Ortiz: Red Sox owner John Henry ‘worried’ about team’s decline

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Ownership Anxiety in Boston

The Boston Red Sox, a franchise once defined by dominance, are currently navigating a period of significant instability. At a recent celebrity golf tournament, known as the David Ortiz Soiree of Hearts, the legendary former Designated Hitter and First Baseman suggested that the team’s leadership is feeling the pressure. According to reporting from The Washington Post, owner John Henry is “worried” about the current direction of the club, which has struggled significantly in recent seasons. Ortiz, who played 20 seasons and helped deliver three World Series championships to Boston, noted that he has spoken with Henry recently regarding the team’s difficulties. The sentiment from a figure like Ortiz carries immense weight in New England. As noted by Baseball Reference, Ortiz’s career was marked by elite production, including 541 home runs and a .286 lifetime average. His transition from a cornerstone player to a vocal observer of the team’s decline highlights the disconnect between the championship era and the current last-place standing.

A Historic Weekend at Churchill Downs

While the Red Sox face an uncertain future, the Ortiz name was recently celebrated in the world of Thoroughbred racing. On May 2, 2026, Jose Ortiz secured his first Kentucky Derby victory, completing a rare and historic double by also winning the Kentucky Oaks the previous night. Aboard the 23-1 longshot Golden Tempo, Jose Ortiz managed to edge out the 5-1 favorite, Renegade, by a mere nose at the finish line. The victory was particularly poignant as it came in a head-to-head battle against his older brother, Irad Ortiz. As USA Today reported, the brothers grew up in the same house in Trujillo Alto, Puerto Rico, and have maintained a lifelong sibling rivalry that culminated on the biggest stage in American racing. The financial windfall for Jose Ortiz following this weekend was substantial. The Kentucky Derby carries a $5 million purse, with $3.1 million designated for the winner. Based on a standard 10 percent jockey share, Jose earned $310,000 from the Derby alone. When combined with the $90,000 earned from his Kentucky Oaks victory, the weekend represented a massive surge in gross pay.

Jockey	Career Starts	Career Wins	Career Earnings
Jose Ortiz	18,900	3,581	$311,776,409
Irad Ortiz Jr.	22,195	4,546	$392,928,485

Scrutiny and Allegations in Puerto Rico

The celebration of the Ortiz brothers’ racing dominance has been abruptly overshadowed by a growing controversy. A USA TODAY Sports investigation published on May 14, 2026, has linked both Jose and Irad to alleged involvement in illegal activity in Puerto Rico, specifically related to cockfighting. The investigation traces a series of digital footprints that suggest the brothers have been connected to the controversial sport for some time. These include:

• A video from November 2025 appearing to show the brothers in a cockfighting arena, allegedly collecting money from bettors.
• A Facebook post from December 17, 2025, listing the brothers under a section for participants in a tournament titled “Caribbean Grand Champion.”
• An image from January 15, 2024, showing the pair standing with a known cockfighting breeder and promoter at Club Gallistico de Naguabo.

The fallout from these revelations has been swift, drawing condemnation from animal rights advocates. Kathy Guillermo, senior vice president of PETA, has called for officials to investigate the matter and potentially bar the brothers from future Eclipse Award nominations.

“With the horse racing industry already plagued by doping, horse deaths and horse abuse scandals, the last thing it should celebrate is jockeys who engage in egregious cruelty to other animals in a jurisdiction where it’s illegal.”

Kathy Guillermo, PETA

The Looming Preakness Stakes

The timing of these allegations could not be more precarious for the Ortiz brothers. As the racing world prepares for the Preakness Stakes, the brothers are facing questions about their eligibility and professional standing. Jose Ortiz is scheduled to ride Chip Honcho in the Preakness, fueled by the momentum of his Derby win and a desire to pursue the Triple Crown on different horses. Despite the investigation, he remains focused on the competition, stating, “Trying to win the Triple Crown on different horses, why not?” However, the shadow of the investigation remains. While the Kentucky Horse Racing & Gaming Corporation (KHRG) has investigated the brothers in the past, the current allegations regarding illegal activity in Puerto Rico present a different set of legal and ethical challenges. Whether the brothers will be allowed to compete, or if the scrutiny will result in formal sanctions, remains the most pressing question in the sport heading into the next leg of the Triple Crown.