Tuesday marks the 18th anniversary of the most transformative contract in American sports history. When Alex Rodriguez signed a 10-year, $252 million deal with the Texas Rangers, it rejiggered the notions of what an athlete could be paid. Curt Flood and Andy Messersmith forged the path for free agency, and Len Barker proved its value, and collusion in the 1980s illustrated how dangerous ownership believed it to be. Then came Barry Bonds and Albert Belle and the game’s first $100 million man, Kevin Brown. Until Rodriguez, the evolution was linear.

With one stroke of the pen, he more than doubled the previous record. It set off a panic. How could one player be guaranteed more than what half the franchises in the game were worth? If some baseball teams were losing so much money they might be contracted – they weren’t, but that was a popular talking point in 2001 – how much more inequitable would the game get? And most frequently: Just how high might salaries go?

It’s funny, that last one. Sport-wide revenues in 2001 were around $3.4 billion, which, adjusted for inflation, is $4.9 billion. Today, they’re around $10 billion – about double. Opening-day payrolls in 2001 averaged around $65 million – $93 million when inflation-adjusted. Last season, they were in the $130 million range, which isn’t even a 40 percent increase. And the biggest free agent contract in baseball history?

View photos Bryce Harper hits free agency with a career line of .279/.388/.512 with 184 home runs, 521 RBIs and an OPS+ of 139. (AP) More

The $275 million deal the New York Yankees gave A-Rod in 2007 when he opted out of his original 10-year deal. Less than a 10 percent bump.

All of this is important context for what’s primed to unfold in the next month. For the first time since Rodriguez’s initial foray into free agency, there is a player – actually, two – who come close to matching his combination of youth and excellence. Bryce Harper and Manny Machado are free agents now, and as the winter meetings begin Sunday at the Mandalay Bay in Las Vegas, their fortunes, both professional and monetary, are the most significant question in a sport riddled with them.

The parlor game of “Where will Bryce and Manny wind up and how much will they make?” is popular in conversations among executives, scouts and others inside the game, and the answers often morph into greater ruminations about the state of baseball writ large. Some are skeptical that Machado’s agent, Dan Lozano, and Harper’s, Scott Boras, will be able to extract even $300 million, which makes one wonder: How, exactly, can revenues double over the last 18 years and yet those who are among the game’s faces make around the same as their proxy a generation ago did? Others believe Harper and Machado will exceed $300 million but, along with Patrick Corbin’s $140 million deal with the Washington Nationals, will represent the only significant outlays this winter. Which makes players, already wary of ownership after last winter’s free agent freeze, think: Where, exactly, is all this money going if not to the players?

Harper and Machado are outliers. That’s a vital point to consider. Each is 26 years old when a vast majority of free agents are in their 30s. (A-Rod was 25.) Harper has been to six All-Star Games, Machado four. (A-Rod had attended four.) Harper hits free agency with a career line of .279/.388/.512 with 184 home runs, 521 RBIs and an OPS+ of 139. (A-Rod was .309/.374/.561 with 189 home runs, 595 RBIs and an OPS+ of 138.) Machado hits free agency with 33.8 wins above replacement, highlighting his value at third base and shortstop as well as with the bat. (A-Rod had 38.1 WAR.)

They may not be A-Rod, but Harper and Machado certainly reside in his gated community, and it’s reasonable to ask why, then, their paydays wouldn’t go up commensurate with the game’s revenues. The answer isn’t particularly satisfying: Because others’ haven’t since. And while that didn’t prevent former Texas Rangers owner Tom Hicks from investing a quarter-billion dollars in Rodriguez, the idea that owners to whom fiscal discipline is practiced as mandate would lavish a player simply doesn’t resonate. The outliers can be outliers. Just don’t pay them like it.