Athletes Who Bet on Themselves: The Power of Short-Term Contracts

1 June 2025

In the world of professional sports, securing a long-term contract is often seen as the ultimate goal. It provides stability, financial security, and peace of mind. But not every athlete follows this conventional path. Some choose to roll the dice, betting on their own talent and opting for short-term deals instead. These are the players who trust in their skills, their work ethic, and their ability to increase their worth over time.

This high-risk, high-reward strategy can either lead to massive paydays or backfire in spectacular fashion. Let's dive into the reasons why players take this approach, the risks involved, and the athletes who have made it work to their advantage.

Why Do Athletes Choose Short-Term Contracts?

Long-term contracts are often viewed as the safer option. They guarantee money over multiple years and provide security for an athlete's future. So why would anyone choose a short-term deal instead? The answer lies in control, flexibility, and maximizing earnings.

1. Betting on Future Performance

Some athletes believe they can improve their performance and increase their market value over time. By signing a short-term contract, they give themselves the chance to re-enter free agency sooner, unlocking bigger paydays.

2. Retaining Flexibility

Short contracts allow players to have more control over their careers. Whether it’s moving to a better team, playing in a system that fits their strengths, or choosing the right city for their lifestyle, short-term deals keep options open.

3. Capitalizing on Market Changes

The sports market is always evolving—salaries rise, team needs change, and new trends emerge. By keeping contracts short, athletes can take advantage of increasing salary caps and shifts in team dynamics that could lead to bigger contracts down the road.

Notable Athletes Who Bet on Themselves

Some of the biggest names in sports history have taken the risk of signing short-term deals, and many have been handsomely rewarded. Let's look at a few prime examples.

1. LeBron James – Master of the Short-Term Deal

LeBron James has mastered the art of betting on himself. Instead of locking into long-term contracts, he has frequently signed short deals with player options, giving him maximum financial flexibility.

After returning to the Cleveland Cavaliers in 2014, LeBron signed a series of one-year deals to maintain leverage over the team. This strategy eventually led to a three-year, $100 million contract. When LeBron later joined the Lakers, he ensured he retained control over his future earnings by keeping his options open.

2. Kevin Durant – Short Deals for Maximum Power

Kevin Durant has followed a similar path. During his time with the Golden State Warriors, he signed multiple short-term contracts to maintain financial and career flexibility. This allowed him to renegotiate annually, adjusting his salary based on market trends and team success.

By taking these short-term risks, Durant maximized his earnings while keeping control over his career moves—a bold strategy that has paid off well.

3. Joe Flacco – The Ultimate Bet on Himself

In 2012, Joe Flacco took one of the biggest risks in NFL history. The Baltimore Ravens offered him a long-term contract extension before the season started, but Flacco declined, believing he could prove his worth.

His gamble paid off in a major way. Flacco led the Ravens to a Super Bowl victory, won Super Bowl MVP, and cashed in with a six-year, $120.6 million contract, making him the highest-paid quarterback in the league at the time.

4. Kirk Cousins – Short-Term King of the NFL

Kirk Cousins has taken the power of short-term contracts to another level in the NFL. Instead of rushing into long-term deals, he played on consecutive franchise tags with Washington, making a fortune in the process.

Then, when he hit free agency in 2018, he signed a fully guaranteed three-year, $84 million deal with the Minnesota Vikings. This move secured his financial future while still allowing him to renegotiate later.

5. Aaron Judge – Turning Down a Deal to Win Big

Before the 2022 MLB season, Aaron Judge rejected a seven-year, $213.5 million contract from the New York Yankees, betting that he could raise his market value with an outstanding performance.

What happened next? Judge smashed 62 home runs, setting a new American League record. His bet on himself paid off when the Yankees rewarded him with a massive nine-year, $360 million contract.

The Risky Side of Short-Term Bets

While betting on yourself can lead to massive paychecks, it’s not always a guaranteed path to success. Athletes who take this route are exposed to several risks:

1. Injury Threats

One of the biggest dangers of short-term contracts is the risk of injury. A career-altering injury could severely impact an athlete’s earning potential.

2. Performance Decline

If an athlete underperforms during their short-term contract, their market value can plummet, leading to much smaller offers in the future.

3. Market Instability

While betting on the market can be profitable, it can also backfire. If a team's salary cap shrinks or there’s an economic downturn, players who expected bigger contracts might be left disappointed.

The Future of Short-Term Contracts in Sports

Short-term contracts are becoming increasingly popular, especially in leagues with rising salary caps and media rights deals. More athletes are realizing the power of flexibility and the potential for financial gain when they bet on themselves.

In a world where athletes are more business-savvy than ever, expect short-term contracts to remain a major trend. The key is knowing when to take the risk and when to lock in security.

Final Thoughts

Athletes who bet on themselves with short-term contracts aren’t just taking financial risks—they’re making a statement about their confidence, talent, and ability to control their own destiny. It’s a high-stakes move that can lead to career-defining paydays or costly miscalculations.

At the end of the day, sports contracts are more than just numbers on paper; they’re strategic plays in the game of business. And for those who make the right moves, the rewards can be legendary.