At the news conference officially welcoming Xander Bogaerts to the San Diego Padres, he tried on a pin-striped Padres jersey emblazoned with "2" on the back as A.J. Preller, the team's president of baseball operations and general manager, looked on with a smile as big as the USS Midway docked in San Diego Harbor.

And why not? Bogaerts' path to the Padres certainly seemed unlikely at the outset of the offseason, but after the Padres first aggressively pursued and failed to sign either Aaron Judge or Trea Turner, Preller turned his focus to Bogaerts and landed the four-time All-Star shortstop with an 11-year, $280 million contract. Bogaerts joins a star-studded Padres lineup that already features Manny Machado and Juan Soto, with Fernando Tatis Jr. returning after he missed all of 2022.

It was a stunning signing for a player who had been predicted to receive a contract more in the range of $160 million to $190 million.

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"It's crazy how the world works," Bogaerts said.

That's one way to explain what has happened so far this offseason. Until this month, nine players in major league history had signed contracts with a total dollar amount of more than $275 million -- and all nine of those players started the first year of those contracts while still in their 20s. Now we've had three players ink contracts for at least $280 million while beginning those deals in their 30s:

  • Bogaerts will be entering his age-30 season in 2023.
  • Turner signed an 11-year, $300 million deal with the Philadelphia Phillies while also entering his age-30 season in 2023.
  • Then the big one: Judge signed a nine-year, $360 million deal with the New York Yankees as he begins his age-31 season.

On top of that, Jacob deGrom, coming off two injury-plagued seasons, signed a $185 million deal -- the seventh largest for a pitcher -- with the Texas Rangers as he enters his age-35 season. And Justin Verlander, who will turn 40 in February, signed a two-year deal with the New York Mets that ties him with teammate Max Scherzer for the highest annual average value in the sport at a non-Scrooge $43.333 million.

The executives negotiating these contracts -- with the support of their owners -- certainly understand the risks of long-term deals for players in their 30s. Preller or Dave Dombrowski, who signed Turner, don't realistically expect Bogaerts and Turner to be starting shortstops when they're 41. They're exponentially more focused on winning in 2023 than on how these deals affect the payroll in 2033.