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Come Fan with UsFriday, June 26, 2026

A Brief Examination Of Edwin Jackson’s Trade History

Edwin Jackson has been traded a whole bunch of times. Might this in some way help to explain why his market as a free agent was seemingly so slow to develop?

ARLINGTON, TX: Edwin Jackson #22 of the St. Louis Cardinals pitches during Game Four of the MLB World Series against the Texas Rangers at Rangers Ballpark in Arlington in Arlington, Texas. (Photo by Tony Gutierrez-Pool/Getty Images)
ARLINGTON, TX: Edwin Jackson #22 of the St. Louis Cardinals pitches during Game Four of the MLB World Series against the Texas Rangers at Rangers Ballpark in Arlington in Arlington, Texas. (Photo by Tony Gutierrez-Pool/Getty Images)
ARLINGTON, TX: Edwin Jackson #22 of the St. Louis Cardinals pitches during Game Four of the MLB World Series against the Texas Rangers at Rangers Ballpark in Arlington in Arlington, Texas. (Photo by Tony Gutierrez-Pool/Getty Images)
Getty Images

Thursday afternoon, reports emerged that Edwin Jackson had found a home. Finally, free agent starting pitcher Edwin Jackson had found a home. The Washington Nationals announced that they were signing Jackson to a one-year contract, and they made the announcement even before Jackson passed a physical. Thursday was the second day of February. Spring training begins in just a few weeks.

Jackson took a long time to sign, because Jackson’s market was slow to develop. At least, from the outside, it appeared as if Jackson’s market was slow to develop. We can never know for sure what things were really like. That Jackson signed for a year and about $10 million when he entered the offseason looking for something much longer and bigger suggests as much.

Why did this happen? Why wasn't there greater demand for a pitcher of Jackson's proven caliber? One response could be "well Roy Oswalt's still a free agent and Prince Fielder only recently signed so sometimes things just happen this way." Another response of which I saw a lot was "Jackson's been traded a bunch of times, indicating that there's something about him they see that we're missing."

Or something along those lines. Basically, I saw a lot of people trying to explain Jackson’s market by pointing to his trade history. Jackson’s been a pretty good pitcher. He’s been traded unusually often. Therefore, Jackson has some problem that must be known within baseball circles.

What I’ve decided to do here is try to see whether this theory holds up. I’m going to re-visit each of the Edwin Jackson trades. I’m probably not the first person to do this. In fact, I’m almost certain I’m not the first person to do this. This is a pretty obvious idea. But it’s an idea I’m going to pursue, and if you or someone you know has pursued it too, then the more the merrier! Let us all overlap like so many happy Venn diagrams!

January 2006
Dodgers trade Edwin Jackson, Chuck Tiffany to Devil Rays for Danys Baez, Lance Carter

In retrospect, this one almost hurts to look at. Danys Baez and Lance Carter. Jackson, of course, was one of the Dodgers’ top prospects. Why make this trade?

Well, Jackson was one of the Dodgers’ top prospects, but his stock was plummeting. In 75⅓ major league innings, he had 39 walks, 48 strikeouts, and a 5.50 ERA. The two previous years in triple-A, he threw 146 innings, with 92 walks, 103 strikeouts, and a 6.90 ERA. What Jackson had on his side was stuff and youth. What he didn’t have was performance.

So the Dodgers sold low, but Jackson hadn’t done anything in a couple years. Baez was a proven closer. Carter was a potentially useful reliever. New GM Ned Colletti wanted to build an instant winner. All this trade was was a mistake.

December 2008
Rays trade Edwin Jackson to Tigers for Matt Joyce

The Dodgers sold low on Jackson. The Rays sold high. Jackson was coming off a season in which he posted a 100 ERA+, but that year he also posted unimpressive peripherals. The Rays saw an opportunity, dealing Jackson to not only open up rotation space for David Price, but to also bring in a talented young outfielder with several years of team control. Joyce had just broken in with the Tigers and posted a 115 OPS+ over nearly 300 trips to the plate. He played solid defense and had hit well in the minors.

This trade isn’t evidence that the Rays were dissatisfied with Edwin Jackson. This trade is evidence that the Rays recognized that Jackson might be overvalued, so they cashed him in.

December 2009
Tigers trade Edwin Jackson to Diamondbacks, Curtis Granderson to Yankees for Austin Jackson, Max Scherzer, Phil Coke, Daniel Schlereth

The explanation here from the Tigers’ perspective was all about salary reduction. Jackson and Granderson were good players, but they were good players set to start getting expensive. The other Jackson and Scherzer, meanwhile, were talented and practically babies. Edwin Jackson was coming off a solid, breakthrough season, but there was reason to believe that Scherzer was better, and younger. There was excellent reason to believe that Scherzer was younger. The Tigers gave up value, and the Tigers got cheaper value.

July 2010
Diamondbacks trade Edwin Jackson to White Sox for Daniel Hudson, David Holmberg

When the Tigers traded Jackson, they traded him after he did well. Jackson didn’t do so well with the Diamondbacks. At the time of the trade, his ERA stood at 5.16, and his strikeout-to-walk ratio was mediocre. Additionally, the Diamondbacks were 38-65 and looking to shed, and Jackson was a year and a half away from free agency. Arizona picked up two pitchers, one of whom was an excellent prospect. Hudson has developed quite nicely and is under team control for a long time.

July 2011
White Sox trade Edwin Jackson, Mark Teahen to Blue Jays for Jason Frasor, Zach Stewart

The White Sox were hovering around .500 and flirting with contention. They were also using a six-man starting rotation. Jackson had good numbers but was months away from becoming a free agent. Chicago turned him in for bullpen help, a moderately promising pitching prospect, and salary relief, as Teahen was due $5.5 million in 2012. That the White Sox were able to shed that salary should not be ignored.

July 2011
Blue Jays trade Edwin Jackson, Corey Patterson, Octavio Dotel, Marc Rzepczynski, cash to Cardinals for Colby Rasmus, Trever Miller, Brian Tallet, P.J. Walters

This trade had a lot of parts to it, but at its core, it was Edwin Jackson for Colby Rasmus. The Blue Jays got Jackson and flipped him immediately, the same way they did Mike Napoli several months before. The idea was that they could get a potential franchise center fielder while his value was low. They didn't need a starter rental in Jackson. The Cardinals were happy to get Jackson as they had playoff aspirations.

That’s a review of the trades. Each and every one of them can be explained pretty reasonably. There’s little hint that there was something about Edwin Jackson that grew to rub teams the wrong way, except occasionally for bad performance. That teams were able to trade Jackson for value suggests demand, which suggests that Jackson doesn’t have some negative reputation within baseball circles. Word about that stuff gets around in a hurry.

I'm sure teams realize that Jackson could be more than he is, given the quality of his raw stuff. It's possible that pitching coaches get excited about the prospect of working with Edwin Jackson, and then frustrated over time when he doesn't make the leap. I don't know, I'm not a pitching coach. But I don't think that Edwin Jackson's trade history should be held against him. You could look at it as a sign that he's in some way undesirable, but you could just as easily look at it as a sign that he's highly desirable. Look at all of the teams that wanted Edwin Jackson!

Here’s a shot in the dark as to what Edwin Jackson’s reputation is within baseball circles: talented, valuable pitcher who’s less than his stuff. I don’t think there’s anything more sinister than that, and I don’t think Jackson’s trade history is compelling evidence of anything more sinister than that. Teams are very much aware of his value, and I suspect his market was slow to develop due to a combination of an unusual overall market and the Boras factor. But I’ve been wrong before. Like a whole bunch of times.

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