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January 10, 2011

What is the best and the worst trade in Orioles history?

Monday marked the 20th anniversary of the trade that sent three young players from the Orioles -- pitchers Curt Schilling and Pete Harnisch and outfielder Steve Finley -- to the Houston Astros for first baseman Glenn Davis.

At the time, I was in college and all my friends who were Orioles fans were psyched. The Orioles needed power, and Davis, who wasn’t yet 30, was one of the better sluggers in the National League.

But I hated the deal. And not because I knew Davis would be plagued by injuries and bad luck in his three years with the Orioles. I just didn’t like what the Orioles had to give up to acquire him.

I thought Finley would be good for a long time -- and he was -- but I wasn’t particularly wedded to the oddball Schilling, who had the best career of the three. It was Harnisch that was untouchable in my book.

Harnisch won 11 games and posted a 4.34 ERA as a 23-year-old in 1990. I thought it was dumb to give up a young, bulldog starter with plenty of upside and two other guys for Davis.

I thought Harnisch would one day be a star -- and though he never reached the heights I had imagined, he still had a 14-season career in which he won 111 games and posted a 3.89 ERA.

Schilling, of course, became one of the best big-game pitchers of the past 50 years, and Finley was just so solid for so long.

The trade, in my opinion anyway, was the worst in Orioles history. Its mirror image, for me, was the Dec. 9, 1965, deal that brought Frank Robinson to the Orioles and sent Milt Pappas, Jack Baldschun and Dick Simpson to the Cincinnati Reds.

I wasn’t born yet, but I have a friend who was a teenager at the time and said he hated the deal because he thought Robinson, a future Hall of Famer, was washed up and Pappas, who had gone 13-9 with a 2.60 ERA as a 26-year-old in 1965, was destined to be an ace.

So I guess we never really know about a trade until years later.

Well, in many cases, it’s years later. I want to know what you think are the best and the worst trades in Orioles modern-day history. My nominees are the Robinson deal and the Davis deal. But maybe I am forgetting something. Maybe you think the 2008 Erik Bedard deal to Seattle will one day be the best. Make your case.

Daily Think Special: What is the best trade and the worst trade in Orioles’ history?

Posted by Dan Connolly at 9:00 PM | | Comments (76)
Categories: Connolly's Corner Sports Bar


I don't think there's really anything to debate. The two you mentioned are the obvious 'winners.'

The Bedard trade looked great at the time, and considering what he's done since, it was still a very good deal. But Frank Robinson won a triple crown, MVP, and World Series in his first years as an O. He took the team to four WS in six years. There's no chance the Bedard trade (or any other) can possibly top that.

One date worse, December 4, 1988. Orioles trade Eddie Murray. Keeping Murrray, we would have kept Schilling, Finley, and Harnish and there would have been no Glenn Davis trade. Roland Hemond made both trades which sent this franchise down the wrong path.

Curt Blefray for Mike Cuellar was certinly one of the best, and trading Don Baylor, who went on to a few BIG years for a few months of a disinterested Reggie Jackson was a bad one. Earl Williams? Another waste. Whatever we gave for Pat Dobson was a steal and Enos Cabell for Lee May wasn't too bad either.

The Glenn Davis trade is the worst, no doubt. 2nd would have to be Eddie Murray to the Dodgers for Juan Bell, Brian Holten and Ken Howell. Ugh. The best was surely Frank Robinson. 2nd would probably be the trade that brought Dempsey, McGregor, Tippy and others.

Dan help me out on the parties involved in some of these...

Frank Robby for Pappas et al definitely is number 1...

10 player deal with the Yankees in '76(?) is up there...we got McGregor, Tippy, Dempsey, Dave Pagan...

getting a solid guy like Lee May for Enos Cabell in '75

Singleton and Mike Torrez in '75(I think--it's been a loooong time) for Coggins and McNally?

we got Reggie and Ken Holtzmann for Don Baylor, Paul Mitchell and Torrez....?

Roenicke and Stanhouse for I can't remember who in '77-'78?

Bad ones??? aforementioned deal for Glen Davis--I was sorriest to see Finley go--I wanted them to punt Brady Anderson instead--I'd make the same deal today---Anderson got better, but never was one of the smartest of outfielders...Finley was better over a longer period of time...

even though we didn't give up too much, the trade for Sosa was bad...

....but,,, the WORST trade of all--sending a Hall of Fame 1st baseman out of town(for Juan Bell, Brian Holton, and someone else who became Phil Bradley via another trade) because of an unthinkably stupid Cybex test on a sore hamstring insisted upon by a usually smart man (Bennett-Williams) who thought that since Eddie missed a few games(don't know the exact number but look it up--he was very reliable) that he was "dogging it" and the unfair painting of Murray by some irresponsible press at the time as "surly" because he didn't give them sound bites every time a mike was shoved into his face...I know Eddie "banned" a few of these guys, and there were bad feelings and blame enough to go around, but what a horrible day for the franchise...and for me personally...

The best that I recall was the Tippy, McGregor, Dempsey, etal. The worst, by far, hands down is the Glen Davis trade. The Frank Robinson trade sounded like a good one but that was before my time.

I don't remember too many 'big trades' that were good or bad. Glenn Davis deal was bad but that was more hindsight.

The one trade that tears at me wasn't really a 'bad' trade but it bothered me. It was when the O's traded BJ Surhoff to the Braves. BJ didn't want to leave and the haul the O's got never did anything good for the O's.

The best trade was getting Brady Anderson and Curt Schilling for Mike Boddicker. Or the 1995 mid-season trade for Bobby Bonilla. O's gave up 'prospects' that never really turned into anything other then solid back ups and got a proven middle of the order hitter for the stretch run. It did not work out that season. But Bonilla was a big part of the '96 season. And it showed the O's would actually go after a player instead of sitting back and letting the Yankees get everything to win... I miss those days.

The Frank Robinson trade was the best, and trading him away was, in my opinion, the second worst (after the Eddie Murray trade). We got Doyle Alexander, my least favorite Oriole of all time (until Keith Moreland in 1989) and, since the DH began the year after we traded Frank, he probably could still have performed for us in that role. Of course, it worked out pretty well for him, ultimately getting the Cleveland managerial job.

Nobody thinks the Big Money Williams deal where we sent Davey Johnson, Pat Dobson, Roric Harrison and Johnny Oates to Atlanta for a lazy overweight catcher who didn't want to catch wasn't 2nd worst behing the Glenn Davis deal.

I do.

The best was the Frank deal followed closely by the MASN deal. Still waiting on the payoff though.

Best trade was Pappas for Robby. The worst was a trade that never happened. We could have traded Ponson for some young first baseman named Adrian Gonzalez. Angelos wouldn't pick up what was left on Ponson's contract.

Any of Syd Thrift's 'deadline' deals can be ranked as some of the worse trades ever made. Mora was the only player we ever got from about a dozen guys who ever panned out. Thryft's drunken ineptness coupled with Angelos' meddling set the franchise back 10 years.

2000: Bordick to Mets for Mora, Mike Kinkade, Leslie Brea, Pat Gorman

2000: Harold Baines and Charles Johnson to White Sox for Miguel Felix, Juan Figueroa, Brook Fordyce, Jason Lakman

2000: Mike Timlin to Cardinals for Chris Richard and Mark Nussbeck

2000: Will Clark to Cardinals for Jose Leon

2000: Surhoff and Gabe Molina to Braves for Trenidad Hubbard, Fernando Lunar, Luis Rivera

2001: Mike Trombley to Dodgers for Geronimo Gil and Kris Foster

The Mickey Tettleton for Jeff Robinson trade was the DUMBEST in Orioles history.

At least with Glenn Davis, you EXPECTED the Orioles to get a power bat for a few years out of it. Most fans were pretty happy with the deal. I remember most joy and adulation from the fanbase when they completed the trade. Davis just imploded much earlier than pretty much anybody expected.

Jeff Robinson stunk before they got him. He was TERRIBLE. Tettleton had shown himself to be a rare and valuable commodity... a power-hitting, high-OBP, switch-hitting CATCHER. You don't trade a fairly rare "plus" talent (relative to his position) for a high-ERA, low-quality, reliably BAD starting pitcher.

Completely idiotic from the moment they agreed to the deal...

Flanagan and Beattie made some real gems:

2003: Traded Sidney Ponson to San Francisco Giants in exchange for Kurt Ainsworth, Damian Moss and Ryan Hannaman.

2003: Traded Jeff Conine to Florida Marlins in exchange for Denny Bautista and Don Levinski.

2004: Traded Denny Bautista to Kansas City Royals in exchange for Jason Grimsley.

2004: Traded Mike DeJean to New York Mets in exchange for Karim Garcia.

2005: Traded Jerry Hairston, Mike Fontenot and Dave Crouthers to Chicago Cubs in exchange for Sammy Sosa and cash.

2005: Traded Matt Riley to Texas Rangers in exchange for Ramon Nivar.

2005: Traded Larry Bigbie to Colorado Rockies in exchange for Eric Byrnes.

2006: Traded Jorge Julio and John Maine to New York Mets in exchange for Kris Benson.

2006: Traded Javy Lopez to Boston Red Sox in exchange for cash and a player to be named later; Baltimore Orioles received Adam Stern.

2006: Traded Jeff Conine to Philadelphia Phillies in exchange for a player to be named later; Baltimore Orioles received Angel Chavez.

2006: Traded Chris Britton to New York Yankees in exchange for Jaret Wright and cash.

I'll never, ever get over Finley/Schilling/Harnisch for Davis. Ever.

Side note - I think Bordick for Mora, et al was actually a decent deal, especially given that Bordick was a rental and was back at short the following spring.

Like Dave, I'm going to have to go with the 2000 fire-sale. Sure, a couple of those guys (Bordick and Surhoff) came right on back, but at the end of the day, you really just got Melvin Mora out of it.

Basically, the good deals we're recalling come from 1965-71 under Harry Dalton (with a nod to Lee MacPhail for sending Jackie Brandt to Phillies for Jack Baldschun and Norm Siebern to the Angels for Dick Simpson, then letting Dalton pull the trigger on the big one), and from 1975-87, under the guidance of Hank Peters.

The stinkers come from the likes of J. Frank Cashen 1971-75 (Robinson & Richert to the Dodgers for Royle, Doyle, Sergio and Bob, then Dobson/Johnson/Oates/Harrison to the Braves for Williams and Taylor Duncan), Roland Hemond 1987-95 and Syd Thrift 1999-2002.

You would be hard pressed to find any bad deals from Dalton and Peters, and even a couple of real steals - Dalton adding Frank, Cuellar, Dobson, even sending Luis Aparicio back to the White Sox for Bruce Howard brought us Spider Nelson and Don Buford, just the leadoff man for three straight AL champions.

Peters made the two deals with the Expos that brought Torrez & Singleton, then Roenicke-Stanhouse-Joe Kerrigan, the Lee May trade with Houston, the 10-player trade with the Yankees in '76. Plus all those little deals to get Floyd Rayford, Tito Landrum, Todd Cruz and the other role players who were so important on the two World Series teams.

Meantime, Cashen, Hemond and Thrift would have had trouble making change at a toll booth, let alone make a good deal.

Can't beat the Frank Robinson trade, but maybe the second best trade was the Bedard trade. In hindsight, we got rid of him right before his career collapsed due to a string of injuries. In return we got a blossoming goldglove allstar centerfielder, SP Tillman(or was it Butler?), and a reliever named Kam Mikolio, who combined with another reliever, got us our new awesome 3B Reynolds. Hopefully Bedard is healthy again this season and does well - I don't like to see others fail due to injury. Still, that trade has panned out really well for us so far.

Our second worst trade is probably the Reggie Jackson trade, because we didn't sign him to an extension and he skipped out to the Yanks. We gave up way too much for a rental player. The worst trade was of course the Glen Davis fiasco.

We coulda had AGaonzalez for Ponson? ARGHHHH lol

@ Gus,
I think Mike Flanagan and Jim Beattie were in over the heads. Their drafts were just as inefficient. Anyway, yeah Mickey T, trading Mickey Tettleton was a doozy. What made it even more odd, the Orioles only kept Jeff Robinson for one season. Speaking of switch hitting catchers, I am hoping Matt Wieters has a nice season here in Oriole Land. He has a pretty good team surrounding him in 2011 and it might even get better with a few more pick ups. Here's to Matt Wieters to having a break out season!

Friends, I'm not going to lie.

Eddie Murray, Glenn Davis, the 2000 fire sale, the Mike Flanagan era... they were all bad. All bad trades, bad signings, bad management. Just miserable.

So everyone's response is correct!

Great topic Dan, as it's hard to believe it's been 20 years since the trade!

Getting Frank Robinson changed the course of the franchise plus he managed one of my favorite Orioles team, the 1989 "Why Not?" squad that gave us an amazing ride till the final series in Toronto.

The deal that brought Brady Anderson and Schilling for Boddicker was an excellent trade for the O's. Brady had a long and productive career for the O's. He was a hell of a leadoff hitter and was exciting to watch on the bases.

Melvin Mora and others for Bordick was a great trade. Mora went from super sub to the 2nd best third baseman in O's history. No question that Melvin could be moody, but the guy turned himself into a great defensive player plus he loved Baltimore! He and his wife, did so many wonderful things for the community which I think has trickled down to BRob and Nick.

Jones for Bedard was another very good deal. Jones has a huge ceiling while Bedard is one more injury away from being out of the game. If Tillman turns out to be special, this would be the 2nd best trade behind the Robinson trade.

The lousy deals besides the Davis trade was the Jerry Hairston and Mike Fontenot deal for Sammy Sosa. I know BRob was given the job and rightfully so, but I always thought Jerry was athletic enough to play another position and it turned out that he is a jack of all trades. Sosa was driven out of Chicago and clearly on the downward spiral and not the guy that you rebuild with.

Jorge Julio and John Maine to Mets for Kris Benson was a bad deal, but I never classified it as horrible because Benson was the mentor that helped Bedard turn the corner. Bedard said it over and over again that he wouldn't of had success without the tutelage of Kris so I don't see the Jones deal going through without Benson helping out.

The Ponson deal was beyond sad because not one of the guys we got, did anything! This should have been one of those deals that restocks the farm system for years to come.

Not much to say about this ! You hit the nail on the head . No worst and no better .
Curt S.S. MD

I'm convinced that the only reason that Roland Hemond was infatuated with Jeff Robinson was because he almost threw a no-hitter against the Orioles the season before.

I happen to have a little age going for me, so I remember the worst early trade in modern Oriole baseball history—I’m assuming modern means since the O’s returned to the big leagues in 1954. It goes back to the O’s first season in the AL, 1954. The O’s traded outfielder Roy Sievers to the Washington Senators for outfielder Gil Coan before the season began.

Sievers’ stats for the Senators, 1954-1958
Year HRs RBI Ave.
1954 24 102 232
1955 29 95 253
1956 42 114 301
1957 39 108 295
1958 21 49 242
Sievers went on to have more productive years with the White Sox and Phillies before returning to Washington and ending his career in 1965

Coan’s stats.
Year HRs RBI Ave.
1954 2 20 279
1955 1 11 238
4 games for Giants in ’56 and then out of baseball

A momentous trade made after 1954 but not necessarily noted as good or bad is the 18-player trade with the Yankees that sent pitchers Turley and Larsen to the Yankees and brought Triandos, Woodling and Hal Smith to the O’s. Triandos hit 30 home runs in 1958. At the time it tied the American League record for most home runs ever hit by a catcher. He also made the all-star team a couple of times. Larsen went on to pitch the only perfect no-hit game in a world series for the Yankees, although I think Turley proved to be the better pitcher.

Peter Angelos for Eli Jacobs, downhill ever since.

Dont trade Murray dont needto tradefor Davis.Still never recovered. Could you imagine the rotation of Mussina,Schilling,Harnich,McDonald?I can and thus the reason why I am sick today.

Statistical records aside, I never liked Eddie, Eddie and bid him a fond farewell if we got nothing for him. "Mr. clean pants" was an enigma that didn't hustle and thought the media should pay for interviews. Davis trade the worst, followed by Turley-Larson trade to the Yankees. F Robby trade the best EVER!!

I am feeling kinda frisky today, so I feel the need to be positive! LOL

Since we are all talking about trades, maybe if the Rangers decide to sign Jim Thome the Twins will be looking for a left handed DH. That person could be Luke Scott. He's going to make around four (4) million in 2011. That's what they want to pay Thome, he might want more. So why not get something from the Twins again if we need something from them!

The Twins get a lefty DH for the price they want and we get something in return! Then we can go out and sign Vlad! Woo Hoo!

One of the wildest trades was with the Yanks in 1954. The O's sent Don (perfect game Larsen), Bullet Bob Turley and Billy Hunter to the Yanks for Gene Woodling, Willie Miranda, Gus Triandos and Hal Smith. There were also several other players involved. Larsen was 3-21 in 1954 but beat the Yanks for his 3 wins.

One of the wildest trades was with the Yanks in 1954. The O's sent Don (perfect game Larsen), Bullet Bob Turley and Billy Hunter to the Yanks for Gene Woodling, Willie Miranda, Gus Triandos and Hal Smith. There were also several other players involved. Larsen was 3-21 in 1954 but beat the Yanks for his 3 wins.

I'm just enjoying the beer, using it to celebrate the good memories and drown out the bad ones from all the comments. Dan listed the obvious answers, which were my answers too, and others have pointed out some of the runners up. If I think of something that hasn't been mentioned yet I'll come back and throw it into the mix.

McNally and Coggins to Montreal for Singleton and Torrez. McNally's arm was fried and he retired a short time later, and Coggins pretty much disappeared. Although Torrez was only with the O's for one year before he was traded to Oakland in the Reggie Jackson deal, he did win 20 games. Singleton was an excellent performer for a decade.

Wasn't Babe Ruth an Oriole once upon a time, used primarily as a pitcher?? Don't know if we traded him or not, but that was one player we should never have let get away. Of course, that was also pre-1954 Orioles, not the Baltimore team of today.

Everyone has mentioned the Davis trade and the trade to get Tippy and Mcgregor, but one of my all time favorites is Dave Mc Nally and Rich Coggins for Ken Singleton and Mike Torrez....

worst thing the orioles ever did, cant remember if it was a trade or free agent signing was alan Wiggins

I define the worst trade to be one that went against the conventional wisdom. The Glenn Davis trade doesn't fit that mold. Davis was a big slugger at the time (although injured for half of the previous season, and a low BA). All 3 players were considered expendable. Finley was 25, struggling, and being overshawdowed by Mike Deveraux, Joe Orsulak, and Brady Anderson (who outplayed Finley for the first few years after the deal). The O's already had what they beleived to be a glut of pitching prospect (the projected rotation of the future was Ben MacDonald, Mike Mussina, Arthur Rhoades, Jose Mesa, and Bob Milaki). Schilling was struggling, and didn't project as much more than a reliever, and Harnisch was not progressing as well as the others. So based on who the club had at the time, the move seemed like a good idea.
The real flaw of the O's in 1991 was not the trade, injuries happen, but the scouting. MacDonald never live up to the hype, Mesa and Rhodes went on to be relievers while Schilling became a starter.
On the other hand, the trade that gets little scorn and should was the Eddie Murray trade. Sure, Eddie wanted to go home to SoCal. But in 1988 the Dodgers had a reputation as a terrible trading partner, overvaluing their players, undervaluing other club's. Future HOFer Eddie Murray was traded for a couple of 3rd tier relievers, and a guy whose sole asset was that he was George Bell's brother who went on to be perhaps the worst player to ever wear an O's uniform (Juan Bell).

One of the few good trades made by Flannigan was the Sosa trade. We got a all star second basemen in the deal. Until that time they didn't know if Harriston or Roberts was going to be the future.



You're "feeling frisky" today? Maybe you ought to be reinforcing in your nest in your mother's basement instead of blogging on Orioles Insider...especially since your latest fantasy trade is "nuts"

Robinson for Papas is almost without a doubt one of the best trades this org has ever made. In fact Robinson for Papas by itself is almost a phrase worthy of Webster and is used on occasion by people when talking about one-sided deals. It’s one of the most memorable trades in not only baseball, but also professional sports.
As for trades that didn’t work out, I’d have to say Glen Davis, simply because he didn’t live up to the hype and we all knew that we were giving something good away to get him. Hard for us to imagine now, but sometimes you trade prospects for proven talent, especially when you’re trying to win a pennant right away, rather than in 5 years.

Great topic DC! A quick run down thru memory lane sure does sting doesn't it O's fans? with regards to trades that is, especially [Gus]'s post. Thanks Gus, I thought I had successfully erased the the Thrift Malaise from my memory banks. And to think, all that therapy money for naught! MLB Network just did a segment on worst trades of all-time in baseball and the Davis deal ranked 1st not just in Oriole-lore, but ALL of Baseball! hahaha-errrr-uuhhhh; OUCH, they're laughing at us! Yeh, but from 1950-1985 we had the winningest franchise in baseball! Yeh, remember when we used to drag that info out whne arguing against all the Yankee championships! Ok, back to the topic of best/worst O's trade all time, which certainly sheds new light on just how good a job Andy MacPhail is doing. He has correctly valued so far, not only our players, but the opposition too. How bout that gut check on the preposed deal for Barlett. only time is going to tell, but I think that was a great deal not done. Just as much as not trading away Britton or any other potential stud arms in the pipeline. Speaking of the pipleine, The Bedard deal is coming back in spades, heck a straight swap for Jones would have been a steal! It's the gift that keeps on giving, so all you AM haters, get to the back of the class, the dude is working extremely prudently to pull this franchise out of the Chesapeake muck.
Hands down, an not just because MLB network says so, Davis deal is the worst, and has been very eloquently defined by my bird bros above. I'll post the Bedard deal for modern day, Frank Robinson for yesteryear, as it brought a championship as a result as the best.

The trade that brought Tippy Martinez, Rick Dempsey, Rudy May, Scott McGregor and Dave Pagan to the Baltimore Orioles for Doyle Alexander, Jimmy Freeman, Elrod Hendricks, Ken Holtzman and Grant Jackson.

Barkeep listed the obvious best and worst trades in O's history. Josh is correct about how Finley, Schilling, and Harnisch were all viewed at the time of the trade. I seem to remember Davis had a great Opening Day game that year and then the nerve impingement in the neck soon followed. If only we knew then what we know now....

My votes for other bad trades go to:

Eddie Murray for the 3 loser Dodger prospects

Miguel Tejada for Luke Scott and 4 Astros prospects who haven't done anything for us

Mike Bordick, Will Clark, BJ Surhoff all traded for Melvin Mora and a bunch of nobodies.

Great O's Trades:

The trade that netted us Tippy, Dempsey, etc.

Erik Bedard for Jones, Sherrill, Tillman, Mickolio, and the other one. Jones has a gold glove and a all star game appearance under his belt; Sherill was an all star for 2 years and when traded, netted us Josh Bell (who the jury is still out on); Mickolio just brought us Mark Reynolds, and Tillman is almost major league ready.

I remember the Glenn Davis trade at the time it happened. I called a local sportstalk show (before the sportstalk stations existed) and bemoaned the trade as a loss of 3 possible all-stars for an injury plagued player ( at the time Davis had yet to complete a full season) Still one of the worst trades I've ever seen.
Frank Robinson, of course, is the best we've done.
The Bedard trade has yet to give us a great player but it got rid of one that can't seem to take the mound for any length of time.

I remember talking to my friend Charles Steinberg, an oriole front office emloyee just before the Davis trade and telling him I was worried about them trading Schilling, who I thought would be great. I agree witj both of your choices, Dan

The way that the Davis deal turned out, it is hard to imagine one worse. However, the Earl Williams deal certainly is a contender. For best, one can name several, imo. The F Robby deal was great, of course, but it was not exactly a steal Pappas was a fine pitcher. My other favorites were the acquisition of Lee May, the deal for Kenny Singleton, and snatching Jim Gentile from the DOdger system for a few bucks. A close runnerup would be sending an aged Fred Lynn to the Tigers for Chris Hoiles. In terms of a steal, however, it would be hard to beat the Bordick for Mora and Kinkade trade.

The Frank for Milt Pappas trade trade is mentioned in "Bull Durham" as the best in baseball history.
Beside the fact that Davey Johnson and Johnny Oates were both favorites of mine, I once saw Earl Williams warming up the starting pitcher while sitting on a milk crate. Johnson hit 44 dingers the following year while batting in front of Hank Aaron. Oates was never more than a journeyman as a player but of course he and Johnson both became decent managers. I guess Earl Williams bacame a milk man.

Frank Robinson hands down. He was with the Birds for six seasons and four of those we went to the World Series.
Stealing Cuellar was another one. Stealing Singleton was another brilliant one.
Yes, Glenn Davis was a flop but only because he got hurt. I saw him pinch-hit in Chicago and he lined a ball to left field about 400 feet. Only if he stayed healthy.

No contest for me, the 1979 trade:
5 Orioles (Alexander, Hendricks, Holtzman, Jackson and Minor Leaguer) for 5 New York Yankees (May, Martinez, Pagan, McGregor and Dempsey)
for two reasons
#1- it won the 1983 World Series when I was in high school (Dempsey MVP, McGregor shutout in clinching win, Tippy with 2 saves)
#2- it ripped off the Yankees

What more do you need?

I agree that the worst trade was for Davis. The O's gave up a lot for nothing.
The best trade was not for Robinson because the Reds got a really good pitcher, Milt Pappas, in exchange. The O's got the best of the deal, but the O's didn't make out like bandits. The best trade the O's made was to acquire Singleton in exchange for McNally who retired after the trade.

The Murray and Davis trades were the worst. Trading Tettleton for Jeff Robinson was bad, but no one has mentioned trading Phil Bradley to the White Sox for Ron Kittle.

Ed Miller--

"Mr.Clean Pants" is who got Ripken all those fat pitches to hit--for the most part, MCP had guys like Lowenstein, Roenicke, Dwyer (don't get me wrong--all good guys-all GOOD O's)batting behind him--for a while, we had a hellacious, HOF 1-2 punch in the heart of the order...too bad EBW got involved...

The Murray trade is on a different level. It is a top 5 worst trades by any team ever. It essentially ruined the franchise and they really haven't recovered since and probably never will. What would of happened in 1989 with the best clutch hitter in the game? I have a pretty good idea.

You nailed it Dan, Frank Robinson trade best, Glenn Davis trade worst. However, the jury is still out on the Eric Bedard trade. George Sherrill became our closer for the better part of 2 years and we got Josh Bell and Steve Johnson in return when we traded him at the deadline in 2009. Adam Jones has been our starting CF for 3 years, has won a gold glove, made the all start team and still may not have reached his full potential. Chris Tillman is still just 22 years old, turns 23 in April 2011 and people seem to have written him off. He could still make the starting staff and be just as good as Brian Matusz, Jake Arrieta, Brad Bergesen or Zach Britton. He has had great success at AAA, has struggled with a 5.63 ERA in 23 major league starts but Matusz, Bergesen and Arrieta have taken their lumps too and Britton (23 already) has just half a season at AAA. Kam Mickolio was part of the trade for Mark Reynolds who we control the rights to thru 2012 with an 11M option for 2013. So the Eric Bedard trade is already, in my opinion, the 2nd best trade in Os history. If you are keeping track Bedard has currently netted Adam Jones - our 3 yr starting, 2009 allstar, 2010 gold glove CF, Josh Bell - a switch hitting, power hitting 3B prospect at AAA who still has the potential to become a good major league ball player. Chris Tillman - 22 year old AAA righthanded starting pitcher who will be a major league starter soon. Indirectly - Mark Reynolds - 25 year old starting 3rd baseman for the next 2 years at least, who has averaged over 30 HRs over his last 3 major league seasons. His defense, initial below average, is now consider above average. Steve Johnson - son of former Os pitcher Dave Johnson and current AA prospect whom the Dodgers thought so highly of that they tried to get him back after the Sherrill trade thru the 2010 V5 draft, but they couldn't keep him on their major league roster so they had to offer him back. He struggled upon his return but still could help the Os in the near future and don't forget George Sherrill, while gone now, he was our closer for almost 2 years saving 51 games.

That’s a pretty good return for a pitcher that has made 30 starts going 11-7 over parts of 2 seasons and didn't make a start in 2010.

We still won't know how good the trade really was for several more years though. If a few of these players contribute to a World Series victory then I would say it surpasses the Frank Robinson trade.

How did a franchise that was the envy of most in baseball for it's great scouting and player development fall into such a pitiful state?

I'd say it was a successsion of a series of owners that have been determined to sqeeze every last buck out of the Baltimore fan base. One trade I 'd like to propose, the Angelos family for the Hoffenberger's any day of the week.

I've got to agree that McPhail has seemed to do a good job of trading to first unload overpaid, dead weight, that was stained in the steroids scandal, otherwise known as Tejada. And to sell high on the organization's best talent, Bedard.

Way to early to tell, but the Reynolds trade has great trade written all over it.

The Fred Lynn trade where Hoiles was a throw in is one not many think of. Freddy was near done and the O's plucked Hoiles out of the Angels low minors, case of great scouting.

The treatment of Eddie Murray and shipping him out of town for nothing was one of the O's all time low moments. Ownership and management weren't the only culprits in that one. A couple of Baltimore Sun employees lead the witch hunt for Eddie because of personal reasons, and plenty of fans were willing to jump on the bandwagon too.

It was a lynch mob mentality that chased a great player out of town when he was hurt. The guy had lead the team to two World Series and brought a championship to Baltimore and he had to listen to unspeakable crap on the radio, in the stands, and printed in our very own Baltimore Sun.

Not only was it a terrible trade, but terrible treatment toward a great Oriole, and a great guy in the clubhouse. A real low moment in O's history.

The Frank Robby deal to the Dodgers was a loser only because the O's didn't think Charlie Finley had the votes to get the DH passed the next year. The DH was designed for Frank and he was stuck in the National League for the first couple of years of it. With Frank Robby at DH, the O's could have notched a couple more trips to the Series.

Diamond Jim Gentile was a Dodger minor leagurer that the O's got in a minor league deal, went on to have one of the greatest years that no one talks about in 61'. Finished 2nd to Roger Maris in HR's, recently was awarded the RBI crown over Mickey Mantel, due to a correction, and I believe he was second in batting average. Was great to see him back at the Yard last summer.

Signing Vladimer Guerrero could go down as one of those alltime great moves. Wonder if the O's will have the guts to pull it off, or if the Angelos's are over their budget. going from last to wild card contention could be quite a feat. A couple more moves and it's possible.

On a completely different note, didn't Millar get traded for some equipment (bag of balls)when he was starting out in the independant league?

Cuellar for Blefray. A Cy Young Award and perennial 20 game winner (125 wins in 6 seasons) for a 3rd string catcher/reserve outfielder. Acquiring Frank Robinson will always be the best but he didn't come cheap. Cuellar was steal.

other notable trades

Good Trade:
Trading Fred Lynn for Chris Hoiles in 1988

Bad Trade:
1982 traded Doug Decinces for Dan Ford

Milt Pappas for Frank Robinson
Don Baylor and Mike Torrez for Reggie Jackson and Ken Holtzman.

Here's a bad trade from back in the "Orioles Magic" days - DeCinces and Jeff Schneider to the California Angels for Disco Dan Ford. This was supposed to make room for Cal to take over at 3rd - but, of course Cal went on to play SS - imagine if we had kept DeCinces at 3rd with young Cal at SS!

I'm testing memory here and didn't see this mentioned, so I'm probably mixing something in .. but didn't the O's trade Doug DiCinces for Dan Ford..? I recally DiCinces having some good years with the Halos and Ford being just a lazy and disinterested as Reggie was here for his brief stint.

The best trade was robinson -pappas. The worst was the Davis trade but special mention should be made of the three stiffs obtained for Ponson. The three players were so remarkably bad it was difficult to believe that would happen.

How about WORST trades not done (WORST because they should have happened).

Matt Riley, Jorge Julio and Larry Bigbie for AJ Burnett and Mike Lowell (and his contract).

Flanagan should have pulled the trigger...

BEST TRADE not done

Roberts and Penn for LaRoche

Getting rid of Ponson for anything, even a bag of flour, was a win. The guy was a fat waste of talent (evidenced by his lack of recent baseball employment).

December 4, 1974: Traded by the Montreal Expos with Mike Torrez to the Baltimore Orioles for Dave McNally, Rich Coggins, and Bill Kirkpatrick (minors).

This trade gave them a #3 hitter and a 20 game winner for McNally (who never pitched again) and Coggins (who the Expos picked versus Al Bumbry, as they were given the choice). Although Frank Robinson is my favorite player, this was the best trade.

They helped the O's to two series and alot of 90+ win years (and we got to keep Bumbry)

Nailed the top ones Dan.

I'm just praying that Hernandez and Mickolio for Reynolds doesn't end up on the bad list.

I really think Hernandez is going to be an absolute stud. Let's hope he's my Harnisch.

I also think, and again I hope I'm wrong, that Reynolds will continue his decline.

Worst trade ever was trading 48,000 Oriole fans for 35,000 Red Sox fans whenever they come to town

The best trade was sending Joe Carter to San Fran for Darin Blood! Yeah!!! . . . . .

I just want to trade Peter Angelos for a bag of Doritos. Anyone?

An alternative view:

Sure the F Robby trade was the best, but let's give Pappas his due. His career numbers are as good or better than some other pitchers in the HOF.

The Earl Williams tade wasn't the greatest, but the O's won two divisional titles with him. Trading Johnson to Atlanta opened up a spot for a pretty fair second baseman name o' Grich. Davey would have never hit 40 homers at old Memorial Stadium. He only hit that many in Atlanta because he was in a park known as "the Launching Pad." Earl's 20 homers meant more to us than Davey's 40 did for the Braves.

The Baylor-Jackson trade was a stinker, but then again free agency was in its infancy and no could foresee that Reggie and his ego would go to the Yankees for what was then an incredible amount of $$.

Likewise, no one could have predicted that a steady player like Glenn Davis would be such a wash-out here. That trade looked great at the time it was made.

Losing F Robby and Eddie were the biggest errors. And losing Eddie created the enviornment making the Davis trade necessary.

The trades bringing Cuellar, Buford, and Singleton here were excellent. But like they say, sometimes the best trades are the ones you don't make. There was talk after the '69 WS loss to the Mets about breaking up the O's core. Glad they didn't do that!

@ Ed Miller.
I guess you're the same guy who loved Billy Ripken because he got his uniform dirty. He could not hit way out of a paper bag and dove for ground balls most second baseman would field in front of them. Before Cal, Eddie had set the major league record for playing in 150 plus games for the most consecutive years. When a guy hits 30 Hrs and knocks in 100 Rbi's, in a time when that was a feat, who cares if his uniform is clean. He gets paid to play baseball not talk to the media. I call it the curse of Eddie Murray. We never should of traded him

Probably the last person to comment on this, but the Glenn Davis deal was NOT a bad deal. I am friends with Greg Riddoch, who managed the Padres for a few years in the early '90's. He worked in a sporting goods store in Greeley, Colorado in the off season, and I happened to be in there the day the Davis deal went down. Greg had managed against Davis for several years, and he knew I was an O's fan. When he saw me that day, he said the O's had just guaranteed themselves a couple of pennants because Davis was a beast who could carry a team for a month at a time. Freak injuries happen, but this trade, in itself, was a good one. If CC Sabbathia blew his elbow out two weeks into his multi-billion $$ deal with the Yankees, would you consider that a horrible deal? No, because the Yanks got a proven commodity. Davis was proven, too. He (and the O's) just happened to get the back break of a bizarre, career-ending injury. You really can't blame the front office for that. I mean, if anyone on this site can accurately predict when and to whom such injuries will occur, they are wasting their time on here. They should be selling their services for mega-billions to sports franchises all around the world. Best deal: you already know.

C'mon Dave... c'mon. Those are so obvious, how about this: next year, when all the sports journalists queue this question again, ask "Besides the Davis and Robinson deals, what *other* trades rank as worst, best in your opinion?" It's throwing out the extremes at either end and getting to some meaty conversation.

The #1 trade without a doubt is the Frank Robinson trade, I became an official Baltimore Orioles Fan that day. The Phillies blew the pennant in 1964 and I gave them their chance to redeem themselves in 1965 and they ended up in 6th place in the NL. Meanwhile my dad kept reminding me to keep an eye on those Orioles which I did. After that 1965 season the trade was made. I grew up in near Newport, Delaware and my family also bought a summer place in Fenwick Island in the spring of 1966 and lots of my neighbors there were from Baltimore. I have family upstate and downstate Delaware and we would go downstate in the summer at Fenwick Island and in the winter in Laurel and watch the Colts in Laurel and the Orioles in Fenwick Island during baseball season. In 1962 the Eagles traded away Sonny Jurgenson and Tommy McDonald to their rival teams Redskins & Cowboys and I would never forgive them. Meanwhile there was another QB in Baltimore named Unitas, he became my football hero, and Brooks & Frank were my baseball heros. Chuck Thompson excellent on the radio. The way it all ended up on October 9, 1966 I made my first visit to Baltimore with Dad and seen the Game 4 Orioles sweep over the Dodgers two weeks before my 13th Birthday. What a memory! My home is a Orioles shrine and Frank was MVP and won the Triple Crown. Worst trade? Glenn Davis. Earl Williams trade is up there too.

Although technically not a trade, the Orioles waived Jose Bautista in Jun 2004. Bautista went on to hit 50 home runs for the Blue Jays last year.

Any time the O's make a deal sending several young players away for one power hitter who is going to be "The Answer" I scream "Remember Glenn Davis!"

The demonstrably worst trade occurred in 1964, when they traded Wes Stock,
and a likely pennant, for Gino Cimoli. I don't know what Lee MacPhail was smoking that summer.

How about Aubrey Huff for Brett Jacobson? (kidding). Actually, that might turn out to be a good trade in the end, depending on how JJ Hardy does...

On a serious note, even as an 8-year-old, I was opposed to the Glenn Davis trade. I thought Harnisch pitched well in '89 (the year we missed the playoffs by a game), and I really liked Steve Finley, even though he had a ton of competition from Devereaux, Brady, Joe O, etc. I still think about that trade today and it kills me........

The 2000 fire sale is a different story because the O's weren't going anywhere with Clark, Surhoff, CJ, Baines, Bordick, etc. It was basically a salary dump. Should the O's have done better than Melvin Mora in terms of what they netted? Probably.....

Overall, trades haven't killed the O's, free agency has. Allowing Mussina to walk was idiotic. Signing Albert "Hide your kids if it's Halloween" Belle to a $65 million deal was insane. The O's also gave 3 yrs and $24 million to Javy Lopez. And letting Jimmy Key and David Wells go after the playoff years was also dumb. Ask Yankees fans, apparently Wells had a few more good years left in him...

Not breaking any news here, but the bottom line is that Peter Angelos, aka Satan, has hired some of the worst GM's in baseball history since Gillick left in '98.

I will say this, at least MacPhail kind of gets it with respect to free agency. He only gave Gonzalez a two-year deal and didn't extend Millwood (smart move). And at worst, if Reynolds tanks he could be off the books in 2 years - not terrible.

However, unless MLB allows more teams to qualify for the playoffs, I don't think the O's will win a title ever again in my lifetime.

I also wanted to say that I agree with people who cited the Ponson trade.

Here is a guy who was 14-6 with an ERA under 4 at the time of the trade. He was basically an ace, going to a team that was in a pennant race and considered him to be the missing piece of their puzzle.

I'll never understand how the O's settled for Kurt Ainsworth and Damian Moss in exchange for Ponson.

Again, Kurt Ainsworth and Damian Moss.

Likely the second worst trade the O's have made since I began following them.

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About the bloggers
A Baltimore native, Dan Connolly has been covering sports for 14 years, and baseball and the Orioles for 10 seasons, including the past six with The Sun. His first year covering baseball on a daily basis was Cal Ripken Jr.'s final season as a player. It's believed that is just a coincidence.

Steve Gould is an assistant sports editor for The Sun, overseeing Orioles coverage. The Columbia native joined The Sun as a sports copy editor in 2006 after graduating from the University of Maryland.

Peter Schmuck has been covering baseball for a lot longer than Steve Gould has been on this earth. He is now a general sports columnist, but has been a beat writer covering three major league teams (the Dodgers, Angels and Orioles) and also spent a decade as the Sun's national baseball writer. If you want more of his insight on the Orioles and other sports issues, check out his personal blog -- The Schmuck Stops Here.

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