Baseball has long been known as America’s pastime, a sport shaped by history and loyalty. It is woven with tradition and remembered through numbers that define generations. But behind the bright lights and packed stadiums lies another story. One whispered in locker rooms and front offices. These secret deals changed the course of teams and players.
Fans recently gathered on Reddit to ask a simple but loaded question: what was the biggest under the table contract in MLB history? The answers revealed stories of rule-bending and hidden promises. They also highlighted the constant battle between owners, players, and league officials over money and power.
The Braves Scandal and its Fallout
The most infamous case came in 2017 in the form of the Atlanta Braves. They were caught breaking international signing rules. According to u/dgmilo8085, MLB voided several deals and stripped the Braves of top prospects. They also banned their general manager John Coppolella for life. Although his ban was later lifted, the punishment was severe. It sent shockwaves through the league. The main player at the center was Kevin Maitan, a teenage shortstop from Venezuela. He had been hyped as the “Venezuelan Miggy” for his swing that drew comparisons to Miguel Cabrera.
When the league voided the contracts, Maitan and several other prospects were declared free agents. Most of the young players had their careers thrown into chaos. Some landed outside of the Majors and never found their way back to the top leagues. For the Braves, the scandal was a turning point. They paid the price in public embarrassment and on the field, with their farm system gutted overnight.
As one commenter noted, the Braves’ later team-friendly contracts with stars like Ronald Acuña Jr. and Ozzie Albies only fueled speculation. Fans wondered about what might have been happening behind closed doors.
Albert Pujols and the Strange Personal Services Deal
Moving on, one of the most talked about was Albert Pujols’ “personal services” contract with the Los Angeles Angels. The agreement guaranteed Pujols a job with the Angels once his playing days were over. It mixed the idea of paying for what he did on the field with paying for what he might represent later. As one fan pointed out, it was perfectly legal but felt like an extra side deal tacked onto his playing contract.
To critics, it looked like a clever way to add value without putting the full amount into his active contract. To supporters, it was a fitting way to honor one of the greatest hitters of his generation.
“LA paid over 20 million for every 1 WAR Albert produced.” — u/IhaveAthingForYou2, 2025
For many fans, the Pujols deal became a symbol of the uneasy marriage between legacy and money in baseball. It was never about what he produced between the lines.
Hidden History and Tales from the Past
With modern examples getting all the headlines, some fans pointed out that under the table deals go back to baseball’s earliest days. u/MorningRooster shared that Lip Pike and other Philadelphia A’s players were quietly paid in the 1860s. This scandal helped end amateurism and open the door for professional baseball.
Another fan pointed to Bob Feller, who signed his first deal for just $1 when he was only 16 years old. At the time, MLB rules banned clubs from signing high school players. But Cleveland worked around it. They did this by striking an unofficial deal with Feller and his father, essentially locking him in before he was even eligible.
Fast forward to recent past, Shohei Ohtani’s unprecedented contract with the Dodgers raised eyebrows across the league. Officially, it was a 10-year, $700 million deal. However, Ohtani deferred more than $680 million of that money to the future. The deferrals lowered the Dodgers’ immediate payroll hit. This gave them more room to sign other players. Fans on Reddit wondered aloud if this arrangement was just creative accounting or something closer to an under the table benefit.
