Could Chicago Cubs swing a deal for Athletics’ Sonny Gray?

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The Chicago Cubs have made deals involving quality pitchers with the Oakland Athletics before. At the 2014 Trade Deadline, they sent Jeff Samardzija and Jason Hammel to Oakland for Addison Russell, Billy McKinney, Dan Straily and a player to be named later. By all accounts, the Cubs won the trade, as the Athletics lost in the ALDS that year and Russell is now the starting shortstop in Chicago.

The Athletics are rebuilding, and the Cubs are seemingly looking for another pitcher this winter. So could the two match up on a trade again?

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There’s been talk that Oakland could look to deal ace Sonny Gray this offseason and bring in multiple top-tier prospects to jumpstart the rebuilding process. The Athletics farm system took a serious hit when Billy Beane traded a good portion of the team’s prospect depth to acquire parts for the 2014 postseason push, and now find themselves in rebuild mode without the pieces to rebuild.

Chicago, meanwhile, is hardly struggling when it comes to minor-league talent. While top prospects Russell, Kris Bryant, Kyle Schwarber, Jorge Soler and Javier Baez have all already graduated to the big-leagues, McKinney, Albert Almora, C.J. Edwards, Gleyber Torres and Duane Underwood make up just a portion of the prospect bulk that still sits in the Cubs minor league system.

That being said, a deal sending Gray to Chicago for a healthy haul of prospect talent would benefit both Chicago and Oakland. While the asking price on the young righty figures to be steep, the Cubs could match it regardless of position the A’s are seeking.

It’s all but certain that Bryant, Anthony Rizzo and Jake Arrieta would be off limits, and Chicago also seems set on seeing what they have with Schwarber. But Baez, McKinney, Almora, Edwards, Underwood, Dan Vogelbach, Pierce Johnson, Jeimer Candalario and others could all be available in some combination of a package. Major-league ready or near-ready players like Almora, Vogelbach or Baez could appeal to Oakland to help expedite their rebuild, and the Athletics could also go after Starlin Castro and/or Kyle Hendricks if they’re looking for an immediate big-league contribution.

The Cubs, meanwhile, would add Gray to a rotation that already features Arrieta and 2014 offseason signing Jon Lester. Gray’s rookie contract salary also wouldn’t eat into the budget, leaving Theo Epstein and company plenty of financial flexibility to address finding bullpen help, a center fielder and even potentially another starter.

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The Cubs were clear winners the last time these two teams matched up in a deal, but it seems that both sides could walk away beneficiaries this time around. It remains to be seen if the Athletics will ultimately move their prized ace this winter, but Chicago will certainly be in the mix if they do.