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In November, the Milwaukee Brewers and outfield prospect Jackson Chourio agreed to a record-breaking deal that will pay Chourio $82 million, The agreement established a new precedent for contract extensions signed by a player prior to their MLB debut. 

Chourio, recently ranked by CBS Sports as the No. 7 prospect in the minors, has played in only six games above the Double-A level. Nevertheless, the Brewers have enough faith in his potential and his makeup to give him the richest deal ever signed by a minor-league player who lacked any big-league experience. The previous record had belonged to Chicago White Sox outfielder Luis Robert, who signed a six-year agreement worth $50 million back in January 2020. 

Chourio and Robert aren't the only players to put pen to paper before they took their first cuts in an MLB game. In fact, Chourio isn't even the only one this offseason: Tigers infielder Colt Keith has agreed to a six-year, $28.6425 million extension to stay in Detroit through his arbitration years.

Below, CBS Sports has offered a brief history of the other players to do the same. Do note that the players are presented from largest contract to smallest in terms of guaranteed money.

1. Jackson Chourio, Brewers OF, November 2023

  • The contract: Eight years, $82 million

Chourio won't turn 20 until March 2024, the same month he could potentially make his MLB debut. CBS Sports ranked Chourio as a top-10 prospect in baseball because of power and speed. Chourio had a breakout season across the low minors in 2022 and followed it up with 22 homers and 44 stolen bases in 128 minor-league games in 2023.

2. Luis Robert, White Sox OF, January 2020

  • The contract: Six years, $50 million

Without question, Robert's has been the best of these deals for the team. Robert has compiled a 124 OPS+ and 12.5 Wins Above Replacement since 2020 thanks to an outstanding combination of power, speed, and defense. He's one of the most exciting players in the majors, and reportedly the only player on the White Sox roster that they're unwilling to seriously discuss in trades. When the Brewers think about what the future may hold for Chourio, this is what they're hoping for.

3. Eloy Jiménez, White Sox OF, March 2019

  • The contract: Six years, $43 million

Jiménez, who signed his deal about a week before Opening Day, ended up finishing fourth in Rookie of the Year Award voting after homering 31 times in 122 games. Injuries have since prevented him from matching or exceeding either total, though he did win a Silver Slugger Award in 2020 after launching 14 home runs in 55 games. For his career, he's amassed a 118 OPS+. The White Sox have discussed Jiménez in trades dating back to the deadline, suggesting that his time with Chicago might be nearing its end before he reaches a pair of club options (for the 2025-26 seasons) worth an additional $35 million. 

4. Colt Keith, Tigers IF, January 2023

  • The contract: Six years, $28.6425 million

The Tigers got themselves a steal in the fifth round of the 2020 draft in Keith. He has done nothing but hit as a pro -- Keith is a career 300/.382/.512 hitter in the minors -- and he cemented himself as a fixture in Detroit at either second or third base. The Tigers are on the rise and the AL Central is a winnable division, and this move adds another impressive young bat to their lineup. Keith will join Riley Greene and Spencer Torkelson as the young position players the club builds around moving forward. His contract includes three club options and can max out at nine years and $82 million.

T5. Scott KingeryPhillies 2B, March 2018

  • The contract: Six years, $24 million

Kingery, a speedy infielder, was supposed to help usher in a new era of Phillies baseball. He struggled mightily in his rookie season, hitting for a 61 OPS+ in his first 147 games. He did manage a better sophomore effort, even clearing the league-average line, yet he lost his momentum from there. Kingery has since played in all of 52 big-league games, including a single appearance in 2022 that serves as his most recent cup of coffee. The guaranteed portion of his contract elapsed at season's end, resulting in him becoming a free agent.

T5. Evan WhiteMariners 1B, November 2019

  • The contract: Six years, $24 million

White was known foremost as an excellent first-base defender with a contact-over-power bat when he inked this deal with the Mariners. He lived up to his billing with the leather, winning a Gold Glove Award in 2020. Unfortunately for White, he hit for a 52 OPS+ in 306 plate appearances over the 2020-21 seasons. He's since been sidelined by injuries, including of the hip and groin variety, that limited him to two Triple-A games for the duration of 2023.

7. Jon Singleton, Astros 1B, June 2014

  • The contract: Five years, $10 million

Singleton was mashing in Triple-A when the Astros signed him to the first deal of this kind and promoted him to the majors. His bat didn't transfer against superior pitching. He hit .171/.291/.331 (76 OPS+) in 420 plate appearances over the ensuing two seasons before running afoul of MLB's old policies against marijuana usage. He was largely relegated to Triple-A for the duration of the contract, and he later had to play in Mexico before making his way back into organized ball. It is worth noting that Singleton resurfaced with the Astros last season as part of those comeback efforts, even making a couple of appearances in the ALCS after rejoining Houston midseason. Alas, he continued to disappoint with his lack of production, preventing the fairytale ending.