The Many Moves of Edwin Jackson: Baseball's ultimate chess piece journeys toward history

As he returns to the major leagues with one of the 12 teams he's already pitched for, Jackson reflects on a life and career that have often gone up, done and even sideways.

SYRACUSE, N.Y. -- For the third time in the past week, ever since his baseball career landed at its latest—and geographically northernmost—outpost, Edwin Jackson was just encouraged to write a book. Apparently the idea is already taking hold. “I might need to get started,” he says. “As much as I’ve been through, I could’ve had a nice little journal right now. I could’ve had an editor already working. Or maybe I’ll take a month of just talking into a recorder—a story about every team.”

At first Jackson suggests the working title, Life of a Rolling Stone, but quickly concludes that Mick and Keith and the band would object on the grounds of copyright infringement. So he pauses to think. It’s a drizzly afternoon in late June, several hours before the Syracuse Chiefs, the Triple A affiliate of the Washington Nationals, host the Scranton/Wilkes-Barre Railriders. As Jackson lounges in the home dugout at NBT Bank Stadium, wearing some slick camouflage leggings and a flat-brimmed cap that seems to hover above his hair, fellow Chiefs pitchers trickle onto the field for pregame stretches. At 33, Jackson is the second oldest of the group. He has also thrown more major-league innings than the rest combined.

“The Life of a Chess Piece,” he finally says. “There you go. Because that’s what we are.”

And no active player has hopscotched around the board more often than Jackson. “LA to Tampa Bay to Detroit to Arizona to Chicago, from Chicago to St. Louis, then to D.C.,” he says, no sweat. “D.C. to Chicago--this time for the Cubs--to Atlanta, to San Diego, to Miami, to Baltimore…”

On June 7, the righthander entered from the Orioles’ bullpen and began the seventh inning with a 92 mph two-seamer against Pirates outfielder Gregory Polanco. At that moment, Jackson reached history’s doorstep: By appearing for his 12th different MLB club, he officially moved one shy of matching former pitcher Octavio Dotel’s all-time record. In 15 years, Jackson has dressed for eight franchises in the National League and four in the American League, spanning five of MLB’s six divisions. Among active players, pitchers Bartolo Colon, Jason Grilli and Chad Qualls come closest . . . at nine apiece. Add up all of Jackson’s teammates and you get enough bodies to staff 27 different 25-man rosters, with three to spare.

“Sometimes you’re just a pawn, man,” he says. “I’ve been traded after bad years. I’ve been traded after a 14-win season. Sometimes it doesn’t even matter what you do.” Other times Jackson has felt like the king. On his 20th birthday, Sept. 9, 2003, he debuted for the Dodgers and beat Randy Johnson in Arizona. As a Ray in 2008 he led the team with 14 wins as it stunned baseball by reaching the World Series. As a Tiger he made the 2009 All-Star Game, where he efficiently recorded three outs on four pitches to help the AL to a 4-3 win. The next year he tossed a no-hitter for the Diamondbacks against the Rays in which he threw 149 pitches, still the highest single-game total by a pitcher in the past 14 years. (“All that means is I really stacked the deck against myself.”) In 2011 he he won the World Series as a Cardinals—fittingly enough with Dotel as a teammate.

“Hey, you can be everything,” he says. “A pawn, a king, a knight.” Two spaces up and one over, able to move forward, backward, left, right—certainly the knight is valuable. Six days after his Orioles debut, Jackson was designated for assignment and released. According to his agent, Omar Bradford, Jackson fielded opportunities to match Dotel’s career mark. Instead, he broke new personal ground by returning to an organization for the first time, signing a minor-league deal with the Nats. “First repeat offender,” he says, smiling wide.

So far, Jackson has made good on his decision. After carrying a 17 1/3-inning, four-hit scoreless streak with Syracuse into the All-Star break, he earned a promotion to start for Washington on Tuesday in Anaheim. It will be Jackson’s first MLB start since September 2016, back when he played for the Padres, which means prospective publishers should be notified about an updated word count. “He probably could write a book, honestly,” says Tigers outfielder Justin Upton, a close friend and former teammate. “Stories for days.”

But where to begin?

“Man,” Jackson says, “I guess if I was going to write something, I’ve got to go back to high school.”

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As the national crosschecker for the Los Angeles Dodgers, tasked with filing follow-up reports around the country, Jimmy Lester rarely found time to watch the local team less than three miles from his home in Columbus, Ga., located near the Alabama border. Heading into the 2001 draft, the top prospect at Shaw High School was Nick Shore, a pitcher who eventually went in the fourth round to the Expos. “That was the guy everyone wanted to see,” Lester says. But Shaw’s head coach, Charles Flowers, kept bugging him about someone else, an outfielder whom Flowers kept calling, “my sleeper.”

That June, Los Angeles drafted Jackson in the sixth round, 190th overall, but wondered whether to put him on the mound or in the outfield. After all, he had only started during his senior season at Shaw, and even then was still learning how to pitch. For a time the Dodgers let him hit during instructional league. Then the scouting director visited, clocked Jackson’s fastball around 94 mph, and told Lester, “He ain’t hitting anymore. He’s a pitcher.”

The Dodgers saw his raw talent as moldable, and Jackson was an eager pupil. He reached the majors just 27 months after getting picked and promptly out-dueled the Big Unit. Before the 2004 season, Baseball America ranked him as the fourth-best prospect in the game. Perhaps poised to become the Dodgers’ next great homegrown pitcher, Jackson was instead packaged to the Rays in January 2006. “It wasn’t a big deal the first time I got traded,” he says. “It was, well, onto the next journey. Everybody handles change different. For me, it’s never really been hard.”

G Fiume/Getty Images

As a kid, Jackson had no choice but to adapt. He was born in Germany, the son of retired Army sergeant Edwin Jackson Sr. Before age 7, his family had moved to Louisiana, returned to Germany and finally settled at Fort Benning in Georgia. “Being on the move, it’s all I know,” Jackson says. “Life out of a suitcase. It’s like I was predestined for this.”

Certainly Jackson can attribute some of this adaptability to his military background. But he’s also a naturally joyous soul, armed with diverse musical tastes that make him the perfect clubhouse deejay. He’s also been known to hurl some creative trash talk at the card table but is always quick to let rookies borrow his truck for trips to the store. “Whether it’s Latin, black or white,” says Melvin Upton Jr., Jackson’s former roommate and teammate in the Tampa Bay organization, “everybody’s always loved him, no matter what team he’s been with.”

Which doesn’t quite jibe with Jackson’s résumé, at least to the uninformed eye. “That was the rap for a while,” he says. “What are you doing to people? What’s the deal? Why are you on so many different teams? I’ve had people tell me, ‘I assumed you were an a------,’ until I actually got there.”

But no one draws paychecks from 40% of the league by being a bad teammate. “From the outside looking in, the natural response is, ‘Oh, he may not be a clubhouse guy,’” Justin Upton says. “That’s not the case at all.” In fact, the All-Star outfielder adds, “Some of the stuff he’s been through, he’s one of the only people I know who could handle that.”

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It wasn’t always easy. As a cargo train rumbles east beyond the outfield wall, Jackson lifts his shirt and reveals a quote from Martin Luther King Jr., inked in large cursive on his left oblique: “The ultimate measure of a man is not where he stands in moments of comfort and convenience, but where he stands at times of challenge and controversy.”

Each piece of artwork on Jackson’s body holds meaning. There are footprints from the births of his two children, Exavier and Elan. A pair of dice cast to 3 and 6, the jersey number he wore for six MLB team and sported in Syracuse. The first tattoo was the biggest, a cross adorned with initials of family members and wrapped in rose thorns, dripping both blood and water. Another two—the MLK quote and the phrase “By any means necessary,” which runs along his collarbone—remind Jackson to stay positive “when s--- hits the fan,” he says.

Not coincidentally, he got both of these while playing for the Cubs.

Already seven teams deep and fresh off his first tour in Washington, Jackson hit paydirt by signing a four-year, $52 million contract with Chicago on Jan. 2, 2013. The term was supposed to give Jackson some stability, especially after deadline trades in both '10 (D-Backs to the White Sox) and '11 (White Sox to the Blue Jays, who promptly flipped him to St. Louis). Instead Jackson went 16-34 with a 5.37 ERA in two-plus years, team president Theo Epstein called the signing “a mistake” to season-ticket holders and the Cubs released him in July of 2015. “I lost 18 games one year,” Jackson says, remembering 2013 more matter-of-factly than mad. “I could try to blow 18 games on purpose, throw balls right down the middle, and still get outs.”

Around that time, Jackson was beginning to start a family. He first met Erica Zanders when he was in the Dodgers’ system, at a bar near Montgomery, Ala., where she was stationed with the Air Force and his relatives lived. He proposed when he played for the White Sox, postgame in Anaheim, and they married two days after he signed the Cubs contract, at a ceremony officiated by former MLB outfielder Chris Singleton. She’s packed up rental houses and rushed to new cities, two children—a third is due this November—in tow.  “It’s always a s--- show,” she says, calling from the Homewood Suites in Syracuse. “But we make it work.”

A former air traffic controller with overseas service stints in South Korea and Dubai, Erica Jackson has actually hopped around more than her husband; she’s never lived anywhere longer than five years. But even she admits that Edwin handles change better: “He’s very go-with-the-flow. His mentality, which he tries to emphasize to me, is that worrying won’t help. A couple times—and I say a couple, maybe two—he came home and he was pretty upset about a game where he gave up a bunch of runs, and he yelled off the balcony. That was it.”

*****

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Over a lengthy chat in the Chiefs’ dugout, Jackson doesn’t break from his default calm. “At this point,” he says, “everything from here is a bonus. Made my money, got a World Series ring, right now it’s just about having fun—having fun and getting back to the big leagues, and hopefully seeing if we can win another ring somewhere. I’ve got 10-plus years in. Have fun, stress-free. When I’m tired of it, then I’ll retire.”

That day isn’t coming soon. After allowing one run and striking out 22 in 20 1/3 innings with the Chiefs, Jackson earned a promotion to replace Nationals starter Joe Ross, who needs Tommy John surgery. According to the Washington Post, Jackson could have opted out of his contract and sought work elsewhere if he hadn’t reached the majors by Aug. 1. Instead, one of baseball’s greatest gadabouts returns to D.C., which he calls “one of the places I feel like I’m at home.”

Can Jackson break Dotel’s record? His friends think so. “With his knowledge, as many games as he’s pitched in, what he’s been through, he’s got the capacity to do anything he wants,” Upton Jr. says. “I’m calling that he pitches until he’s 40.” For context, Dotel needed until age 38 to hit a baker’s dozen; pitcher Mike Morgan and hitter Matt Stairs each reached 12 in their 40s, and Ron Villone joined them at 39. Jackson meanwhile turns 34 this September and has never had a major injury.

Does Jackson care? In his mind, that particular topic isn’t worth spilling much ink. “If it happens, it happens,” he says with a shrug. “If not, then hey, it wasn't meant to be.

“Ride the wave, man. It’s like you’re in the ocean. You can’t swim against the current. Flow with it, and see where it takes you. That’s life.”