San Diego Padres: Three biggest questions entering offseason

MILWAUKEE, WISCONSIN - SEPTEMBER 16: Manny Machado #13 of the San Diego Padres walks back to the dugout after striking out in the sixth inning against the Milwaukee Brewers at Miller Park on September 16, 2019 in Milwaukee, Wisconsin. (Photo by Dylan Buell/Getty Images)
MILWAUKEE, WISCONSIN - SEPTEMBER 16: Manny Machado #13 of the San Diego Padres walks back to the dugout after striking out in the sixth inning against the Milwaukee Brewers at Miller Park on September 16, 2019 in Milwaukee, Wisconsin. (Photo by Dylan Buell/Getty Images) /
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San Diego Padres
(Photo by Mike Stobe/Getty Images) /

Will the San Diego Padres acquire a frontline starting pitcher?

It’s the money question that fans will be waiting for all winter. Will A.J. Preller pull the trigger on a frontline starter to lead a young rotation that is going to be filled with very talented but inexperienced arms?

Gerrit Cole is the big fish this offseason and he has been rumored to want to play in Southern California and the Padres fit that description.

Along with Joe Maddon and the Los Angeles Angels, the Padres could be in on the bidding but their huge contracts of Manny Machado, Eric Hosmer, and Wil Myers would complicate things.

Myers would have to go if they would want any chance at getting Cole, who is going to want around $300 million in free agency.

So, let’s assume that Cole is out of the question.

Madison Bumgarner, Zack Wheeler, and possibly Stephen Strasburg are out there.

Strasburg seems like the obvious choice because he dominated at San Diego State but it is also most likely that he just restructures his contract and just signs with the Nationals again.

With that said, A.J. Preller’s best route would be by trade. Corey Kluber could become available again and San Diego has expressed interest before. With an abundance of prospects, I think their best route is to trade for a starter.

The next question is involving one of their former All-Stars…