An arbitrator denied Rimas Sports' request for a temporary restraining order that would have allowed its main baseball agent, William Arroyo, to continue representing clients while navigating an appeal of his decertification, according to a court document obtained by ESPN.

The decision was made by arbitrator Michael Gottesman on Friday. On Monday, the Major League Baseball Players' Association made the procedural step of filing a motion with the Southern District of New York asking that the court uphold his decision.

Arroyo originally had his agent certification revoked on April 10 in the wake of an MLBPA investigation about improper benefits provided to players. Jonathan Miranda and Noah Assad, two prominent executives for the Bad Bunny-led agency, were also denied their applications for certification. Michael Velazquez, another certified agent who recently joined Rimas, must leave the agency by May 10 or face potential decertification, sources with knowledge of the situation said.

The MLBPA's penalty against Rimas consists of a $400,000 fine and, according to sources, a five-year suspension for Arroyo. Additionally, the notice of discipline prevents Miranda and Assad from applying for agent certification for five years, sources said. If upheld, the ruling would essentially end Rimas Sports' short-lived quest to represent baseball players in contract negotiations with major league teams. Rimas plans to file a full appeal of the decision through the American Arbitration Association by a May 10 deadline, sources familiar with the situation told ESPN. Spokespeople for the MLBPA and Rimas declined comment.

Within one week of Rimas' official launch in mid-April 2023, the MLBPA received evidence the company had offered players cash and gifts to switch agencies, according to sources. Section 5 of the MLBPA's agent regulations states that no agent "shall provide, cause to provide or promise to provide any money or any other thing of value to any player, or any person related to or associated with such player" for the purposes of persuading him to join or remain with an agency.

Bad Bunny, the world-famous Puerto Rican rapper and singer, launched the sports-management agency in April 2023 alongside his manager, Assad, who founded the independent record label Rimas Entertainment. Miranda was brought in as president. With the launch, Bad Bunny -- the stage name of Benito Antonio Martinez Ocasio -- hoped to follow in the footstep of hip-hop icon Jay-Z, who launched Roc Nation's sports-management division in 2013 and signed major clients across sports, such as the NBA's LaMelo Ball, the NFL's Saquon Barkley and MLB's CC Sabathia.

Rimas Sports focused on young Latin American baseball players, bringing in New York Mets catcher Francisco Alvarez, Mets infield prospect Ronny Mauricio, Colorado Rockies shortstop Ezequiel Tovar, Cincinnati Reds infielder Santiago Espinal and Los Angeles Dodgers catching prospect Diego Cartaya. Most of those players requested to be placed on the MLBPA's Do Not Contact list, preventing other agents from recruiting them while Rimas' standing is unsettled, a source said.

The company recently signed reigning National League MVP Ronald Acuna Jr. and is currently handling his marketing deals. The expectation, according to sources familiar with the situation, was that Rimas would eventually also represent Acuna in baseball matters. But the MLBPA's investigation and subsequent penalties has cast that into serious doubt.

ESPN's Jeff Passan and Jorge Castillo contributed to this report.