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The term "bet on yourself" is often used in all facets of life, but especially in the NBA when pertaining to upcoming contracts. 

Players can sometimes forgo an earlier big paycheck to get even more money down the road. 

Other times a player can reject big money in hopes of landing more money only to come away with a lot less money. 

Dennis Schroder (Los Angeles Lakers)

The former Atlanta Hawks and Oklahoma City Thunder point guard had a solid season in Los Angeles with the Lakers putting up 15.4 PPG and 5.8 APG in 61 games (which were all starts).  

Schroeder reportedly turned down a four-year, $84 million contract extension, according to ESPN's Brian Windhorst on the Brian Windhorst & Hoop Collective Podcast back in March, h/t NBC Sports

"I believe he was offered a contract in that realm, and he said no to it," Windhorst said on his podcast back on March 30 of Schroder.

Windhorst did note that he did not know if it was fully guaranteed. 

Meanwhile, the Lakers now have Russell Westbrook as their new point guard.

ESPN's Jordan Schultz reports that Schroder has been offered $5.9 million by the Boston Celtics (see Tweet below). 

A lot less than $84 million.

Update: Schroder has agreed to a deal for $5.9 million, according to ESPN's Adrian Wojnarowski (see Tweets below).

Victor Oladipo (Indiana Pacers and Houston Rockets)

The two-time NBA All-Star was a budding superstar for the Indiana Pacers in 2018, and was on the rise once again in 2019 before a devastating injury knocked him out for over a calendar a year. 

Back on October 22, 2020, SNY's Ian Begley reported that there was talk of a 4-year, $80 million extension, and after that there was not much discussion. 

The article from Begley can be read in the hyperlink above, and an old Tweet can be seen embedded below from August 26, 2020.

After the Pacers traded Oladipo to the Houston Rockets, ESPN's Adrian Wojnarowski reported on February 28 that Oladipo turned down a 2-year, $45.2 million contract. The article from Wojnarowski can be read in the hyperlink and his Tweet can be seen below. 

The Rockets traded Oladipo to the Miami Heat, and after four-games he had a season ending injury. 

Last week Shams Charania of The Athletic reported that Oladipo is returning to Miami (see Tweet below) and ESPN's Wojnarowski reported that it was for the minimum (see Tweet below).

Oladipo will look to next off-season for a bigger deal, according to Charania. 

Oladipo and Schroder both unfortunately made the wrong decision.