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1. Phillies trade Ryne Sandberg to Cubs
This one is easy to gape at in retrospect, of course, and if hindsight alone condemned it, that wouldn't be enough to call it shocking. Teams trade youngsters all the time and every now and then those youngsters grow up to be Hall of Fame candidates: John Smoltz, Jeff Bagwell, et al. And many, many bad trades look fine at the time of their announcement. Who is going to win the Donaldson-for Lawrie-et-al deal? We may not know for a while, and it will be easy to call it shocking if it ends up lopsided; right now, it's defensible for either side.

But the Phillies' January 1982 trade of Ryne Sandberg to the Cubs for Ivan DeJesus was weird even at the time, and hard to defend. Sandberg was blocked at shortstop by Larry Bowa, but Bowa, with whom the Phils were in a contract dispute, was also traded to the Cubs. In return, Philadelphia got Ivan DeJesus. DeJesus had been a pretty good shortstop in the late 1970s but then declined rapidly and bottomed out in 1981, "losing" the Triple Crown in that strike-shortened season, as memorialized by the folks at Razzball: he finished dead last in the league in batting average, home runs and RBI–(!!!)–while playing all 106 games and batting leadoff in 59 of them—(!!!). The Phillies traded two valuable shortstop commodities for one basically worthless one.

There must have been some rational thinking behind this deal. If you have insight into that thinking, please let us know what it was! —Adam Sobsey

2. Blue Jays trade Vernon Wells to Angels
There are the milestones that define our lifetimes, and there are the watershed moments that define our team fandom—the moments where we remember exactly where we were, how we reacted, and who we called first. Is that too dramatic? Perhaps it is. When Alex Anthopolous offloaded Vernon Wells’ $80 million contract, the contract that ended just this September, I yelled. I yelled, a little too loudly in the small Vietnamese restaurant I was dining at with my baseball-agnostic freshman roommates. Whoops.

It was the trade that ignited Anthopoulos’ “ninja reputation” of dropping unsuspecting deals on the baseball community without rumor lead-up. It was the trade that freed up cash to extend Jose Bautista a month later. It was the trade that let the Jays compete now rather than later, unburdened by Wells’ cinderblock. Thanks, Tony Reagins. —Andrew Koo

3. Mariners trade Ichiro Suzuki to Yankees
When a player becomes synonymous with his organization, it's always a little shocking when that player is then traded to a competitor. Ichiro Suzuki was, for the first 11 1/2 seasons of his career, the singular representation of the Seattle Mariners franchise in many a fan's head. That's why the July 23rd, 2012 trade that sent Ichiro to the Bronx was particularly jarring.

Sure, there was a lot more at play here. The Mariners had lost 196 games over the prior two seasons and were on pace for another losing campaign when the trade deadline came around. The team was in the midst of a rebuild, and Ichiro's best days were behind him. Heck, the outfielder even asked the organization to consider sending him to a competitor.

I'd like to believe that Ichiro's trade request was just as the team's CEO characterized it: a mutually beneficial opportunity. Mariners' CEO Howard Lincoln said, "Several weeks ago, Ichiro Suzuki, through his long time agent, Tony Attanasio, approached Chuck Armstrong and me to ask that the Mariners consider trading him. Ichiro knows that the club is building for the future, and he felt that what was best for the team was to be traded to another club and give our younger players an opportunity to develop." Obviously it was nice for Ichiro to go to a contender and play out the rest of that season with playoff aspirations. I'm sure that played a large part in his decision. Ichiro seems like a nice man though and I'd like to, at least in some small way, hope that he did in fact have the team's best interests at heart in making the request. Not because he owed the Mariners anything (far from it), but because it would show what a selfless person he is. It might be silly to hope that a professional athlete would operate in anything but his own best interests, but there it is.

After getting over the initial shock of the trade my favorite part came in Ichiro's uniform number selection. Ichiro opted to not take number 51, the one he had worn in Seattle, out of deference to Bernie Williams the last Yankee to don that number in Pinstripes. Now you can see why I kind of hope that Mr. Lincoln's account was a part of Ichiro's decision-making.

I will always think of Ichiro as a Seattle Mariner. I was genuinely shocked when the Mariners traded him to New York. Not because it was an illogical move or because of any on-field reason. Just because to me, they may as well have traded the Space Needle itself to New York. —Jeff Long

4. Rangers trade Juan Gonzalez to Tigers
The full trade actually went like this: Rangers trade Juan Gonzalez, Danny Patterson, and Gregg Zaun to the Tigers for Justin Thompson, Gabe Kapler, Frank Catalanotto, Francisco Cordero, Bill Haselman, and Alan Webb

In what can only be considered a Shakespearean catharsis, Tigers general manager Randy Smith was tired of being a losing team so he decided to trade for, I guess, a baseball player someone has heard of, give up a bunch of young guys for it, and that is how you win championships?

Gonzalez won two MVPs and dinged about 40 homers a season in the cozy Rangers ballpark, but suddenly had difficulty launching anything past those far walls in the newly-erected Comerica Park, so he left in free agency to have a bounce-back year in Cleveland, of all places. This meant Patterson, who stayed through the end of his career in 2004, ended up producing more WARP than Gonzalez. The third player Detroit got, Gregg Zaun, was then flipped to Kansas City for–nobody's sure—maybe a clean pair of pants. Patterson even outlasted Smith, the mastermind of the trade, who was fired in 2002.

Yes, the Rangers won the trade, but the blast radius of their return crop also was puzzling. Thompson, a former All-Star pitcher, never recovered from arm surgery. Cordero carved out a nice 300-save career. Catalanotto continued to exist. Kapler, I think, became a writer? Haselman was the only player over 25 the Tigers were willing to part with. Webb never reached the majors and for all we know could have been a clerical error. —Matt Sussman

5. Red Sox trade Stephen Drew to Yankees
The last time Boston and New York made a trade, the Red Sox wound up with Pedro. The year was 1997 and the Red Sox were on the way to 78 wins and a date with mortality. The Yankees were in the midst of a 96-win season that would ultimately see them lose the Division Series to the Cleveland Indians, who would go on to lose in the World Series to the Florida Marlins, who would go on to trade their entire team. Ain’t life grand? But yes, 1997: The Yankees wanted Mike Stanley from the Red Sox and the Red Sox obliged. In return they received a packaged headed by pitching prospect Tony Armas. Six months later Boston shipped Armas to Montreal with Carl Pavano for Pedro Martinez and five years later won the World Series for the first time in pretty much everyone’s lifetime. So that didn’t end up working out for New York.

Understandably, 17 years passed.

During that time the Red Sox made trades with every team in baseball except the Yankees. During that time the Yankees made trades with every team in baseball except the Red Sox. The two were perpetually on opposite sides of the cafeteria, an expansive portable dance floor and the sounds of Scott Stapp’s solo album dividing the parties like North America divides the Pacific from the Atlantic. There may have been cross-room glaring, there may have been longing stares that just missed catching the other’s eye. There may have been utter indifference. But no matter what, 17 years crawled by.

Then, last year, the Red Sox re-signed Stephen Drew mid-season and he was awful at the plate, just goat-bites-your-daughter’s-nose-off-at-a-petting-zoo awful. Somehow Drew’s hideous hitting didn’t serve to elevate the Red Sox from their stupor and, with Xander Bogaerts’ development the only useful bit to salvage of a lost season, Drew’s defense became superfluous. At the same time, 215 miles to the southwest [cue Batman music], the Yankees plans to start Brian Roberts at second base all season long had hit a snag. That snag was called ‘Brian Roberts is always terrible or injured’ which should be an off Broadway production featuring lots of emotive music (“Whyyyyy am I soooo terrible? [pause] Ouch.”). With Derek Jeter’s defense resembling a Derek Jeter bobblehead placed gently on the right side of the infield (“Past a bobbling Jeter!”) The Yankees needed an upgrade to their middle infield.

Everyone thought there was a good match for a trade, but I’m not sure anyone was thinking that it would actually happen. The fit was perfect, but could the two teams overcome 17 years of cold war stalemate?

Yes.

Surprise. —Matthew Kory

6. Marlins trade Jose Reyes, Mark Buehrle, and Josh Johnson to Blue Jays
In the months leading up to November 19, 2012, the Miami Marlins hadn’t exactly been swimming in positive press coverage. Not that the team did anything to deserve otherwise: Aside from handing Adam Greenberg a token plate appearance at the end of a monumentally disappointing season, the Fish bungled everything. There were free agent flops, insensitive remarks, and false proclamations about attendance, all in front of paltry crowds in Miami’s tacky and taxpayer-funded ballpark. They even got a Passan special after a midseason fire sale sent Hanley Ramirez, Ricky Nolasco, and Omar Infante out of town.

But nothing could have prepared the Marlins for the blowback they received after shocking the baseball world by sending Jose Reyes, Mark Buehrle, and Josh Johnson to Toronto for prospects. In the trade, the Marlins shed over $200 million in future payroll but also unloaded three of their most talented players less than a year after a spending spree supposedly announced the dawn of a new era in Miami. Instead, Marlins fans were treated to a $39 million payroll and 100 losses in year two of Marlins Park.

Despite the shock value, Miami’s baseball people insisted that the trade was made to help solidify the next good Marlins ballclub, an argument that only looks better with time. At the very least the Marlins received a starting shortstop and a mid-rotation starter while freeing up money to help cover other deficiencies. Whether the club actually spends that money—Giancarlo Stanton extension aside—remains to be seen. What is clear is that the unexpected swap radically altered the courses of the two franchises involved in one of the more interesting deals of the decade. —Brendan Gawlowski

7. The White Flag trade of 1997
I guess back in 1997, every trade shocked me. You never heard rumors, never knew who was available; I’m not totally sure that I knew that July 31st, 1997 even was a trade deadline. But the Giants were in first place by a half game at the time, and they acquired Wilson Alvarez, Roberto Hernandez and Danny Darwin—a playoff-caliber starter, a playoff-caliber closer, and a swingman whose face was on no fewer than about 600 baseball cards I owned—for the pennant run.

This trade is remembered as shocking not for what it ultimately meant for the Giants—of the three, only Hernandez was any good, and they combined to allow seven runs in seven innings during an NLDS sweep—but for what it meant at the time for the White Sox. This was the famous White Flag trade; Chicago was only three and a half games out of first at the time. The team ahead of them, the Indians, seemed so much better, having won 99 games the year before, but they’d win the division (and go to the World Series) with only 86 wins in 1997. Surely the White Sox could have aspired to that. "I've never seen in my 22 years in baseball an owner say that he was giving up on his ballclub,” Darwin said. “Anyone who thinks this White Sox team can catch Cleveland is crazy,” Jerry Reinsdorf said.

Nobody in Chicago ever really forgot that trade. Five years later, it was being half-heartedly spun as a victory (because Keith Foulke, among the six prospects Chicago received, turned into something). When the Giants and White Sox played in interleague action this summer, the White Flag trade served as the news hook.

But it wasn’t shocking to me at the time because of the White Sox. It was shocking because at the time we didn’t really know much about Brian Sabean. It was his first year as GM, and he had one aggressive (and, as I recall, shocking) trade under his belt already, the Matt Williams/Jeff Kent move. And here, in the middle of a pennant race, he had managed to add not the one useful part a fanbase hopes for but three? And by giving up only one prospect any of us knew anything about? For all that has defined Sabean over the years, the one consistent thing has been his ability to load up in July: Jose Mesa and Ellis Burks the next summer, Livan Hernandez in 1999, Jason Schmidt in 2001, Sidney Ponson, Randy Winn, Freddy Sanchez, Javier Lopez, Carlos Beltran, Marco Scutaro, Hunter Pence, Jake Peavy. In 1997, I never had any expectations for the trade deadline. Again, I’m not sure I even knew when it was. Brian Sabean, over the next two decades, made it his turf. —Sam Miller