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Why Mike Trout Made a Big Mistake in Taking a $144.5 Million Contract From the Angels

04/07/2014 11:37 am ET | Updated Jun 07, 2014

At 22 years old, Mike Trout of the Los Angeles Angels of Anaheim is considered, if not the greatest, one of the most phenomenal players in baseball today. Well, the New Jersey native just signed a deal through 2020 worth $144.5 million. And I believe that this could be the greatest financial mistake of his life.

I understand that $144.5 million is a lot of money, a LOT of money. He can easily live a life of supreme luxury with what the Angels gave him. This is a guy who has not even made $2 million in MLB salary, so I completely understand his immediate desire for a big payday. He no longer has to worry about the ramifications of a potential career threatening injury or declining production. Mr. Trout is secure, and I applaud his conservative and responsible thinking. Yet he came up short.

Let's put Trout in a historical context here. He is really only one of a handful of players to be atop the MLB at such a young age. Had Trout not signed this extension, he would have become a free agent after the 2017 season at the age of 26. A young speedy, powerful, defensive player becoming a free agent at such a young age ... Hmmmm, does it sound familiar? Ah, yes! Alex Rodriguez!

Following the 2000 season, Rodriguez, at 25, became the most highly sought after free agent ever. He was on top of his game, and on top of baseball. In turn, he commanded a $250 million contract from the Texas Rangers. While that number is still flabbergasting in 2014, in 2000 it was unheard of, unbelievable, dumbfounding, astounding, astonishing, groundbreaking and on and on and on. To put ARod's contract in perspective, he earned $8 million more annually than the highest annual salary to that point. (The Blue Jays gave Carlos Delgado a four year deal which paid him $17 million annually.) But most significantly, Rodriguez's deal had $145 million more included than any other contract ever signed. (Kevin Brown received a seven year $105 million contract from the Los Angeles Dodgers just two years prior.)

Back to Trout ... ARod was able to command a contract unlike anything the international sports world, much less the baseball world, had ever seen. Had Trout waited and became a free agent, I honestly believe that he would have signed a contract as astounding as Rodriguez's thirteen years ago. I believe that the 26-year-old Trout, if he continued producing and stayed healthy, would have received a deal worth around ten years and $400 million.

Let's also not forget that Trout assuredly wants to take home a championship ring. Despite the fact that the Angels are among the MLB's top spenders, their production over the past couple years has been staggeringly disappointing. Even with key additions of the likes of Albert Pujols, CJ Wilson and Josh Hamilton, the Angles winning percentage is barely over .500 over the past couple of seasons. The Angels have immense talent, but it is not translating to wins. The team has tried to throw money at their problems and it's not working ... and I really do not see it working in the near future.

Furthermore, Trout would have been arbitration eligible in 2015. With his level of production he could have easily compiled $30 million to $40 million through arbitration in the seasons before his potentially 2017 free agency.

While at 29 years of age (Trout's age at the end of his extension) Trout can still sign a massive contract, I do not think it will be able to rival what he could have signed at 26. In addition, between the age of 26 and 29, he could very possibly face injury concerns and experience a regression in his abilities. Maybe he will be signing a $300 million contract at 29, or perhaps he won't be lucky and end up with something a fraction of that size. I hope for his sake, that the former comes true, but only time will tell.