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Padres Players Hold No. 1 and No. 2 Spot For Nightmare Contracts By 2028 cover image

Padres stars Machado and Bogaerts project as MLB's worst contracts by 2028, fueling financial woes for years to come.

The San Diego Padres have been in win-now mode for a few years, and it's resulted in back-to-back 90+-win seasons. Though there’s been a lot of exciting and winning baseball being played at Petco Park, there is a cost to keeping together such a talented team.

San Diego is already in a financial pinch this offseason, limiting their ability to make moves in free agency and retain players like starter Dylan Cease, who left for the Toronto Blue Jays on a $210 million deal. With the financial issues already coming about for the Padres, it’s only going to get worse as the years go on.

The Friars are already on the books for over $122 million in 2033 for just four players: outfielder Fernando Tatis Jr., outfielder Jackson Merrill, third baseman Manny Machado, and shortstop Xander Bogaerts.

Considering the age of both Machado and Bogaerts, it comes as no surprise that Bleacher Report’s Kerry Miller projected both of their contracts to be the worst and second-worst in the MLB by 2028.

Machado, 33, has still been able to provide tremendous value for the Padres, bringing in 27.1 WAR over his seven seasons with the team. Though it’s obvious he isn’t at the same level he once was in the early 2020s, he provides enough value to make up for his $25 million next season.

After that, however, his salary skyrockets to $39.10 million until it expires in 2033. The end of that contract is certain to be ugly, as he’ll be 41 years old. His placement at second on the list of nightmare contracts by 2028 isn’t exactly a surprise, but it’ll only get scarier as each year beyond 2028 passes.

Bogaerts takes the crown for projecting to be the worst contract in three seasons, as he’ll be making $25.45 million at 36 years old. In baseball terms, 36 is an age where many can still be very productive. It’s different for Bogaerts, however, as he’s already shown alarming signs of regression since he signed with San Diego in 2023.

He’s seen just one season in San Diego with a WAR of over 2.0, which was his first year with the club. Since then, Bogaerts has become a below-league-average hitter after being a five-time Silver Slugger with the Boston Red Sox. If he continues his rapid downward trend at the plate, Bogaerts’ contract will certainly haunt Padres fans in their sleep. It’s already projected to be bad in 2028, but it’s only going ot get worse from there until his deal finally expires in 2033.

That’s the sacrifice teams make sometimes to put a winning team on the field. Hopefully, San Diego can find a way around the Machado and Boagerts contracts holding its franchise back for years to come.

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