
  2. After a loss, keep the bet the same.
  3. After a win, increase the bet by one unit if it wouldn’t exceed the profit target.
  4. Continue until reaching the profit target, then reset to the base unit.

Example in Casino Betting

Let’s say a player starts with a $10 base bet:

  1. Bet $10 – Loss (Total: -$10)
  2. Bet $10 – Loss (Total: -$20)
  3. Bet $10 – Win (Total: -$10)
  4. Bet $20 – Loss (Total: -$30)
  5. Bet $20 – Win (Total: -$10)
  6. Bet $30 – Win (Total: +$20)

At this point, the player has reached the profit target ($10) and resets to the base bet.

 

Applying Oscar’s Grind to Trading

While originally designed for casino games, traders have adapted Oscar’s Grind for financial markets.

Adapting the System for Trading

In trading, each “bet” becomes a trade, and wins or losses are determined by whether a trade is profitable or not.

The base unit is typically a percentage of the trading account or a fixed dollar amount.

Trading Example

Assume a trader starts with a $1000 account and a 2% base risk:

  1. Trade 1: Risk $20 – Loss (Account size: $980)
  2. Trade 2: Risk $20 – Loss (Account: $960)
  3. Trade 3: Risk $20 – Win $30 (Account: $990)
  4. Trade 4: Risk $40 – Loss (Account: $950)
  5. Trade 5: Risk $40 – Win $60 (Account: $1010)

The trader has now reached a profit and resets to the base risk.

 

Advantages of Oscar’s Grind in Trading

Oscar’s Grind offers several potential benefits when applied to trading.

Controlled Risk

The system limits the maximum bet size.

This prevents excessive risk-taking during losing streaks.

Psychological Benefits

It provides a more structured approach to position sizing, so Oscar’s Grind can help traders maintain discipline and avoid emotional decision-making.

 

Disadvantages and Risks

Despite its apparent simplicity, Oscar’s Grind has significant drawbacks when used in trading.

Limited Profit Potential

The system generally looks for small, consistent profits, potentially limiting gains during strong market moves.

Risk of Large Drawdowns

During prolonged losing streaks, the increasing position sizes can lead to large account drawdowns.

Dependency on Win Rate

Oscar’s Grind assumes a relatively high win rate to be effective, which is not always achievable in trading.

Better Suited for Trading Where Discrete Wins and Losses

It’s best for trading applications where there are discrete win and loss amounts.

An example would be binary options.

When win and loss amounts are non-range bound like in most trading pursuits – or even have minimum and maximum amounts – the applicability is more complicated.

 

Modifying Oscar’s Grind for Trading

Traders often modify the original system to better suit financial markets.

Incorporating Stop Losses

Adding stop-loss orders to each trade can help limit potential losses and protect against catastrophic drawdowns.

Traders with longer time horizons might prefer options as hedging/effective stop-out mechanisms due to markets’ tendency to gap and not honor stop-losses.

Adjusting Profit Targets

Instead of trying for a single unit profit, traders might set larger targets based on whatever their particular analytical approach to markets.

Setting Maximum Position Sizes

Establishing a cap on the maximum allowable position size can prevent overexposure during losing streaks.

Proper risk management is a big part of any approach to trading.

 

Backtesting and Forward Testing

Before implementing Oscar’s Grind in live trading, thorough testing is important.

Historical Backtesting

Running the system through historical market data can help understand its potential performance and risks.

Paper Trading

Practicing with a demo account allows traders to gain experience with the system without risking real capital.

Forward Testing

Consider using synthetic data to stress test your strategy over a wider range of outcomes and time periods than what historical data allows.

Gradual Implementation

Starting with small position sizes and gradually increasing exposure can help traders adapt to the system’s dynamics and understand whether it’s an appropriate approach for them.

 

Conclusion: Is Oscar’s Grind Suitable for Trading?

Oscar’s Grind can provide a structured approach to position sizing and risk management, but its effectiveness in trading is debatable.

The system’s origins in traditional betting games may not translate well to the complexities of financial markets – especially for trading approaches that involve discrete/non-continuous win and loss amounts.

Traders considering Oscar’s Grind should approach it with caution, thoroughly test its performance over a large enough sample size, and be prepared to make significant modifications to suit their trading style and risk tolerance.

As with any trading system, it’s important to remember that past performance doesn’t guarantee future results, and consistent profitability requires a strong understanding of markets, risk management, and trading psychology.