Sunday, December 14, 2025

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Bobby Massie Had a Unique Reply on Why He Didn’t Test Free Agency

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Football careers in the NFL don’t last long. The average length doesn’t go beyond three years. This is a big reason why so many of its athletes chase the biggest paydays they can get. There’s no telling when that career-ending injury may hit. They have to squeeze every dollar they can. However, not everybody ascribes to this line of thinking. Right tackle Bobby Massie is a great example of this.

Everybody knows that good blockers are always in high demand this day and age. Even the slightly older veteran ones. After playing out his three-year deal with the Chicago Bears, Massie became a free agent this past offseason. Considering 2018 was easily the best of his career in terms of performance, there was a good chance he’d get strong contract offers from other teams. One just has to look at what Denver gave Ja’wuan James (
four years, $51 million) for an idea.

Instead, Massie quickly signed a four-year extension with the Bears on January 26th at $32 million. Significantly less than what James got. Why would he do that? From a financial perspective, it doesn’t make a lot of sense. He could’ve at least waited until free agency got closer to see if the Bears might give him more.

The veteran told J.J. Stankevicz of NBC Sports Chicago that it wasn’t about the money anymore.

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“I made a lot of money already,” Massie said. “And what’s the point of going somewhere else, to a losing team and or even to a winning team somewhere that I don’t like or don’t feel comfortable just for a few extra dollars?

“Because really at the end of the day, how much money do you really need? You know what I mean? I’m happy here.”

Bobby Massie shows a unique perspective among modern athletes

That is a fascinating take. Massie isn’t lying when he says that too. To date, he’s made over $27 million in his NFL career. That is more than enough for him to retire and live a happy life with his family without worry. The problem isn’t what’s made. It’s what’s spent. So many athletes aren’t properly educated on how to handle their money when they get it. They often spend it lavishly, always believing there will be more. Or they dump it into bad investments.

By the sound of things, Massie has made sure to take care of what he’s done with his own finances. It would explain why he’s not as anxious to get another huge payday as most normal players would be.

There’s also the fact that Massie probably saw what the Bears were building from last year after going 12-4 and winning the division. Are a few extra dollars worth a chance to win a Super Bowl for one of the most storied organizations in football history? It’s worth the risk in his mind. That moment of selflessness allowed the Bears to keep their offensive line intact, setting the stage for what should be a fun 2019.

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