james shields-chicago cubs-chicago white sox-2018

James Shields offering White Sox unexpected opportunity

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When the Chicago White Sox acquired James Shields from the San Diego Padres on June 4, 2016, the organization was undoubtedly well-intentioned. They thought they saw an opportunity to halt the bleeding and preserve their chances to compete in the AL Central.

Hindsight inevitably proved that to be ill-conceived and time (read: Fernando Tatis Jr.) has only gone on to cast that trade in a lesser and lesser flattering light. We know now that they were never really contenders in 2016 and that deal serves as a reminder of how lacking in self-awareness the front office actually was.

However, flash forward just over two years now and James Shields has provided the White Sox with an unexpected opportunity to recoup some of what they lost. They certainly won’t be getting a player of Tatis’ profile — he’s evolved into the No. 4 prospect in baseball according to MLB.com and is only 19 — but the idea that they can get anything back at all would have been inconceivable just a couple months after the trade.

Shields was bad during that stretch run with the White Sox and then was injured/bad again in 2017. And the four-year, $75 million contract the White Sox inherited when they acquired him made him immovable.

So they entered the 2018 season stuck with a $21 million pitcher stuffed in a minor league contract sack. But Shields has been better than expected and the sure-to-be-selling White Sox may suddenly have a chance to find a market for his services. Especially after twirling seven innings of shutout ball against the Minnesota Twins on Wednesday.

He’s still not playing to that big contract on the whole (he owns a 4.29 ERA and 4.43 FIP), but that’s no longer the bar for the White Sox. The organization knew they were going to be stuck with that contract this season and are financially prepared for that no matter what, so they can eat as much of that deal as needed to try to move him to a starter-desperate contender in the next month and change.

The clock hasn’t struck midnight and Shields hasn’t reverse-Cinderella’d back into a front-of-the-rotation starter. However, he’s been dependable enough this year to be an attractive fourth or fifth option in the right setting.

Even better, the White Sox don’t have to make a thirsty decision just to get rid of him. They know they’re not going to get a major piece back in return for him, so if faced with the prospects of a team simply offering a no-name prospect just to take Shields’ 2019 buyout ($2 million) off their hands, they can keep him if they have to.

Jerry Reinsdorf can afford to pay the buyout himself — or at least posture as if he’s willing to do so to pit any suitors against each other. Because the most desperate team is going to be the one who offers the most and that’s how they maximize value.

Even in that best-case scenario, the White Sox aren’t going to get back a prospect with Major Leaguer (even a fringe big leaguer) written all over him. However, the more desperate they are the more likely it might be that the hypothetical trade partner lets scouting director Nick Hostetler pick through their system to find a guy who he thinks has some hidden potential.

That could be a guy who the White Sox wanted to draft at some point in the last few seasons but weren’t able to select or a player their minor league scouts have identified as underrated. And Tatis himself proves there’s a lot of value in that opportunity.

When the Shields trade was executed, the Padres knew Tatis had potential but even they didn’t know he’d be billed as a future superstar before his 20th birthday. It was Erik Johnson who the Padres assumed would be the key to that trade with Tatis serving as the icing on the cake.

Of course, you shouldn’t expect anybody the White Sox manage to turn Shields into to become a top-five prospect. But it’s certainly possible.

The more realistic expectation is that they just get some piece with some potential down the road. And while that’s still a major loss when weighed against the trade that brought the 36-year-old former All-Star to Chicago in the first place, that’s not what you should be weighing any deal for Shields now against.

That trade was the last bastion of the “all-in” mentality on the South Side. It was the lesson they needed to learn to set them on their current path.

The idea that you could get anything of value for James Shields now is surely gravy.

Ryan Wooden is a full-time sports writer based in the Chicago suburbs. In addition to co-founding The Chicago Sports Column, he is a staffer for SportsLine.com, a premium gambling and fantasy brand from CBS Interactive. Find him away from the computer (or don't) on some body of water or some golf course somewhere.