Oct 22, 2026 2:34 PM

With holes in the starting rotation, San Diego Padres' GM A.J. Preller may have to get out new ownership's checkbook to fill them, with Cy Young-winner Tarik Skubal lurking as an expensive possibility.

In MLB, there's a lot of talk about "contention windows," or the number of seasons a team may have to chase postseason glory as currently constructed, but they come in different sizes.

For example, over the past 10 years, the Texas Rangers have had six playoff-less seasons before and three since they won the 2023 World Series, meaning their contention window was about the size of a porthole.

On the other hand, the contention window of the Los Angeles Dodgers - with 14 consecutive playoff appearances and three WS titles since 2013 - best resembles a floor-to-ceiling bay window with a panoramic view of the Pacific Ocean.

When considering the San Diego Padres, their contention window might be similar to a solid double-pane, double-hung model - and it's still open.

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Looking ahead to 2027, the Padres are coming off a record-setting third consecutive playoff appearance with five trips to the postseason in the seven seasons since 2020.

President of baseball operations/GM A.J. Preller - working for the new ownership duo of Jose E. Feliciano and Kwanza Jones - also insists that the team is "all in" as it continues pursuit of that elusive first World Series title.

The foundation is solid with third baseman Manny Machado, centerfielder Jackson Merrill and rightfielder Fernando Tatis all inked to long-term contracts, lights-out closer Mason Miller three years away from free agency, and 20-year-old catching prodigy Ethan Salas tabbed to claim the starting role in 2027.

Where the Padres are short, at this time, is the starting rotation. Walker Buehler, Robbie Ray and Casey Mize are all set to become free agents, while ace Michael King could opt out of the final two years and $58 million of his current deal and the Padres have to decide if they will pick up Nick Pivetta's a 1-year, $14-million club option for 2027. Randy Vasquez is also an option, and he did go 10-6 in 2026, but injuries limited him to 32 games and 23 starts, and he was not asked to pitch in the postseason.

That mound uncertainty - King is expected to opt out and Preller has given no firm indication whether or not Pivetta will be welcomed back - is why, on Tuesday, Tim Kelly of Bleacher Report listed San Diego as one of six teams "that must spend big this offseason in free agency," joining the usual suspects like the Philadelphia Phillies and New York Yankees and some more surprising names like the Pittsburgh Pirates and Athletics.

"Here's one thing you can be sure of: A.J. Preller will always find a way to be aggressive," Kelly wrote while highlighting the Padres' rotational holes. "Perhaps more than ever this offseason, San Diego's president of baseball operations won't have a choice but to be bold."

A good first step would be for Preller to convince King to stay. Since arriving in the East Village in 2024, he has been the rotation's bell cow with a 30-22 record and 3.15 ERA over 432 innings pitched with an average WAR of 3.2.

Preller would also likely welcome Pivetta back. Though he only made eight starts in 2026 because of injury, he did place sixth in the NL Cy Young race in 2025. Buehler could also be asked to return after he led the team with 32 starts in 2026 while compiling a 9-6 record and 4.63 ERA.

Of course, when discussing big spending and free-agent pitching, the elephant - nay, whale - in the room is two-time AL Cy Young Award winner Tarik Skubal, who spent the final two months of the season with Dodgers and is due to hit the open market.

With San Diego's need for starters well known, would Preller make the biggest free-agent splash possible and pursue Skubal?

That question prompted Bleacher Report's Zachary D. Rymer, on Oct. 16, to list the Padres fourth among Skubal's most-likely landing spots behind the New York Mets, Dodgers and Yankees, noting that Feleiciano and Jones have insisted that winning a World Series for the franchise is their No. 1 goal.

"If ever there was a way to show [Feliciano and Jones] mean business, it's by signing Skubal away from those darn Dodgers," he wrote. "Maybe it wouldn't totally undo the little brother vs. big brother dynamic between the two NL West powers, but it would give the Padres a real trump card: the best pitcher in baseball."

Your move, Mr. Preller, and be careful of having that window slam shut on your fingers.

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