The San Diego Padres have gone all-in on their pursuit of the World Series in recent years, including when the team signed shortstop Xander Bogaerts on an 11-year, $280 million contract in 2022. After three seasons with the Padres, Bleacher Report’s Kerry Miller predicts that by 2027, Bogaerts' contract will be a nightmare for the organization.

“Bogaerts has already regressed drastically, giving the Padres a .705 OPS over the past two seasons compared to an .880 mark over his final five years in Boston [with the Red Sox],” Miller wrote in a recent article. “They still owe him more than $200 million over the course of the next eight years.”

The 13-year veteran’s decline is a bad sign for the Padres, as he’s already 33 years old but still under contract until the 2033 season. If he continues his pattern of regression, the final years of Bogaerts’ contract will be detrimental to San Diego.

In three seasons with the Friars, Bogaerts has recorded a slashline of .272/.331/.407 with 155 RBI’s and a 104 OPS+. It’s good numbers, but it's a far cry from what the shortstop put up in his final five years with the Red Sox.

Bogaerts put up three straight All-Star seasons at the tail end of his Boston tenure, winning a Silver Slugger award three times. His WAR in his final five seasons with the Red Sox, including a shortened 2020 season, was 23.3. In three seasons with the Padres, Bogaerts has accumulated just a 7.4 WAR. His regression isn’t just inevitable; it’s happening right now.

Third baseman Manny Machado will earn a ridiculous $39.1 million salary in 2027, but he’s still putting up great seasons for San Diego and looks like he can continue to make his contract worth it for the next couple of years. In contrast, Bogaerts is already falling behind Machado in terms of production.

Despite this, Bogaerts is still a good player for the Padres. He has a solid bat and still brings a lot of value at the shortstop position despite his age. He’s in the 94th percentile in terms of range, with his eight outs above average according to Baseball Savant.

Padres fans can only hope that his regression slows down, as he’s in the books for another eight years. It was a bold decision for the front office to sign Bogaerts for 11 years, and they may very well be having nightmares about it in just a couple of years.