NBA players these days earn millions the moment they are drafted. While some players on expiring deals sign the first guaranteed long-term contract that becomes available, there are players who bet on themselves to try and squeeze out that extra dollar.

And there are times it does work out. However, we'll take a look at some of the guys who took the risk and missed out on the biggest payday of their careers.

5. Dennis Schröder

Dennis Schroder in a Lakers jersey with tears in his eyes.

The tales of Dennis Schröder fumbling the bag are well-documented. However, since he has signed lucrative contracts in the past and recently signed a two-year, $26 million deal with the Toronto Raptors this offseason, he'll rank No. 5 on this list. Back in the middle of the 2020-2021 season, Schroder proved to be a capable starting point guard to complement LeBron James and Anthony Davis on the Los Angeles Lakers.

He averaged 15.4 points and 5.8 assists in 61 games, leading Rob Pelinka to reportedly offer him a four-year, $84 million contract extension in the middle of the season. Schröder claimed that contract was never actually on the table.

But ESPN reported the Lakers did approach the guard about an extension at that time and that his side didn't want to talk about it until free agency. He allegedly wanted a contract worth more than $100 million. However,  Schröder still insists that he would have signed the deal with the Lakers if given the chance.

When the playoffs came around, Schröder had an abysmal two games, including a goose egg in a 30-point loss to the Phoenix Suns in Game 5. He then signed a one-year $5.9 million deal with the Celtics, only to end up back on the Lakers a season later.

4. Montrezl Harrell

Harrell's story has some similarities to his former teammate (Schröder) but with a different ending. When he approached NBA free agency in 2020, Harrell couldn't have timed it any better.

He had the best season of his career, won Sixth Man of the Year, and was entering his prime at 26 years old. A deal worth more than $15 million a season was practically a given at this point.

But Harrell did the noble thing and chose to compete for a title. He signed a two-year, $18.98 million contract with the Lakers despite getting a four-year, $80 million offer from the Charlotte Hornets. Like Schröder , Harrell would end up on the team that once offered him a huge contract only to play on a much cheaper deal.

3. Latrell Sprewell

Nobody knows for sure what Sprewell fed his family every night as a player, but it was enough for him to use it as a reason to reject a three-year, $21 million extension from the Minnesota Timberwolves in 2004. Since Sprewell had one more year left on his contract, he decided to let his game do all the talking.

However, by the next season, Sprewell regressed. Multiple teams offered him the MLE and veteran minimum deals, but Sprewell valued his pride much more. Unfortunately, that was the last time Sprewell stepped foot on the court, and Sprewell even filed for bankruptcy a few years later.

2. Nerlens Noel

You'll rarely see an athlete press charges on his agent. For defensive big man Nerlens Noel, he was left with no other choice. The Philadelphia 76ers had no plans of giving him an extension in 2017 and opted to send Noel to another team rather than get nothing in return.

He landed with the Dallas Mavericks and averaged 8.5 points, 6.8 rebounds, and 1.1 blocks in 22 games. Were those numbers impressive? Hard to tell, but to Mavs owner Mark Cuban they were.

Noel was offered a four-year $70 million extension, but he turned it down after Rich Paul convinced him he was worth much more. Noel played the next season on a qualifying offer, making only $4 million, and then he signed a two-year minimum deal with the Oklahoma City Thunder the following summer.

To this day, his total NBA career earnings don't even come close to what Cuban offered him in 2017. He sued Klutch Sports in 2021 for a breach of fiduciary duty, but a judge dismissed the lawsuit a year later. In the end, Noel agreed to pay Paul his commission for brokering a $5 million deal with the New York Knicks.

1. James Harden

James Harden in Rockets, Nets, 76ers and Clippers jerseys.

James Harden has secured the bag multiple times in his NBA career. He has made more than $330 million in salaries alone, but the reason he tops this list is because of all the money he has given up chasing for a title.

He had a chance to sign a two-year, $103 million extension with the Rockets in 2020 but chose to demand to be traded to the Nets. The extension would've made him the first player to make $50 million in a season.

A season later, Harden had another chance to be the highest-paid player in NBA history and made the same mistake. The Nets offered him a three-year, $161 million extension in 2021, but he rejected it in hopes to land a more lucrative four-year, $223 million extension in the offseason.

But since he requested a trade midseason, the money he could've made changed. If he did stick around with the Nets, Harden would've been the first player to eclipse $60 million in one season while getting paid at 37.

After the Nets traded Harden to the Sixers, he agreed to sign a two-year extension for $68.6 million after he declined a one-year option for $47.3 million. So while the money overall was more, the Sixers were paying Harden less money in the first year than he would have received if he picked up the option on the contract.

Harden agreed to do this to help the Sixers with financial flexibility as they attempted to win a title. Unfortunately, the Sixers lost to the Boston Celtics in the second round of the playoffs. This time, Harden picked up his option and then demanded to be traded. The Sixers eventually agreed to trade Harden to the Los Angeles Clippers.