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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

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sbnirish77
12/03
What part of .162/.237/.299/.536 (Stephen Drew) was better than .237/.300/.360/.659 (Brian Roberts)? The Yankees should have learned their lesson and the thought that they may bring Drew back to play SS should be grounds for dismissal.
mattymatty2000
12/03
The part where Drew had been a three win player the year before while Roberts hasn't played a full season since 2009.
Muboshgu
12/03
Boom
sbnirish77
12/03
Wrong. That's why the Red Sox signed him. Not the Yankees. The Yankees had the benefit of watching him go .176/.255/.328/.583 with the Red Sox at the beginning of the year after a disasterous signing. He actually was worse (.150/.219/.271/.490) with the Yankees making Roberts effort look like Rogers Hornsby.
mattymatty2000
12/04
I suppose reasonable minds can disagree about which player is better. That's fine. Either way, it's beside the point. The topic was surprising trades and the Red Sox making a trade with the Yankees after not making a trade with them for 17 years surprised me, and that's why I wrote about it.
Johnston
12/05
They were both awful. What does it matter which one was more of a dog?
Muboshgu
12/03
You understated the Marlins' return. Henderson Alvarez is an All-Star, and Nicolino and DeSclafani should both be mid-rotation arms. Plus, they got Marisnick, even if trading him and Colin Moran for Jarred Cosart doesn't work out.
thsaladboy
12/03
I found the Red Sox-Dodgers trade from a couple of years ago pretty shocking. The Sox unloading Adrian Gonzalez, Josh Beckett and Carl Crawford seemed to come out of nowhere, and who knew that such a large amount of contract could be unloaded at once? I remember my Dodger fan friends thinking they robbed the Sox blind, and me thinking it actually seemed pretty good for the Red Sox. I guess we were both right.
oldbopper
12/04
This is number one on a lot of lists here in New England. August 26, 2012 will always be a regional holiday in Red Sox Nation. This trade almost equals Heathcliff Slocumb for Derek Lowe and Jason Varitek for the best deal ever.
Robotey
12/04
There's no way this isn't on the list ahead of a Stephen Drew salary dump trade. This one was huge - paradigm shifting.
Johnston
12/05
Too right.
Guancous
12/03
"just goat-bites-your-daughter’s-nose-off-at-a-petting-zoo awful" (Riotous applause)
hotstatrat
12/04
The thing that was so disturbing about the Juan Gonzalez trade (as a Tigers fan) was that it was so antithetical to the Tigers' history. As I recall they were the last team to sign a highly sought after free agent - and even that one: Darrel Evans - wasn't on anyone's A list. The Tigers always seemed to be a rah-rah likeable bunch, who eschewed troublesome stars from other teams. This trade sliced off that point of pride.
DetroitDale
12/04
This trade was the ultimate indictment of Randy Smith but for a different reason, it wasn't because he gave up a boatload of young talent for a washed up malcontent superstar, but because since none of the "young talent" he traded panned out any better than the "young talent" he kept, his incompetents and evaluating talent and building a team was even worse than we already thought it was. Past articles on this site have identified Dave Dombrowski as the best GM in baseball, and that's validated not because of what he built in Detroit but what he built with the mess he inherited.
hotstatrat
12/04
Good/interesting points. But, while it is hard to criticize Dombrowski - after all he's done for us, etc. - the trading away of Fister for so little is still the head scratcher of the year. I guess, we have to be patient and see how Robbie Ray pans out. It is interesting how Detroit and Oakland geared up so for the play-offs - it seemed to backfire. Then within a week after Price and Lester trades, BP's own Russel Carleton shows us that starting pitching aces seemingly haven't helped teams at all in recent post seasons. I think that study stopped short of the Diamondbacks' Randy Johnson and Kurt Schiling show in 2001 (or Viola & Blyleven in '87 . . . or Koufax & Drysdale in '63 . . .)
Johnston
12/05
The Fister trade was so one-sided that it was offensive.
DetroitDale
12/05
Agreed, in fact I'm surprised the Fister deal wasn't on this list, as it appears a full out mistake by a man who rarely (but not never) makes mistakes. Even if Robbie Ray pans out, that's a couple years down the road at the expense of the current team that's otherwise in "win now" mode. At the time I thought they were clearing money for Joe Nathan, as that signing came days later, but if they couldn't afford $10M in Nathan (another mistake but only known with hindsight) in the offseason without dumping Fister why could they afford $7M and their two best pitching prospects for Soria in July (all so he could watch from the pen), to say nothing about Price?
hotstatrat
12/09
Yeah, all around it was Dombrowski's annus horriblus. Let's hope he's back on track this winter, but as a Torontonian I can tell you I had given up on Anthony Gose. He's still young, but he hasn't progessed at all in the last three years - when he should have been improving the most! I'm hoping they can do for him at least a little of what they seem to have done for JD Martinez, but that is pure dreamcasting. And, I don't see the other ex-Blue Jay Rajah Davis as an every day outfielder either.
HelicopterSunday
12/04
Ricky Nolasco was traded the following season.
dethwurm
12/04
And then the Tigers offered Juan Gonzalez 8yrs/$140 Million (in 2000 dollars)..... and he turned it down. #whoops
andrews
12/04
Please stop talking about Randy Smith, i had forgotten about him. Thank god Gonzalez did turn that contract down.
ironcityguys
12/04
If I remember the #1 Phillies/Cubs deal correctly (I was a young man just beginning to follow the sport then, but Ryne had played in my home town coming up, so the local paper gave hime a lot of coverage), the Cubs were holding out for an additional player in the Bowa/deJesus deal based on the age difference of the two shortstops and initially asked for Luis Aguayo. The Phillies balked at that deal and offered up Sandberg, an "untested 22-year old minor leaguer with good speed but a light bat" according to the Chicago Tribune, instead. Sandberg was blocked throughout the Phillies infield by guys like Schmidt and Trillo and wasn't thought of as a SS. There was even speculation that Sandberg would get a shot in CF if the Cubillies could find a way to move Steve Henderson. Dallas Green had just gone to the Cubs after 25+ years with the Phillies. Funny how things look in hindsight, but maybe the Phillies should have taken a closer look as Dallas played coy in negotiations.
DDriesen
12/04
I was driving my toddler daughters to a swim class early on a Friday evening in July 2004 when I nearly drove off Route 684 and crashed the car killing us all. Over the radio it was announced that the Mets gave away coveted top-prospect Scott Kazmir for perennial walk machine, Victor Zambrano. Called my other die-hard Mets fan friend Dave bewildered and searching for answers. Still have not gotten a good one a decade later. Runner-up Mets head scratcher (ala Phillies 2 for none deal) Mets clear up CF logjam of Mookie and Dykstra by getting rid of both and ending up with Juan Samuel. Good times...
JasonPennini
12/05
I enjoy Zambrano's 2003 stat line where he lead the league in BB, HBP, and Wild Pitches. The triple crown!
Robotey
12/08
I am relieved that I was neither driving nor had a daughter to endanger at the time of that trade. All I could do was spend years hoping that, at the very least, Kazmir wouldn't throw 7 no hitters.
bhalpern
12/04
I can't believe nobody has commented on Buhner for Ken Phelps.
DetroitDale
12/05
George Costanza's dad already did it as well as it could be done
Johnston
12/05
The Fister trade was terrible.
nwbaird
12/05
I remember watching a White Sox game on TV in August of '92 when Ken Harrelson broke away from play-by-play, saying they'd just received word of a "blockbuster" trade. "The Texas Rangers have traded Ruben Sierra, Bobby Witt and Jeff Russell to the Oakland A's for ... Jose Canseco." I remember a few seconds of silence before Tom Paciorek mustered a "Wow." Maybe my youth was a factor, but I can't think of another trade that made my jaw drop like that. I didn't conceive of players like Canseco getting traded, and that was a decent chunk of talent going the other way. It wasn't shockingly bad, just a shock.
Robotey
12/08
Imagine being a young Mets fan the night they announced they'd traded The Franchise --that was his original nickname--Tom Seaver for a handful of nothing. Took the real franchise a decade to recover.
JobuTheYounger
3/08
To anyone not knowing about the Arnold Johnson-Yankee connection, most of the deals between them had to shock. When Roger Maris was traded, the only player with any ability left was Norm Siebern.
JobuTheYounger
3/08
That should read "player acquired by Kansas City".