This didn't take long. After Gordon Edes broke down why trading Youkilis makes perfect sense, the trade speculation has already been brought up and (unsurprisingly) points the Cubs would be suitors.
From the Chicago Tribune's Phil Rogers:
The Cubs could use Youkilis too, of course. He’s the perfect guy to show a rebuilding lineup how to work a count and would bring a welcome intensity to Wrigley Field. But how many Red Sox-Cubs negotiations can Epstein and Cherington have, anyway? What could the Cubs give Boston that would help the Red Sox make the playoffs? Dempster, maybe. But if the Cubs do trade Dempster or Matt Garza don’t they have to get someone with staying power? Youkilis’ contract pays him $12 million this year with an option for $13 million next year. That’s a lot for any team to pay when it doesn’t have the expectation that he can help it make the playoffs.
While Youkilis may be an ideal veteran for the Cubs, it just doesn't make sense. For a team to get the most out of Youkilis, they would have to make him their first baseman, and for the Cubbies to make that happen, they would have to move their best hitter, Bryan LaHair, to the outfield. This means that Alfonso Soriano or David Dejesus is sitting out and unless they put one of them in that trade, they have to basically eat one of those contracts in order to move them. (And they better not be involved in a Cubs/Sox trade. Neither have hit a home run and they have only driven in 18 RBIs in 226 combined at-bats).
The Sox need pitching but it will take much more for the Sox to get either Dempster or Garza. Dempster is playing out of his mind with a 1.02 ERA (!!!!) in 35 1/3 innings pitched and can probably get two or three good prospects around the trade deadline. Maybe if the Sox pony up,eat Youk's contract ($12 million this season), but after an offseason of penny pinching, it would make no sense for them to do that and take on Dempster and his $14 million dollar salary. The same goes for Garza and his $9.5 million salary and little chance of re-signing him as he'll command a lot of cash in the free agency market.
But Rogers also talks about the other team in Chicago and it is a much better fit:
Kevin Youkilis might be available, and the White Sox have to be interested, for a whole variety of reasons. The biggest of those is that he would take away one of the automatic outs in their lineup, but he could be a good fit contract-for-contract as the Red Sox can use Matt Thornton and, as a bonus, don’t you think Jerry Reinsdorf and Ken Williams would love to stick it to the Cubs and Theo Epstein?
The automatic out Rogers is referring to is Brent Morel, who is hitting a team worst .172. Again, I think Youkilis is a better fit at first but considering the ChiSox are getting nothing from the hot corner and are still in the thick of it in the AL Central, they can roll the dice and see if Youk can play third and stay in one piece. Thornton has two more years on his deal at $5.5 million per year and a team option worth $6 million. He could be the answer to the set up situation, even though he is slowly showing signs of decline (ERA has been rising while his strikeouts per nine innings has been going down the past couple seasons). A risk being taken by both sides to answer one of their biggest problems? Sounds like a fair trade.
This is only speculation and if WIll Middlebrooks continues to rake like he is, it will become a reality very soon.