The San Diego Padres were willing to pay Aaron Judge well into his 40s to secure a deal for the American League MVP.
The New York Post's Jon Heyman reported the Padres "were contemplating a deal for $400 million-plus over 14 years."
On Wednesday, Bob Nightengale of USA Today reported San Diego made a 10-year, $400 million offer to Judge at the 11th hour. Adding four more years would've lessened the annual cost of the contract while taking him through his age-44 season.
Heyman noted MLB might have intervened had things gotten any further because it "would have seen the additional years as only an attempt to lower their official payroll to lessen the tax."
Judge agreed to a nine-year, $360 million deal to return to the New York Yankees.
The Padres haven't rested on their laurels after reaching the National League Championship Series in 2022. In addition to their failed pursuit of Judge, they made a run at Trea Turner before he signed with the Philadelphia Phillies.
After getting spurned by both players, San Diego turned around and landed Xander Bogaerts for a reported $280 million over 11 years.
Padres ownership has given president of baseball operations A.J. Preller the green light to spend over the last few years. That Preller was empowered to target Judge and Turner and ultimately sign Bogaerts is particularly fascinating, given the contract statuses of Manny Machado and Juan Soto.
Machado can opt out of the final five years and $150 million of his deal after the 2023 season. He'll be 31 next winter, three months younger than Bogaerts, so it stands to reason he can collect a better payout by hitting free agency.
Soto, meanwhile, is eligible to enter the open market in 2025 and could have one of the most frenzied bidding wars ever. ESPN's Jeff Passan posited Wednesday on The Pat McAfee Show that Soto and Los Angeles Angels star Shohei Ohtani could be the first players in MLB history to get $500 million.
If Machado and Soto don't sign long-term agreements before hitting free agency, then there are no guarantees about their futures in San Diego. The Padres at least appear to be showing they won't lose either player purely because they weren't willing to pony up the dough.