The San Diego Padres once again find themselves at the start of a pivotal offseason, but what makes this coming winter so unique is that it is the first for new owners Kwanza Jones and Jose E. Feliciano after spending $3.9 billion to purchase the team earlier this year.

President of baseball operations AJ Preller, who was been at the helm since 2021 after taking over as general manager in 2014 (the second-longest tenured GM in baseball), enters the sixth full offseason he is overseeing things. Four of the last six years under his leadership have ended in the postseason, but only one of those years ended as far as the National League Championship Series.

Preller has no evidence to suggest that it is a championship-or-bust season, but if there ever was such thing as a championship window, there is a fleeting feeling surrounding it ahead of 2027.

The new ownership duo expressed their desire to win earlier this month, and word has clearly gotten down to the players as well. Right-hander Joe Musgrove spoke after being eliminated in the National League Division Series on buying into Feliciano and Jones' leadership and trusting their process ahead of their first offseason as owners.

“They’ve got our full support, and we know that they’re all about winning this thing,” Musgrove said. “So, we expect some moves in the offseason. You know: Revamp the group, get the pieces that we need and come back and make another run at it.”

Musgrove's points are exactly why this offseason should be the biggest yet for the front office.

Preller has a reputation of being one of the most active and aggressive executives in baseball. He creatively handles various financial situations regarding new talent being brought in, and does so with a few contracts that are not the easiest to navigate, to say the least.

Manny Machado will be 34 years old next season, and though he showed no signs of slowing down in terms of home runs (30), he had his lowest bWAR (1.5) and OPS (.711) of his career. He is owed more than $39 million every year through 2033.

Xander Bogaerts, who will also be 34 next seasaon, had a .676 OPS last season and is owed over $25 million per year through 2033. Both of these veterans have a no-trade clause included in their deals if it came down to it.

With most of the starting rotation entering free agency, an enormous opportunity presents itself for the front office. The combination of injuries to the pitching roster as well as poor performances totaled a dominant bullpen being overworked for 647.2 regular season innings, the second-highest in baseball.

The overuse was apparent in the postseason, but the regular season dominance of the bullpen is something that should be highly-valued over the offseason. A key name of the bullpen that has tons of uncertainty surrounding him this offseason is Adrian Morejon.

The 27-year-old left-hander could earn himself a contract upwards of $90 million this winter, but with all the future money tied up and two owners that paid a large chunk of the $4 billion valluation a few months ago, the question now shifts to how he can be brought back while still having money to allocate around the roster.

The original quote by Musgrove after the NLDS was simple, but there are hundred of different routes that Preller and company can go to retool the team. If the Padres make needle-moving deals this offseason, and perhaps get the kind of offense fans saw post-All-Star break, the 2026-27 offseason could be remembered for years to come.

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