Tricky Contracts Could Hamper The Padres Moving Forward

San Diego Padres' president of baseball operations A.J. Preller often receives major kudos from his peers and the MLB media for being a go-for-it kind of guy. Just look at how often he turns the trade deadline into a one-man three-ring circus featuring significant trades that seem to come at the rate of about one every 10 minutes.

Just since 2020, when San Diego's current window of contention began to fully open, these are among the marquee names he has acquired for the stretch run: 2020 - pitchers Mike Clevinger and Trevor Rosenthal; 2022 - outfielder Juan Soto, first baseman Josh Bell and closer Josh Hader; 2024 - closer Tanner Scott and relief pitcher Jason Adam; 2025 - closer Mason Miller; and 2026 - starters Casey Mize and Robbie Ray.

While all of these deals have not yet allowed Preller and the Padres to achieve the ultimate goal - winning the franchise's first World Series title - they have made the team a regular participant in the playoffs, with 2026 the third straight season in which they have moved to the postseason, a franchise first.

The moves have also essentially gutted the team's farm system, with MLB Pipeline currently ranking San Diego's prospects last among MLB's 30 teams.

It is one long-view transaction, however, that Preller made back in December 2022 that may turn out to be shortsighted. That's when he signed Boston Red Sox shortstop Xander Bogaerts to an 11-year, $278-million free-agent deal that will pay him nearly $25.5 million a season from now until the conclusion of the 2033 season, when Bogaerts will be 40.

Though Bogaerts finished with a strong month of September and showed a spark in the Padres' six-game postseason run against the Chicago Cubs and Milwaukee Brewers, hitting .286 (6-for-21) with a double, home run, two RBIs and four runs scored, with some sparkling defense thrown in, that came on the heels of a less-than-memorable regular season.

Bogaerts did appear in 153 games, his most since 2023, but he could muster only a .231 batting average, a career-low, and .676 OPS, his lowest since 2014 when he was a 21-year-old rookie with the Red Sox.

Bogaerts' seemingly diminishing production comes at a bad time for the Padres as MLB enters into an uncertain future. All indications are that the owners will lock out the players on Dec. 1 - hoping to introduce a hard salary cap to the game - setting the stage for a prolonged and painful work stoppage that could linger well into the 2027 season.

Though all signs have been positive through the first two months of the relationship, there are also still significant unknowns attached to the question of how new owners Jose E. Feliciano and Kwanza Jones, who officially acquired the Padres on Aug. 17, will operate the team, especially in regard to how loose their purse strings will be.

That means Preller's only recourse may be to try to trade Bogaerts, but that will be easier said than done, first because of the aforementioned seven years remaining on his contract and second, because the contract contains a no-trade clause and no opt-out language.

That could leave the Padres hamstrung, according to Tremayne Person of Friars On Base. Discussing a possible Bogaerts trade, he wrote on Oct. 11, that, "The Padres cannot ship the contract to whichever team offers the most convenient financial relief. He would have to approve the destination. A workable trade would probably require the Padres to cover a substantial piece of the remaining salary, accept another undesirable contract or include young talent to make the deal palatable. They could end up using all three levers."

Another possibility is that other teams, knowing Bogaerts is unmovable and smelling blood in the water, could start asking for other players in any trade like outfielders Fernando Tatis Jr. and Jackson Merrill or closer Mason Miller.

Tatis is under contract for eight more seasons with a $25.7 million salary in 2027 and 2028 that escalates to $36.7 million from 2029-34. Merrill's 10-year extension that he signed before this season pays him $7.1 million, $9.1 million and $11.1 million from 2027-29 and $21.1 million a year from 2030-35. Miller, the MLB co-leader in saves this year, earned $4 million in 2026 and becomes arbitration-eligible after the 2027 season with free agnency looming after 2030. 

The Padres would likely attempt to lock Miller up to a long-term deal before then, but the labor and new-ownership uncertainty, along with the presence of some hefty contracts like Bogaerts', may ultimately make that difficult to do.