Here’s how much Mike Trout could have made in free agency this winter

Jeff Passan
MLB columnist

Mike Trout could have been a free agent this winter. Three years ago, he signed a $144.5 million contract extension that will keep him with the Los Angeles Angels through the 2020 season and ensure future generations of Trouts drive only the loveliest flying cars. In doing so, he kept baseball from the frenzy of all free agent frenzies.

Still, this is MLB, king of hypothetical sports, and a particularly inquisitive front-office type recently posed a question to which he didn’t know the answer: What would this winter look like had Trout not accepted the Angels’ deal? And what sort of contract would a 26-year-old Mike Trout land as an unrestricted free agent?

The answers: Insane and insane, respectively. To figure out just how outlandish, Yahoo Sports asked a wide swath of GMs, assistant GMs, scouts, agents and sundry baseball types to provide an estimate on a hypothetical Trout deal. Sixty-three people offered their opinions. The lowest dollar value was $200 million – and that was on a four-year deal. Yes: The idea of Mike Trout as a $50 million-a-year player is not at all far-fetched.

Because another two people suggested five years and $250 million would be the sweet spot while one went so far as to say the bidding would go to 10 years and $500 million. That $500 million number wasn’t the ceiling, either. One person wondered if a team might consider a 15-year, $600 million deal, which seemed absurd until one remembers that Alex Rodriguez, as a free agent at age 26, more than doubled the previous record contract in baseball when he signed for 10 years and $252 million before the 2001 season.

Back then, the game’s revenues were about $3.5 billion. Today, they’re upward of $10 billion. So a $500 million contract is not excessive – not close when compared to Giancarlo Stanton’s $325 million deal – considering that Trout would be the single greatest free agent ever, even better than A-Rod.

In his five full seasons, Trout has won a pair of MVP awards and finished second the other three times. Only Ty Cobb has more wins above replacement than Trout through his age-25 season, and Trout should pass him by season’s end. He is playing at a higher level now than ever, slashing .337/.455/.725 with 17 home runs, 11 stolen bases and a perfectly solid center field glove. He is, by all accounts, a delightful human being, an exemplary teammate, a humble person – the antithesis of A-Rod as a player.

And the age. That’s the kicker. More than ever in the post-amphetamine era, teams covet 30-and-under players. The Cubs guaranteed Jason Heyward $184 million over eight years when he hit free agency at 26. Age matters. Trout may well still get an obscene deal when he actually reaches the market at age 29 – especially with Bryce Harper and Manny Machado having set the market after the 2018 season – but being 26 would allow him the option to take a short deal or target an incredibly long one.

Mike Trout could have been a free agent this winter. He would have been a very rich man. (Amber Matsumoto/Yahoo Sports)

The risk of the shorter deal is obvious. If Trout got hurt or underperformed, he’d leave money on the table. Plenty of it potentially. And not just that: If the average annual value of his deal is somewhere in the neighborhood of $50 million, that’s the number used to calculate his luxury tax cost.

As one scout noted, that is an important point not just for hypothetical Trout but real Harper and Machado: “As good as Trout is, there’s a cap for his contract that has nothing to do with Trout. The [new collective bargaining agreement] is hard on high-dollar teams. At some point, and I’m not sure where that point is, but at some point, the cost will outweigh the return, no matter how good the player.”

Between that and human beings’ love of round numbers, it’s why the most common guess – nearly half of the 63 who responded – was a 10-year deal for $400 million. It checked off a number of boxes. The $40 million-a-year threshold. The double-digit years. The largest contract in sports history. Yes, yes, yes.

And yet one agent and one general manger landed on the same number, and considering the amount of money coursing through baseball today, the limited avenues to spend it on amateur talent and the unique opportunity to get perhaps half a decade of prime years or more, this might be closer to the actual figures were this not simply a thought exercise: 12 years, $480 million.

A 26-year-old Trout as a free agent feels like a perfect, picturesque beach house put up slightly under market to create a bidding war. If every team in baseball understands that it’s going to take 10 years and $400 million to get a seat at the table, those truly interested will begin sweetening their deals to differentiate themselves. If Albert Pujols and Robinson Cano and A-Rod can sign deals into their 40s, will a team really balk at signing Trout through age 38? Or, in the case of that 15-year deal, 41?

To add another layer to the intrigue, picture this: Mike Trout, trade candidate. The Angels are hovering around .500, and with arguably the worst farm system in baseball, they could restock themselves selling Trout as a rental. This is like baseball inception, a dream inside of a dream, but teams would be falling all over themselves right now to add the best player in baseball, even for just two months. The recruiting opportunity alone would be worth the prospect haul that few teams could even muster.

The Houston Astros? Before Carlos Correa’s injury, they were a threat to score 1,000 runs, and Trout would’ve made them scarier than they are already. The New York Yankees? They’d find room. The Chicago Cubs? They may not have the goods, but start a deal with Kyle Schwarber and maybe there’s something there.

Enough fever dreaming. This isn’t real. Neither is envisioning which team would pursue him hardest this winter. Would he go home to Philadelphia, which has next to no long-term contract commitments on its books? Would New York dazzle him? Would the Angels prey on his love of Los Angeles – or might the Dodgers sneak in and offer him the LA lifestyle in a winning wrapper? It’s truly fascinating to consider.

Reality isn’t much fun. Trout will make $33.25 million each of the next three years, and in the end, the current deal will have cost him somewhere around $50 million. Now, it’s awfully difficult to question the wisdom in a man turning down $144.5 million. There comes a point at which the money is so big it’s almost irresponsible to say no. It is impossible to say, too, whether Trout would have continued to play at an all-time historic level had he not signed the contract.

Presuming he did, he already has left somewhere in the neighborhood of $10 million on the table through arbitration alone. He would have shattered Ryan Howard’s first-year record and then gone on to reset the market in the years thereafter. Had Trout not signed his deal, the beneficiaries would’ve been players across baseball, who would’ve seen tens of millions more dollars in arbitration given the ripple effect of him constantly pushing boundaries.

Instead, it’s Harper who’s likeliest to see those double-digit years and that deal that begins with a four. It wouldn’t have been nearly as big a deal in the alternative universe where Trout is a free agent. The average of all 63 personnel people pegged his would-be deal at 11 years, $443 million – about as reasonable a half-billion-dollar investment as one will find, short of T-bills.

That’s Mike Trout: rock solid, easily relied upon, guaranteeing a return. The Angels are a very lucky team. And the rest of baseball only can sit there, wondering what it would’ve looked like this winter, what it will resemble come 2020 when this thought experiment finally becomes reality.

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