Tim Anderson, last of the White Sox’s big-time bargains

As long as Michael Conforto remains on the market as a proven solution to the White Sox woes in right field, we've still yet to learn if Rick Hahn is sticking to his definition of "spending the money."

Here's where he left it last winter after the White Sox added Liam Hendriks and not much else:

This winter/spring has done nothing to change the conversation, because he chose to add three relievers (Kendall Graveman, Joe Kelly, picking up Craig Kimbrel's option). Leury García and Josh Harrison fail to move the needle on the position-player side.

In classic lawyer sense, Hahn wasn't wrong. This year's payroll is going to set a record by plenty. The problem is that the "long-term commitments" referenced by Hahn used to mean one thing, and now they mean another.

It's not all bad -- the White Sox figured out how to acquire more than four core players, which differentiates it from the first rebuild. They have an above-average number of players under contract, they're all set to get paid increasing amounts, and they all deserve said amounts and then some. That much is fine.

But the cost of extensions also rose, because you can only sign so many deals considered no-brainers by the general public before it becomes a criticism of the players' negotiation skills. Each subsequent player committed to an extension earlier in their careers, and for more money. They remained good deals, but they lacked the room for surplus value that guaranteed spending power elsewhere.

In the end, Hahn effectively promised White Sox fans a trip to Disneyland ... Orthodontics. The phrasing and cadence worked for placating the rabble after coming up well short in major free-agent pursuits, as long as he understood that easier flossing wasn't the reward they had in mind.

Tim Anderson is the last vestige of the possibilities extensions used to open. He would've been on the cusp of free agency right now had he not signed a six-year, $25 million extension before the 2017 season. The deal included a pair of options to cover his first two years of free agency, starting with a $12.5 million decision after the 2022 season that's a virtual lock regardless of what happens between now and November.

The ink dried just five years ago, but the context shifted considerably since then. While it looks like robbery on the White Sox's part now, his contract seemed to incur some real-time risk. His deal represented the biggest extension ever awarded to a player with less than one full year of service time, beating Chris Archer's six years and $20 million from the Tampa Bay Rays. Anderson's severe strikeout-to-walk gap during an otherwise impressive rookie year made regression a real threat, and sure enough, he failed to clear a .700 OPS in either of the next two seasons.

With playable defense and above-average speed, Anderson had enough to the rest of his game to make a lesser-percentile outcome tolerable. Unless everything cratered, he'd be an average up-the-middle player paid accordingly. But Anderson's success over the last three seasons -- .322/.349/.495, a batting title, a top-10 MVP finish, a Silver Slugger, an All-Star appearance -- shows why those sorts of deals became reflexively desirable for teams, and why the cost of securing the first year or two of free agency has only risen since.

Here's how much the next three position-player extensions cost the Sox:

And if it it feels like I've already written this post, you're not entirely wrong. I'm good for one of these every two years ...

• February 2018: This White Sox rebuild can't hinge on extensions
• January 2020: Extensions take different shape in this White Sox rebuild

... which means this installment is right on time.

Beyond pure bienniality and the recurring themes of our ongoing 16-year conversation, there are a couple of reasons to revisit the topic. The White Sox are revisiting Anderson's past with a five-part documentary, with the first installment going live this morning.

Meanwhile, an unprecedented class of shortstop talent just finished finding new homes around baseball, all of whom are earning well more than Anderson over the next two years, which would've been his first two years of free agency.

This is the level of savings that these early-career contract extensions used to ensure. When the Cubs acquired José Quintana from the White Sox, Theo Epstein talked about how Quintana's salary allowed them to consider him a player and a half, because the salary he deserved but didn't capture could be redirected to another player. It ended up being Yu Darvish, and while the Cubs couldn't get enough individual elements aligned for a major payoff, Epstein's description remained apt.

Anderson has that same player-and-a-half thing going for the next couple years, and he's one of the few players who represents savings that can be redirected in a meaningful way. Except the way Hahn describes it, that money was merely directed toward players who were already on the payroll, rather than solving the last remaining gaps in exciting ways. The extension Robert signed was described as "superstar insurance,", and the Sox have to go about the boring business of paying the premium.

That wouldn't be an issue, except the White Sox roster is still in a weird spot where all of the impact players required considerable acquisition cost, whether in terms of dollars, players, or draft position.

International circumstances no longer allowed/impossible to duplicate: Luis Robert, José Abreu

Trading valuable, established big-leaguers: Yoán Moncada, Lucas Giolito, Eloy Jiménez, Dylan Cease, Michael Kopech, Lance Lynn, Reynaldo López

Market-rate free agency: Yasmani Grandal, Dallas Keuchel, Liam Hendriks, Kendall Graveman, Joe Kelly

Excessive amounts of losing: Andrew Vaughn, Craig Kimbrel.

Granted, it may not look this tilted next year. You have Garrett Crochet and Jake Burger from the middle third of the first round, and Aaron Bummer and Adam Engel were nice finds in the 19th-round. Bummer is the only one who's established himself as more than fungible, but Engel's shown promise, and Gavin Sheets leads a group of emerging prospects from humble origins.

Still, after Robert joined Jiménez in signing record extensions before their first MLB games, I'd noticed that the Sox had no peers at their level of commitment to pre-MLB players. Two years later, they still don't.

Why haven't any of the other 29 teams followed Hahn's lead? Perhaps it's because Hahn truly has an uncommon touch with long-term extensions, or Abreu's presence inspires teammates more than can be quantified.

However, if the cost of long-term extensions mean that they no longer generate new opportunities by savings alone, then perhaps teams don't see enough value in the cost certainty to lock in those salaries that far in advance. In this scenario, teams are either content to trade those players before their sixth or seventh year arrives, or they'll strike a nine-figure extension to eliminate the free-agent conversation for longer.

There's also the chance that this snapshot is merely an unflattering frozen frame in a rosier big picture. Maybe Vaughn is indeed a decent corner outfield option after his offense matures. Maybe Sheets and Burger take next steps, or Yoelqui Céspedes and Oscar Colás spring surprises on the prospect listmakers, giving the Sox those needed contributors from less losing-specific origins. Add in another winning season with the inefficient contracts of Keuchel and Kimbrel coming off the books, and this year represents a spending lull between significant pushes. The White Sox had never made the postseason in consecutive seasons before now, and they're setting out to string together division titles for the first time in franchise history, so it's hard to say. They have it within them to be a force, especially with a deep postseason run,

All we can say for the time being is that the White Sox's creative accounting is getting less rewarding for fans, save a CPA or two who might be jazzed about Hendriks' 10-year buyout, and they might've stiff-armed the truly expensive decisions for as long as they could. Anderson's the last of the guys who truly did the White Sox's year-to-year ledgers a favor, and he'll be ready for his reward if it's still there.