For young, emerging superstars, contracts and earning power often become a combination of risk, reward and timing. For Mike Trout, the stars aligned in the form of a $144.5 million contract extension from the Los Angeles Angels, setting the once-in-a-generation all-around baseball genius up for now and later.

The news, per Alden Gonzalez of MLB.com, sent shock waves through the baseball community late on Friday evening.

With the ink still drying on Miguel Cabrera’s $248 million extension, Trout earned his own payday, re-writing the narrative and record books for players with limited service time. According to Gonzalez’s source, the deal will ensure Trout is baseball’s highest-paid player relative to service time at every juncture of the breakdown.

At first glance, Trout’s payday sets him up for life. For the average fan, the idea of making $144.5 million is ludicrous and a life-changing decision. 

Yet, by eschewing year-to-year arbitration dances with the Angels, Trout forfeited the right to hit free agency at the age of 26. Had the dynamic, two-way center fielder declined this offer, played out his initial contract and hit free agency in 2018, the richest contract in professional sports would have likely been waiting for him

Despite the allure of becoming the first $350 or $400 million athlete in history, Trout had to take this deal, even if it meant delaying that inevitable trip to the land of suitors, blank check books and impetuous owners looking to make a splash. 

Why?

Risk, reward and timing.

While any open-minded baseball observer can project what Trout can become and accomplish over the next handful of years, there’s no way of knowing what will definitely occur. With injuries or a young, unforeseen decline hit, potential earning power could be curtailed in a significant way.

Consider this: From 2005-2008—during what were his first four full big league seasonsthe American League‘s best center fielder hit 107 home runs, stole 115 bases and was worth 24.6 WAR. Over that span, only three players—Albert Pujols, Chase Utley and Alex Rodriguez—were more valuable, per Baseball-Reference (subscription required).

Looking back, it would have been easy to project Grady Sizemore for riches in free agency. That, of course, never happened. Injuries derailed what looked to be the start of a Hall of Fame career. Now, years after those star-level seasons, Sizemore is attempting to re-write his story in Boston on a $750,000 base salary.

To be fair, Sizemore wasn’t Trout. Trout owns 20.3 WAR before his age-22 season starts, while Sizemore just began to ascend and take off at the age Trout is now. Still, great young players don’t always have a linear trek to immortality. 

By signing the deal now, Trout is rewarded for what he’s done, while attempting to improve without the worry of a future deal hanging over him.  

Assuming baseball’s best player doesn’t become a “what if?” story for years to come, Trout’s career should unfold with an array of accolades and MVP awards. By the time he does hit the free-agent market at 29, unimaginable future earnings will still be possible.

By signing this deal, Trout eliminated the theoretical 12-year, $400 million deal from coming across his agent’s desk in 2018.  

That has now been replaced by two headline-making possibilities: The six-year, $144.5 million pact and a future deal—factoring in baseball’s burgeoning revenue streams and inflation—that could be worth an annual salary of $40 million. 

Essentially, Trout traded in the chance to cash in on his talent once for the opportunity to do it twice before the age of 30. Even if you believe he gave the Angels a break right now—as Dave Cameron of FanGraphs argues—riches will be there later.

The five most lucrative contracts in baseball history belong to Alex Rodriguez, Alex Rodriguez (yes, again), Cabrera, Albert Pujols and Robinson Cano. Take a look at the age each player was the season before signing their respective mega deals. 

At 29, Trout will have the chance to exceed all of those numbers.

Last, but certainly not least for a player without a career at-bat in October, is timing.

By taking the 10-year or “lifetime” pact off the table with the Angels, Trout leaves his options open for the future. Financially, his current franchise should always have the ability to pay him top dollar, but if the New Jersey native wants to flee to greener—or more successful—pastures in 2020, he can do it in his prime. 

At some point, winning becomes a major priority for each player. If Trout wins big in L.A. over the next seven seasons, there’s little reason to believe he would leave for a different market or team.

If the Angels continue to fumble their way through putting a competitive outfit on the field, big-market teams like the Yankees, Phillies, Red Sox, Mets and crosstown Dodgers would all have ample time to clear the books and allocate the necessary funds to land Trout down the line.

By signing this deal, Trout achieved the best possible outcome any young superstar could hope for: Money now, money later, and the ability to re-write his narrative before the age of 30.


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Statistics are from Baseball-Reference.com and FanGraphs unless otherwise noted. All contract figures courtesy of Cot’s Baseball Contracts. Roster projections via MLB Depth Charts.

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