Yankees fans expected the best when GM Brian Cashman announced that New York would offer Aaron Judge a contract extension prior to Opening Day. It took until the final two days before Opening Day for news to heat up, but reports began flying in about the Yankees' huge offer to the outfielder. But Judge reportedly turned town their proposal and will enter 2022 in a contract season. Aaron Judge is betting on himself.

There are cases of this strategy working out well, and others not so much. Former Mets outfielder Michael Conforto bet on himself last year and he is now sitting on the couch waiting for a contract. But for others, playing in the final season of a contract has been rather prosperous.

And therein lies the motivation for Judge's decision.

Betting on Yourself… Is it Worth it?

Aaron Judge could have gladly accepted the 7-year, $213.5 million dollar contract that the Yankees offered him. That is life-changing money and is far more than us mere mortals can ever hope to make. But when you are capable of mashing 50-plus home runs in the MLB, taking a chance could prove worthwhile.

One example of someone who earned the bag following a contract season stems from one of the most controversial players in the MLB: Trevor Bauer.

Bauer was traded from Cleveland to Cincinnati during the 2019 campaign. There were potential stirrings about an extension for Bauer with the Reds, but nothing ever came to fruition. So Bauer entered the shortened 2020 campaign in the final year of his contract. Safe to say it all worked out.

The right-hander pitched to the tune of a league-leading 1.73 ERA and struck out 100 batters in just 11 games. That 11-game span propelled the Los Angeles Dodgers to sign Bauer to a 3-year, $102 million dollar contract in free agency.

For some players, betting on yourself is worth it because their reputation is going to precede them even if they fail to post monster numbers during their contract season. Bryce Harper is the perfect example of this.

Harper spent 2012-2018 as a member of the Washington Nationals. When he became a free agent prior to 2019, Harper was coming off of a season that saw him hit just .249. His overall numbers were still solid, but 2018 was far from his best MLB season. Nonetheless, the Philadelphia Phillies inked Harper to a massive 13-year, $330 million dollar contract.

Were they paying for Harper's 2018 performance? No. The Phillies were paying for a six-time All-Star who had won the MVP in 2015 with his 42 home runs and .330/.460/.649 slash line. Philadelphia was paying for Bryce Harper's reputation.

Aaron Judge's Contract Season

So was Aaron Judge right to bet on himself? Absolutely.

The outfielder could combine Trevor Bauer and Bryce Harper's approaches to their contract seasons. Judge already has the reputation of a superstar. But he also could end up posting a tremendous individual season and increase his potential earnings.

It is realistic that Judge ends up having an MVP-esque season in his potential final go-around as a Yankee. Had he signed a contract extension in New York, Judge's motivation to perform at new heights could dwindle due to the guaranteed money. But with nothing set in stone for the future, 2022 might become the year of Aaron Judge.