Edwin Jackson has had one of the more interesting baseball careers. Given how many different teams he's played for in his 12 parts of seasons in the majors, he might choose a different adjective, though.
In the early to middle 2000s, Jackson was one of the best pitching prospects in baseball, topping out as Baseball America's #4 prospect in 2004, and was in the top 100 2003-2005. He debuted as a 19 year old for the Dodgers in 2003, but never managed to crack their rotation in his other two seasons there, never accumulating 30 innings. Thanks to an impressive amount of roster mismanagement, burning options in those years, the Dodgers needed to either put Jackson on their major league roster or lose him to waivers. Instead, the Dodgers traded him for two mediocre relievers, Danys Baez and Lance Carter, and Jackson found himself headed to the Tampa Bay Devil Rays, who were still a baseball laughing stock.
The (then) Devil Rays eased Jackson into the majors, giving him another 36 innings as a middle reliever in 2006, before having him in the rotation full time for 2007 and 2008. These three years in Tampa, Jackson established himself as a bit of a baseball enigma. In 2007 and 2008 he was a rotation stalwart, making 31 starts both seasons, but he always seemed to underperform his mid-nineties fastball that topped out close to 100 miles per hour. A moderately successful 14-11 record with the (now) Tampa Bay Rays in 2008 masked the fact that his strikeout rate had dropped precipitously and his walks had substantially increased; in 2007 he was unlucky, going 5-15, despite solid strikeout and walk rates, but in 2008 he seemed to be getting by on smoke and mirrors. Fed up with his inconsistencies, the Rays shipped him to Detroit, receiving then prospect Matt Joyce in return. In a similar move, they also took on frustrating starting pitcher Matt Garza from the Twins, in exchange for the equally frustrating Delmon Young.
This began a spectacular series of shifting, impermanent stays for a successful major league player. Jackson, still arbitration eligible, signed a $2.4 million deal with the Tigers, and built on his 2007 numbers, putting up what would become typical Edwin Jackson numbers. He struck out about 7 batters per nine innings, walked about 3, and eeked out a 3.62 ERA, which was a bit lucky this year. Still averaging a mid-ninties fastball that touched 99, the Tigers clearly were not happy. With center fielder Curtis Granderson about to leave as a free agent, they completed a massive, three-way trade with the Yankees and Diamondbacks to re-tool on the fly, acquiring players who would become foundations for the recent success of the Tigers: center fielder Austin Jackson and reliever Phil Coke from the Yankees, and starting pitcher Max Scherzer from the Diamondbacks. Edwin Jackson would head to Arizona in the deal, with Granderson heading to New York.
The Diamondbacks quickly signed Jackson to a two year, $13.5 million deal to buy out his last two years of arbitration. The Diamondbacks expected to contend quickly, and were trying to retool on the fly by adding two starters, Jackson and former Yankee prospect Ian Kennedy. Both hadn't yet lived up to their potential, but with budding superstar Justin Upton holding his own in the majors at 21, the Diamondbacks thought they were about to start a championship window and needed the arms to compete. Very quickly, it was clear that things were not working out for Jackson in Arizona. Walks were up, strikeouts were down again, mirroring his poor peripherals in his last year in Tampa; that was two teams and two major trades ago, but only a year and a half had elapsed.
After less than a year in Arizona, only five and a half months after signing his two year contract extension, Jackson was on the road again. This time, the trade was not a blockbuster; Jackson, and his now burdensome contract, was shipped to the Chicago White Sox, part of a spectacular summer of feckless spending where Chicago GM Kenny Williams also took on Jake Peavy's even more toxic $50 million commitment in the hopes of making the playoffs with their 58-45 record on July 31, 2010, and a razor thin half game lead over the Twins. The White Sox crumbled in the second half, going 30-29, while the Twins played great baseball and comfortably won the division by 6 games. Peavy failed to be the ace the White Sox were hoping for, going 7-6 with a pedestrian 4.63 ERA. Jackson, however, was a revelation. Despite still pitching in a hitters park in Chicago, Jackson put up some of the best numbers of his career a 3.24 ERA and a 1.21 WHIP, all backed up by excellent strikeout and walk rates (77 and 18, respectively, in 75 innings). Had Jackson finally put it all together? After all, he had just turned 27 and still threw his mid-nineties fastball. Also, had he finally found a home in Chicago?
Well, you can probably guess the answer is no. Jackson was still an above average pitcher for the White Sox in 2011, but as in previous "breakouts", the following year his strikeouts decline and his walks crept back up. A serviceable 3.92 ERA masked a bloated 1.42 WHIP, a sign of future trouble to come, unless something changed. With the White Sox a game under .500 and 3.5 games behind the Tigers, Jackson was traded to the Toronto Blue Jays essentially for salary relief - reliever Jason Frasor and low level pitching prospect Zach Stewart, another player whose numbers never matched their stuff, and has since been traded from the White Sox to the Red Sox in the Kevin Youkilis trade in 2012. Jackson's time in Toronto was short, however. In fact, it was less than a day. Almost immediately after trading for Jackson, Blue Jays' GM Alex Anthopolous flipped Jackson and other pieces for disgruntled center fielder Colby Rasmus. Unlike in 2011, a change of scenery did not improve Jackson's results; he continued posting a slightly above average ERA without backing it up, although the Cardinals completed one of the most unlikely regular season comebacks, leading to a World Series championship. Despite being a member of the starting rotation throughout the playoffs, the Cardinals let Jackson walk following the 2011 season, presumably because they could not meet his free agent demands.
Despite his up and down career, Jackson was still expected to sign a lucrative contract of three to four years for $30-$50 million. Somehow, that contract never materialized. Jackson, and "super agent" Scott Boras, massively overplayed their hand, turning down several multi-year options before finally settling for a one year, $11 million deal from the Nationals. Jackson had another solid, if unspectacular season for Washington this year, putting upa 4.03 ERA and a 1.22 WHIP with decent peripherals. Jackson is entering a similar market to last year, except for a couple significant differences. First, he fired Boras midseason; given how poorly his negotiations went, and how much guaranteed money. Second, there is a glut of arms on the market this year, with Brandon McCarthy, Anibal Sanchez, Shaun Marcum, and Hiroki Kuroda among the second tier options, not to mention potential aces like Dan Haren, Jake Peavy, or Zach Greinke. Given these two factors, Jackson may again end up with a deal less than the prognosticators think he'll get.
If his price does fall, he could be a solid bargain for the Red Sox. Edwin Jackson has been traded so many times in his career, and invariably there are whispers about his role as a teammate. That might not be a great fit with the Red Sox, given their current climate, but their is one huge thing Jackson has going for him - durability. Since he became a full time member of the Devil Rays' starting rotation, Edwin Jackson has made 30 or more starts in every single one of his major league seasons, good for 9th in baseball since that time. And he's been at least a 2.7 win player in each of the last four years. You know who else can match that number of starts since 2007 and that consistent production? Justin Verlander, Felix Hernandez, CC Sabathia, and Matt Cain. That's a far cry from the uncertainty surrounding the infamous AL East free agent busts John Lackey and AJ Burnett.