Extensions take different shape in this White Sox rebuild

Back in February of 2018, I wrote that the second White Sox rebuild couldn't hinge on extensions the way the first relied on Chris Sale, Jose Quintana and Adam Eaton affording the Sox a bunch of budgetary leeway, even if they ended up squandering it. Rick Hahn was coming off a contentious offseason with regards to his own players, as Yolmer Sánchez and Avísail García both went to arbitration and won. He had company in the executive suites, as an unusually large number of players went to court, which might have been a response to the free-agent freeze. In that climate, it seemed less likely that players would so willingly sign deals that made them extreme bargains in the eyes of the baseball-watching public, especially if it pushed their first bite at free agency near or beyond age 30.

Well, in the following two offseasons, Hahn has struck deals with Eloy Jiménez and Luis Robert, buying out two years of free agency apiece and delivering striking blows to my powers of foresight.

Kinda.

The White Sox indeed locked in Jiménez and Robert for values that will underpay them should they reach even 80 percent of their potential. However, Hahn had to work a lot harder to convince these young stars to sign.

Look at how White Sox extensions have escalated since Sale signed his extension in March of 2013:

Granted, inflation has something to do with that, but its effect should theoretically be diminished by the gap in experience. Sale, Quintana and Eaton all had above-average seasons in the majors before they signed their deals, while the Jiménez and Robert signed before their first MLB game. Even then, their extensions easily outpace those of their predecessors, and Robert managed to top Jiménez by plenty despite a professional track record that's both shorter and more plagued by injuries.

That the White Sox went above Jiménez's contract for Robert provides further evidence as to how much Major League Baseball's salary structure underpays players for their earliest productive seasons, but Robert did a decent job at shrinking the room between what he will make and what he could make.

The options in the Quintana and Eaton contracts were automatic yeses so long as each player was healthy and decent. Robert's extension requires him to be good in order to really feel the value. It protects the Sox against a Mookie Betts/Kris Bryant/Francisco Lindor trajectory, but if Robert turns into a good-but-flawed regular (Jackie Bradley Jr.?) or an injury-prone star (Grady Sizemore?), his latter-year salaries will be more in line with what he'd get on the open market.

That's progress for the player and that's great. It just changes the purpose of these extensions. They're no longer as generous to the mission of team-building, but they're quite useful to the mission of team-sustaining assuming the rebuild works. They're less designed for getting the party started and more geared toward keeping the party going.

From here, I wonder how much the rest of baseball will follow suit. There are now only five such cases where a team signed a player to an extension before his first MLB game, and the White Sox have two of them. It's a copycat league, but the White Sox aren't often in the position of a team worth emulating, and I'm curious whether these deals are seen as genuinely admirable maneuvers. Or, like their historically conservative approach to free agency, these extensions represent another byproduct of a front office that counts on being in the same chair six to eight years from now no matter the result, and wants to protect itself from any huge messes.