With their eyes shifting from rebuilding to contending, the White Sox have been on a spending spree lately, not only signing a fistful of free agents this winter but also locking up some of their most talented young players via long-term extensions. They struck again on the latter front on Thursday; via The Athletic’s Ken Rosenthal, they’ve agreed to a five-year extension with Yoán Moncada, their most valuable position player in 2019.

Moncada, who signed with the Red Sox out of Cuba for a record $31.5 million back in February 2015, topped the FanGraphs Top 100 Prospects list in 2017, shortly after being traded from Boston to Chicago in the Chris Sale blockbuster. He put together uneven performances at the big league level in 2017 and ’18 but began living up to that top prospect billing by breaking out in a big way in ’19, his age-24 season. While he missed three weeks in August due to a right hamstring strain, he hit a sizzling .315/.367/.548 with 25 homers and 10 steals. He tied for sixth in the AL in wRC+ (141) and placing ninth in WAR (5.7).

There was much to like about Moncada’s breakout on both sides of the ball. Despite a more aggressive approach at the plate that saw his O-Swing% jumped from 23.3% to 32.7%, and his overall swing rate from 41.1% to 47.3%, he cut his strikeout rate from 33.4% (yielding a league-high 217 strikeouts) to 27.5%. Not only did he make more frequent contact, he hit the ball much harder; his average exit velocity jumped from 90.6 mph to 92.8, seventh among all qualifiers, and his xwOBA shot from .302 to .362. On the defensive side, he seamlessly handled the move from second base, where he was subpar in 2018 (-3.7 UZR, -11 DRS), to third base, where he was more or less average (4.3 UZR, -4 DRS).

A performance like that is one worth investing in, and the White Sox are doing so via a five-year, $70 million deal that covers Moncada’s age-25 to age-29 seasons (2020-24); in other words, it runs from his final pre-arbitration season though his first year of free agent eligibility. The annual breakdown of salaries has not been announced as of this writing, but via ESPN’s Jeff Passan, he’ll be paid $65 million for the five years, with a $25 million club option and $5 million buyout for 2025, his age-30 season. Old Friend Kiley McDaniel reported that the deal also includes $2.5 million in escalators, pushing its maximum value to $92.5 million. That’s larger than all but one of the 18 previous extensions signed this offseason, namely that of Christian Yelich, whose pending $215 million extension was reported on Tuesday. On Monday, Jake Mailhot rounded up the other extensions while noting that there will likely be more as the spring progresses.

Moncada is the third young White Sox player to ink a long-term extension within the past year. The wave began in late March of 2019, with Eloy Jiménez inking a six-year, $43 million deal for 2019-24, a record for a player who had yet to play a single big league game; a pair of club options can run the total value of that deal to $75 million over eight years. In January, Luis Robert, who himself received a $26 million signing bonus in May 2017, broke Jiménez’s record by similarly agreeing to a six-year, $50 million deal for 2020-25, before his major league debut. He too has a pair of club options tacked on at the end, which can push the total value of the deal to $88 million over eight years. Earlier this month, the White Sox extended reliever Aaron Bummer via a five-year, $16 million contract that can max out at $29.5 million if its two club options are exercised. If this formula is starting to sound familiar, it’s worth noting that the Sox similarly signed Sale, Adam Eaton, and Jose Quintana to five-guaranteeed-plus-two-option extensions, and Tim Anderson to a six-plus-two extension. It’s clearly a formula that owner Jerry Reinsdorf and general manager Rick Hahn like; just spitballing here, but it wouldn’t be a surprise if starters Lucas Giolito and Reynaldo López — both of whom also have two-plus years of service time — sign similar contracts before Opening Day.

One can get a sense of why the Sox prefer to go this route by looking at Moncada’s ZiPS projection. Via Dan Szymborski:

ZiPS Projection – Yoan Moncada Year BA OBP SLG AB R H 2B 3B HR RBI BB SO SB OPS+ DR WAR 2020 .274 .341 .483 547 84 150 28 4 26 78 52 169 14 121 3 3.9 2021 .273 .341 .493 531 83 145 28 4 27 78 52 166 12 123 3 3.9 2022 .271 .341 .503 527 83 143 28 5 28 79 53 165 12 125 3 4.0 2023 .268 .338 .497 515 81 138 27 5 27 77 52 164 12 123 2 3.7 2024 .271 .342 .499 501 78 136 26 5 26 75 51 152 11 125 1 3.6 2025 .273 .341 .505 487 76 133 25 5 26 74 48 143 10 126 0 3.5

That projection weighs in at 19.1 WAR over his five guaranteed years and 22.6 WAR including the option. That comes out to less than $4 million per win either way, because those pre-arb and arbitration seasons arrive at a steep discount. Using $7.5 million per win for a free agent, with a 5% inflation rate — assumptions that, as Dan noted, still track as the best predictor of salaries including this winter’s deals — here’s how Moncada’s valuation stacks up if he were a free agent versus what he could have been expected to receive by going annually through the arbitration process:

Yoán Moncada Valuations Via ZiPS Year Service Time WAR $/WAR FA Value Adj Value 2020 Pre-Arb 3.9 $7.50 $28.9 $0.6 2021 Arb 1 3.9 $7.88 $30.5 $8.2 2022 Arb 2 4.0 $8.27 $33.1 $15.2 2023 Arb 3 3.7 $8.68 $32.0 $19.5 2024 FA 1 3.6 $9.12 $32.9 $32.9 2025 FA 2 3.5 $9.57 $33.8 $33.8 Total 2020-24 19.1 $157.4 $76.5 Total w/Opt 2020-25 22.6 $191.2 $110.3 SOURCE: Dan Szymborski’s ZiPSmobile Based on $7.5 million per WAR for 2020 and a 5% annual rate of inflation. For arbitration years 1, 2, and 3, salaries are reduced to 27%, 46%, and 61% of full value, respectively.

Via Dan’s methodology, on the free agent market Moncada’s projected production would be worth about $157 million over five years, or $191 million over six years, which sounds astronomical until you realize that, per the projection that Dan ran earlier this week, Francisco Lindor’s next five years, over which he’s estimated to produce 31.0 WAR, would be worth $256 million on the open market, with his six-year, 36.1 WAR projection valued at $303 million. Like every other young player who makes the mistake of being very good during his pre-free agency years, Moncada will only receive a fraction of his projected value, about 45% to 47% depending upon whether the option is exercised. Even with his pre-arb and arbitration salaries reduced significantly — the rates of which vary somewhat, as better players’ salaries are suppressed to a greater degree — that production projects to be worth $76.5 million over five years (about 9% more than he’s actually guaranteed) or $110 over six years (about 22% more). By signing the extension, Moncada has potentially left some money on the table, but protected himself against the risk that he might be worth much less. Virtually every player who goes this route makes a similar tradeoff.

Given that his deal will expire either after his age-29 or age-30 seasons, Moncada’s not in a terrible position to cash in once he does reach free agency. Anthony Rendon, who’s heading into his age-30 season, just signed a seven-year, $245 million deal. Conversely, Yelich, who signed a seven-year, $49.57 million contract in March 2015, just before he began his third major league season, faced a situation where he wouldn’t hit free agency until after his age-31 season, and thus had to settle for “just” an additional $188.5 million on top of the $26.5 million he was already locked into for his first two years of free agent eligibility.

With this extension, the White Sox now have every regular in their expected lineup save for rookie second baseman Nick Madrigal (who may or may not start the year in the majors) and right fielder Nomar Mazara (a December trade acquisition with four full years of service time) cost-controlled for multiple seasons; the tally also includes superutilityman Leury García, who signed a $3.5 million, one-year-plus-option contract in February. For as active as the team has been in locking up its youngsters, the Sox also spent significantly in free agency this winter, retaining first baseman José Abreu (three years, $50 million) and adding catcher Yasmani Grandal (four years and a franchise record $73 million) and designated hitter/first baseman Edwin Encarnación (one year plus option, $12 million) as well as lefty starters Dallas Keuchel (three year plus club/vesting option, $55.5 million) and Gio González (one year plus option, $5 million) and righty reliever Steve Cishek (one year plus — wait for it — option, $6 million).

With the arrivals, a team that hasn’t finished above .500 since 2012 (!) is forecast to win 84 games and has a 16.1% chance of winning the AL Central, with a 10.9% chance at a Wild Card spot. With so much young talent coming to fruition at the same time, the White Sox have created something of a dream scenario for a front office, as they can build around this core while remaining secure that its cost won’t grow too quickly for the team’s own comfort. And while Moncada may have left a bit of money on the table in agreeing to this extension, he’s already guaranteed that his career earnings will top $100 million, while still leaving himself a shot at attaining another huge payday while he’s relatively young.