The Milwaukee Brewers and outfield prospect Jackson Chourio are closing in on a record-breaking deal that will pay Chourio close to $80 million over the next eight years — despite the fact that the 19-year-old has played in only six games above the Double-A level. Still, the Brewers have enough faith in the ceiling and makeup of MLB Pipeline’s No. 2 overall prospect to give him the richest deal ever signed by a player without any big-league experience, surpassing the six-year, $50 million deal that the Chicago White Sox handed outfielder Luis Robert Jr. back in 2020.
But Chourio and Robert aren’t the only players to put pen to paper before they took their first cuts in an MLB game. Here’s a brief history of some other players to do the same, ranked in descending order of guaranteed money.
Largest contracts before MLB debut
1. Jackson Chourio, Brewers, November 2023
The contract: Eight years, $80 million
If you’d like to know just why Milwaukee why shell out this kind of cash for a 19-year-old, well, we go into greater detail here. The short version: Teenagers with top-of-the-scale speed, elite center-field defense and plus power don’t come around very often, and Chourio just hit 22 homers and 44 stolen bases across 128 games in Double-A and Triple-A last season.
2. Luis Robert Jr., White Sox, January 2020
The contract: Six years, $50 million
Speaking of freak athletes in center field! Much like Chourio, Robert Jr. shot up prospect lists thanks to his combination of power, speed and defense. Milwaukee can only hope that this deal works out as well: Robert Jr. has compiled a 124 OPS+ and 12.5 bWAR since putting pen to paper, and he’s the one player Chicago has to build around as new GM Chris Getz embarks on a rebuild on the South Side.
3. Eloy Jiménez, White Sox, March 2019
The contract: Six years, $43 million
Jiménez, on the other hand, hasn’t worked out so well. He looked like a budding star as a rookie, finish fourth in AL ROY voting and homering 31 times in 122 games. Injuries have dogged him ever since, though: He appeared in just 139 games across 2021 and 2022 and struggled to a .272/.317/.441 slash line this past season, hardly good enough for a player whose body limits him to DH duties. 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.
T4. Scott Kingery, Phillies, March 2018
The contract: Six years, $24 million
A consensus top-50 prospect at the time he signed this deal, Kingery was supposed to help usher in a new era of Phillies baseball. Alas, it never materialized: He struggled mightily at the plate as a rookie, and while he bounced back a bit in 2019, the bottom has since fallen out. Kingery has played in just 52 big-league games since the start of 2020, his most recent cup of coffee coming in a single appearance back in 2022. The guaranteed portion of his contract elapsed at season’s end, resulting in him becoming a free agent.
T4. Evan White, Mariners, November 2019
The contract: Six years, $24 million
Similarly, White was among Seattle’s top prospects in the fall of 2019, an excellent defender at first base who projected as a plus hitter in the Majors. He lived up to the billing with the leather, winning a Gold Glove Award in 2020. It was a different story at the plate, however: White posted a dismal .165/.235/.308 line over the 2020-21 seasons, and injuries have limited him to just 116 at-bats in the Minors since.
6. Jon Singleton, Astros, June 2014
The contract: Five years, $10 million
Singleton’s deal was the first of its kind at the time, as the Astros — then still in the midst of their rebuild — locked up a significant piece of their future just before he made his MLB debut. The first baseman was mashing in Triple-A at the time, but his bat never quite made the jump to the Majors, as he hit .171/.291/.331 in 420 plate appearances over the ensuing two seasons before running afoul of MLB’s (rather antiquated) policies against marijuana usage.
Singleton was largely relegated to Triple-A for the duration of that initial contract, and he later had to play in Mexico before returning to pro ball in the States. He did fight his way back to the Majors in 2023, first with the Brewers and then in a reunion with Houston, even making a couple of appearances in the Astors’ ALCS loss to the Rangers. He’s still yet to make good on his potential, however, and it remains to be seen whether he has a future in Houston moving forward.