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slant.gif (102 bytes) FTDOTC Special 10-Year Anniversary Edition


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December, 2008

Most Lopsided Trades in BDBL History

With Trading Season well underway, this month's FTDOTC "Special Anniversary Edition" will take a look at the most outrageous, most controversial, most one-sided trades of the league's first ten seasons.  And, make no mistake, there are a LOT of them to choose from.

What makes a "lopsided" trade?  Well, as I'm sure you're all tired of reading by now, I believe trades should be judged both by how they looked at the time of the trade and in retrospect.  The most truly awful trades -- the classics -- are the ones that were awful both at the time AND in retrospect.

However, there is also a second class of painful trades that looked reasonable at the time of the trade, but have turned out to be utter DISASTERS since then.  So, for the sake of completeness, I've also listed a set of trades that fall under this second category as well.

We begin with the trades that looked awful both at the time and in retrospect.

#1) 2002: Manchester traded Chipper Jones to Stamford for Ryan Dempster

This is the Cadillac of bad trades.  If bad trades were jewelry, this would be the Hope Diamond.  Every bad trade that has been made in this league since 2002 has been directly compared to this trade, and every other trade has paled in comparison.  Why is this trade still ranked as the #1 worst trade in league history every time we run a poll on the topic? Several reasons:

1. Jones had enormous market value at the time.  Over the next two seasons, he would hit .279/.379/.516 with 35 HR and 123.9 RC in 2002, and an amazing .372/.468/.539 with 147.7 RC in 2003.

2. At $8 million in salary in 2002, and with a contract that extended through the 2006 season, Jones was a bargain compared to his market value.

3. Dempster was in the final year of his contract.  With a salary only $5.5 million less than Jones, Dempster went 8-12 for the Irish Rebels in 2002, with a 4.28 ERA in 170+ innings.

What makes the trade even more of a classic is the fact that the lucky recipient of this stunning good fortune was the league's three-time defending champion, Paul Marazita.  As the legend states, this trade offer was actually initiated by Jim Doyle.  Out of 23 possible trading partners to bestow this gift upon, Doyle inexplicably chose the guy who'd won the league's first three championships.  All Marazita had to do was quickly accept without laughing too hard.

This trade helped Marazita extend his dynasty another couple of years, as he won his fourth trophy* in 2003, thanks in no small part to Jones' MVP-runner-up contribution.  As for Doyle, he ended up with nothing out of this trade except for massive amounts of ridicule.  His rationale for making the trade was that it saved him $5.5 million in 2002, and $39.5 million over the next four years.  But considering that Jones' salary was so far below market value, because Doyle could have gotten so much more in return for such a valuable commodity, and because Doyle had chosen Marazita as a trading partner, this trade may forever rank as the worst trade ever made in BDBL history.

#2) 2008: Manchester traded Scott Kazmir, Cole Hamels, Omar Vizquel and Wily Mo Pena to Marlboro for Yuniesky Betancourt, Gio Gonzalez, Phil Hughes, Barry Zito, Randy Wolf, Franklin Morales and Carlos Gomez.

If it seems like I'm picking on Jim, it's only because he deserves it.

Six years after making the worst trade in BDBL history, Doyle did it again.  This time, he traded two of the biggest assets in the league in exchange for several injured and/or unproven prospects.  In Doyle's defense, it may be a little too early to proclaim that this trade looks awful "in retrospect."  After all, it's only been a few months.

But already, we know that Marlboro will have two young ace pitchers in Kazmir (152+ IP, 123 H, 166 K, 3.49 ERA in MLB '08) and Hamels (227+ IP, 193 H, 196 K, 3.09 ERA), making just $4.7 million combined in 2009 -- roughly $32 million below market value.  So, before all those prospects Doyle acquired even step onto the field, they will be $32 million in the red on the tally sheet.  And that's just what they'll do in the coming season.  Kazmir is contracted through 2011, and Hamels' contract has yet to begin.

Is it possible for Hughes, Gonzalez, Morales and Gomez to outperform Kazmir and Hamels throughout the lifetimes of their contracts?  Anything is possible.  And Doyle certainly believes this will happen.  However, very few players have performed as well as Kazmir and Hamels at such cheap salaries, so the odds are certainly against it.

#3) 2007: Corona traded Ryan Braun and Tom Martin to Allentown for David Eckstein and Robb Quinlan.

As I compiled this list, I realized that the #1 cause of horrific trades is panic.  When a GM realizes that his team has what it takes to win a trophy, but is missing one key piece of the puzzle, he will often take drastic, foolish actions to acquire that missing piece.  Even if that missing piece is as relatively insignificant as a third outfielder to hit against lefties, or a setup man against righties, or a shortstop or catcher, contending teams will often panic just before the deadline.  And the results are never pretty.  I know this because I speak from firsthand experience.

In this trade, Corona GM Ed McGowan found himself with a glaring hole at shortstop, and after paying $21 million for Johan Santana, no money remaining to fill that hole.  So he did what so many others of us have done in a similar situation: he panicked.  As the 14th round of the draft approached, and with the Ridgebacks holding the first pick in that round, Ed pulled the trigger on a deal that sent his top prospect to Allentown in exchange for that pick.  And with that pick, he selected the diminutive, elfin-like David Eckstein.

Eckstein hit just .264/.309/.313 for Corona in 2007.  As for Braun, we all know the rest of the story.  He hit 34 homers in just 113 games to finish the 2007 MLB season, and won the NL Rookie of the Year award.  He then hit .327/.376/.595 for the Ridgebacks in 2008, and is now considered to be one of the biggest bargain assets in the BDBL.

#4) 2008: Manchester traded Matt Cain and Carlos Quentin to Kansas for Jonathan Papelbon and Eric Bruntlett.

Okay, this is the last time I pick on Doyle for awhile.  I promise.

Rule #1 in the GM Handbook is to never trade a quality starting pitcher for a relief pitcher -- especially when the starting pitcher is a 23-year-old ace with a $100,000 salary.  Rule #2 states: "and do not, under any circumstances, throw in Carlos Quentin just to make it even."

This trade was an unmitigated disaster for the Manchester franchise.  Instead of handing the ball to Matt Cain every fifth day, the Irish Rebels started pitchers like Steve Trachsel, Joel Pineiro and Barry Zito in his place.  It was a decision that may have cost Manchester their first shot at the playoffs.  But not only that, it cost the Irish Rebels a long-term, low-cost ace starting pitcher who will cost tens of millions to replace.

Then, just to add insult to injury, Quentin (.288/.394/.571, 36 HR) enjoyed a monster breakout year in MLB last season, and should be one of the biggest $100,000 bargains in the league next season.

#5) 2003: Cleveland traded Barry Bonds and Brandon Webb in a four-team trade with Allentown, Villanova and Great Lakes, in exchange for Cliff Floyd, Brad Wilkerson, Ryan Klesko, Robert Fick, Mark Bellhorn, Kaz Sasaki and Andrew Miller.

In 2003, the BDBL adopted an auction system to replace the draft for the top 50 free agents available each winter.  That year, Bonds was the #1 free agent in the auction.  The 38-year-old was coming off an MLB season in which he had hit .370/.582/.799 with 46 home runs and 198 walks.  At the time, the top salary ever paid to any player in the league was $10 million, and it was difficult to imagine how much a team would pay for a player like Bonds.  When the results of the first auction lot were announced, the league was shocked when Cleveland GM Mike Stein emerged as the winner with a mind-boggling bid of $16.5 million.

But Bonds only lasted four months on the Cleveland roster before Stein announced that he'd pulled off a blockbuster four-team, 18-player trade.  In that deal, Bonds ended up in Allentown, where he would carry the Ridgebacks to their second straight Eck League title.  Not only did Stein sacrifice Bonds, however, but also Webb, who would soon become a perennial Cy Young candidate at a dirt-cheap salary.

In exchange, what did Stein get out of this deal?  The Rocks finished 19 games out of first place in the division in 2003, and six games behind in the wild card race.  Floyd batted 344 times in 2004 at a salary of $7 million before Stein paid a $4 million penalty to release him.  Wilkerson had a couple of decent seasons for Cleveland in '04 (.240/.357/.384, 82.4 RC) and '05 (.232/.365/.407, 94.7 RC) before Stein paid a $1 million penalty to release him as well.  Klesko cost Cleveland $3 million to release that winter.  Fick and Bellhorn were free agents at the end of '03.  Sasaki pitched just one more season in the BDBL (37 IP, 36 H, 20 BB, 26 K, 3.41 ERA in 2004.)  And Miller was eventually released.

In total, Cleveland paid $8 million in penalties, plus sacrificed five years of below-market dominance from Brandon Webb, all in exchange for the greatest hitter in league history.

#6) 1999: New Milford traded Randy Johnson and their #2 and #6 draft picks to Stamford for Jose Rosado, Daryle Ward and Stamford's #2 and #6 draft picks.

One of the first trades ever made in the BDBL, some credit this trade with directly leading to three straight championships by the Stamford Zoots.  It is difficult to argue that the Zoots could have accomplished such a feat without Johnson.

At the time of the trade, the 35-year-old Johnson (New Milford's #1 pick in the inaugural draft) was a bitter disappointment for the Blazers, as he owned a 2-10 record with a 6.81 ERA in a dozen games.  With the Blazers going nowhere in the standings, New Milford GM Billy Romaniello reconnected with his favorite old trading partner from the CBL, Paul Marazita.  In exchange for Johnson, Romaniello received a couple of young and promising players in 24-year-old pitcher Rosado and 25-year-old Ward.  Unfortunately for Romaniello,  Rosado would never fulfill his promise, and he ended his three-year BDBL career with a 5.47 ERA and an 18-34 record.  And Ward would prove to be nothing more than a career pinch hitter.  In his ten-year BDBL career, he has managed 150 at-bats in a season just once (.246/.304/.354 in 342 AB's in 2003.)

Of course, Johnson went on to win five BDBL Cy Youngs and five World Series rings over the next six seasons.  And if that were the end of this story, that would be enough to warrant a place among the top 10-15 worst trades of all time.  But, as with many trades appearing on this list, it was the "throw-ins" that made this a truly classic trade.

With the Blazers ensured of finishing with the worst record in the league in 1999, this meant they would own the #1 pick in each and every round of the 2000 draft.  And with such a thin draft pool in 2000, it was argued that New Milford's picks were the only worthwhile picks of the entire draft.  And out of all their picks, their #2 and #6 picks were the most valuable, as those were the first picks of the $5 million and $3 million salary tiers.

Evidently, it wasn't enough for Marazita to simply end up with the greatest pitcher in league history in this trade, so he somehow convinced Romaniello to throw in his #2 and #6 picks as well.  He soon discovered that those picks had far more trade value than they were worth, and flipped them.  For that #2 pick, he received hot young prospect Darin Erstad and a 16th-round pick.  He then flipped Erstad to the Akron Ryche for Eric Davis (.358/.410/.618 in 123 ABs for Stamford) and Ricky Bottalico.  And for that #6 pick, he received Ramiro Mendoza and Luis Alicea.  Johnson, Davis, Mendoza and Alicea not only played key roles for the Zoots in the 1999 playoffs, but in 2000 as well.

#7) 2007: Manchester traded Yovani Gallardo, Adam Loewen and Jarred Saltalamacchia to Chicago for Ivan Rodriguez and Kurt Suzuki.

Yep, back to Doyle.

As I stated earlier, panic has often been the #1 cause of bad trades in the BDBL.  In this case, Doyle found himself in a tough situation heading into Opening Day.  He went into the auction with a team that was favored to win the division.  And with nearly $36 million to spend and only a few holes remaining in the starting lineup, the Irish Rebels were in an enviable position.

But Doyle went nuts in the auction, spending $20 million on his #3 starter, C.C. Sabathia, and another $14.5 million on roster fillers Rich Aurilia, Dan Wheeler and Ty Wigginton.  As a result, he found himself with just $1.3 million remaining and 13 holes left to fill.  The most important of those holes was behind the plate, where part-timer Jose Molina was the team's only option.

At the same time, John Gill of Chicago found himself with two full-time catchers after signing Ivan Rodriguez to a $5.5 million deal on the final day of the auction.  As he didn't need Rodriguez, and most likely bid on him for the sole purpose of driving up his salary, Gill immediately placed Rodriguez on the Selling forum.  Doyle responded, and the rest is BDBL legend.

Simply trading any one of the three top young prospects Doyle sacrificed in this trade would have been enough to warrant consideration for this list.  But the fact that all three players were traded for a stopgap solution makes this trade a classic.

#8) 2003: New Milford traded Kevin Millwood, Randy Winn and Wil Cordero to Stamford for Horacio Ramirez and Zach Day.

Once again, a Romaniello/Marazita trade earns a spot in the top ten.  Here, the Blazers found themselves selling off every marketable player on their roster in yet another effort to rebuild, and once again Marazita played the role of the circling vulture.

At the time, Millwood was among the top pitchers in baseball, and was by far the hottest commodity on the trading market that summer.  Romaniello collected numerous offers for Millwood (including my offer of B.J. Upton), and in the end, somehow determined that Marazita's was the best.

In the five seasons since this trade, Ramirez has racked up an ERA of 5.50, and has gone 26-34 in 100 games.  Day lasted just two seasons in the BDBL following this trade, and ended his BDBL career with a 19-16 record and a 4.40 ERA in 309+ innings.

But, once again, it was the "throw-ins" that made this trade a classic.  Simply acquiring Millwood for a pair of sub-mediocre pitchers would have been a coup for Marazita.  But adding Winn (.298/.360/.461 in MLB '02) and Cordero (.309/.373/.459 for Stamford in 2004) just seemed like unnecessary piling-on.

#9) 2002: Arizona traded Curt Schilling and Eric Gagne to Allentown for Russ Ortiz, Erubiel Durazo, Ron Belliard and Jimmy Anderson.

It's difficult to imagine, but at one time in this league's history, Tom DiStefano had yet to win a single BDBL trophy.  But in just his second full season in the BDBL, DiStefano's Ridgebacks were picked to not only win their division, but were favored to win the BDBL championship as well.  Then, on March 6th of that year, he connected with Arizona Heat owner Mike Leuck to pull off one of the biggest heists in league history.  And it was that trade that established DiStefano's reputation as a Sith master and earned him the nickname, "The Emperor."

At the time, Schilling was among the best pitchers in baseball.  In terms of VORP, only Schilling's new Allentown teammate Randy Johnson ranked higher.  On the season, Schilling went 20-7 with a 4.02 ERA, 292 strikeouts and only 43 walks in 262+ innings overall.  For the Ridgebacks, he went 17-4 with a 3.64 ERA in 215 innings.  Signed through the 2003 season, Schilling was a bargain at $10 million in salary.

The package of players received by Arizona in this deal (whose salaries totaled $3.2 million more than Schilling) was dubious at best.  Durazo played just one more year under contract, and amassed just 194 at-bats that season.  Belliard suffered through a horrendous MLB season in 2002, and was released with a $2 million penalty that winter.  And Anderson pitched just 26 innings in 2003 at a salary of $2.1 million -- his final season in the BDBL.

The one and only saving grace of this trade from Arizona's standpoint was Ortiz, who -- despite issuing a mind-boggling number of walks -- pitched two more seasons under contract at $5.5 million and $7 million, and was traded that winter for Gary Sheffield.

However, any value held by Ortiz was negated by the fact that Leuck inexplicably threw in young prospect Eric Gagne, who became the top closer in the BDBL in 2003.  Again, it was the "throw-in" that transformed this trade from "lopsided" to "legendary."

#10) 2002: Litchfield traded Barry Bonds to Allentown for Bartolo Colon, Sean Casey and Jerome Williams.

It's almost impossible to put a price tag on a player like Bonds, circa 2002.  In MLB '01, Bonds had broken the MLB record for home runs, hitting 73.  He hit an astounding .328/.515/.863, walked 177 times and created more than 200 runs.  Bonds alone would have carried a team into contention.  And at only $10 million in salary, and in the final year of his contract, it is likely that no player in BDBL history has ever been more valuable.

Considering all of that, it is utterly remarkable that the Litchfield Lightning received so little in return for such a player.  Colon was a decent pitcher, and a real workhorse.  Over the next three seasons, he would pitch 731+ innings, compiling an ERA of 4.36.  But with a contract that would pay him $37.5 million over the next four years, he was hardly a bargain.

Casey was also a fine hitter, hitting .316/.383/.438 with 107 runs created in 2002.  But his performance would soon take a dramatic downturn.  And he, too, was locked in to a very expensive ($26 million over four years) contract.

Incredibly, Colon and Casey combined earned $3 million more than Bonds in 2002.  So, in addition to downgrading his team, Litchfield GM Phil Geisel was also losing a substantial chunk of salary.  This, however, was thought to be offset by the inclusion of Williams, who was considered to be among the brightest young pitchers in the minor leagues.  Unfortunately for Geisel, Williams would never quite fulfill his vast potential.


And now for the sub-category.  These are the trades that may have looked reasonable at the time of the trade, but due to the development of the prospect(s) involved, they now look horrendously painful in retrospect.

#1) 2001: Litchfield traded Lance Berkman and Adam Piatt to Salem for Darren Dreifort.

This trade was the culmination of two years of non-stop pestering on my part.  Eventually, Geisel was desperate enough for a quality starter that he finally gave in.  Ten years later, Berkman has racked up 934.9 runs created, and owns a career line of .290/.406/.512.  I believe he's the only player ever to play more than three seasons for the Cowtippers.

#2) 2000: Plattsburgh traded Mark Teixeira to Salem for Wes Anderson.

With this trade, I pestered original Plattsburgh owner Tim Zigmund again and again about the availability of Teixeira.  At the time, T-Rex was just a freshman in college.  I had planned to draft him in the 2000 farm draft, but Zigmund beat me to the punch by picking him up in the final chapter of the 1999 season (back when we allowed farm free agents to be selected in every chapter.)  When Zigmund resigned, I pinged the new owners, and sure enough, they weren't nearly as in love with Teixeira.  I was a big fan of Anderson, but it was a very easy trade to make.

#3) 2002: Salem traded Grady Sizemore, Michael Aubrey and Greg Swindell to Litchfield for Steve Karsay.

I know...another Salem trade.  But this time, I came out on the short end of the bargain.  And this time, Geisel was the beneficiary, which somewhat makes up for the Berkman trade.  The background on this trade is pretty typical.  I needed a middle reliever, and Geisel was rebuilding.  I offered a few prospects I thought were unneeded excess, and the rest is history.  At the time of the trade, Sizemore was a 19-year-old A-ball outfielder with 6 career home runs in over 1,000 at-bats.  Who knew?

#4) 2003: Wapakoneta traded Omar Daal, Andy Fox and Joe Mauer to Stamford for Trot Nixon and Juan Cruz.

This one is a BDBL classic, and yet another one with a personal facet for me.  I had practically begged Bobby to trade Mauer to me for months before this trade, and each time my pleas were met with resistance.  Then, I went on vacation.  And when I returned, I received a giddy e-mail informing me that not only had Mauer been traded, but to my arch-enemy, Marazita.

Bobby has defended this trade recently by pointing out that he saved $5 million in this trade, and that Nixon (.232/.331/.411, 61.7 RC) wasn't completely useless in '03.  But let's be real for a minute.  This is Joe Mauer we're talking about.  End of debate.

#5) 2002: Cleveland traded Roy Halladay, Joel Piniero, Josh Paul and Brian Hunter to Southern Cal for Jon Lieber, Matt Lawton, Trevor Hoffman and J.T. Snow.

Mike Stein traded a lot of good, inexpensive players through the first eight years of this league's history, all in an effort to make the post-season.  This was just one of those trades.  Just one year after this trade, Halladay (20-7, 2.63 ERA in 263 IP) became perhaps the best pitcher in the league, at only $100,000 in salary.  And two years later, Piniero (17-11, 3.08 ERA in 228+ IP in BDBL '04) joined him.  Meanwhile, Lieber, Lawton, Hoffman and Snow didn't get Cleveland any closer to the playoffs.

#6) 2001: South Carolina traded their #1 farm pick to Salem for Matt LeCroy.

Matt LeCroy (who is now managing a team in Single-A) has been involved in a lot of bad trades in the BDBL, but this is probably the worst of the lot.  The reason is that South Carolina held the #2 overall pick in that 2001 farm draft -- a draft that included the likes of Albert Pujols, Mark Prior, Roy Oswalt, Jake Peavy, John Lackey, Chase Utley, Carlos Zambrano, Justin Morneau, Hank Blalock and Ichiro Suzuki, to name just a few.  Unfortunately, I later traded that pick, and Sharky ended up with Ichiro.

#7) 2003: Salem traded Scott Shields and Justin Verlander to Akron for Guillermo Mota and Kris Honel.

If it seems like Salem has been involved in a lot of awful trades involving prospects, it's only because it's true.  This was one of those deals where teams exchange players who are underperforming, hoping a change of scenery will help.  In this case, both Shields and Mota were performing well below what DJ and I expected.  Why we insisted on throwing in Verlander and Honel, I'll never know.  But at the time, I figured I'd rather take my chances on a former first-rounder who'd already proven himself in the minor leagues than a pitcher who was still a junior in college.  You win some, you lose some.

#8) 2004: Marlboro traded Ryan Howard and Scott Olsen to Nashville for Aquilino Lopez and Dan Plesac.

Aquilino Lopez pitched all of 9.1 innings for Marlboro that year, while Plesac pitched a whopping 12.2 innings for the Hammerheads.  That's one hell of a price to pay for 22 innings.

#9) 2002: Villanova traded Carl Crawford and Jeremy Burnitz to Kentucky for Moises Alou.

Alou hit a very nice .320/.390/.473 for the Mustangs following this Chapter Five trade.  Unfortunately for 'Nova, Alou couldn't carry the team into the playoffs.  The Mustangs went just 26-28 over the final two chapters and finished a dozen games out of the wild card race.  As for Crawford and Burnitz, I think they turned out a little better.

#10) 2002: Bear Country traded Hideki Matsui and Willie Harris to Gillette for John Burkett.

Matt Clemm made BDBL history when he selected Matsui as the first-ever NPL player on a BDBL roster.  But when he found himself in the heat of a pennant race in 2002, he thought nothing of sacrificing a player who'd yet to play a single game in the US.  In Matsui's five-year BDBL career so far, he's hit .277/.365/.457, with 445.6 runs created -- at a combined salary of just $9.6 million.


Why stop at ten?  Here's ten more:

#11) 2002: Marlboro traded Carlos Zambrano to Chicago for Mike Trombley.

And thus began the never-ending game of "Hot Potato" between Ken Kaminski and John Gill.  Over the next six years, Zambrano would switch between the Hammerheads and Black Sox SIX times -- not counting this trade!  As for Trombley?  He posted a 6.35 ERA in 41+ innings for Marlboro in 2002, and then never pitched in the BDBL again.

#12) 2000: Salem traded Alfonso Soriano and Michael Tejera to Minneapolis for Armando Rios and Minneapolis' #2 and #4 farm picks.

Ah, yes, another foolish Salem trade.  Here, I was desperate for a left-handed pinch hitter for some reason.  And I was convinced that I needed to trade Soriano immediately, because his trade value would never be higher.  I remember offering him to every team in the league, but no one wanted him.  Finally, Minneapolis GM Eric Zigmund took the bait, and then immediately flipped Soriano to his brother, Tim.  I never forgave him for that.

#13) 2003: Wapakoneta traded Prince Fielder, Mark Grudzielanek and Mike Matheny in a three-team trade with Southern Cal and Chicago, in exchange for Eli Marrero, Luis Castillo and Brent Abernathy.

Marrero hit .277/.315/.555 for the Hippos, in just 119 at-bats, in his final year under contract.  Castillo hit a singles-fueled .324/.391/.415 -- also in his final year under contract.  And Abernathy logged just 53 at-bats, hitting .264/.328/.377 in his final year under contract.  Three sub-par, part-time slap-hitting free-agents-to-be for Prince Fielder?  AND he threw in Grudzy and Matheny?  What on earth was Bobby thinking?

#14) 2005: Wapakoneta traded John Lackey and Felix Diaz to Bear Country for John Thomson.

Man, Bobby has traded away a LOT of good young players over the years: Lackey, Fielder, Mauer, Bay, Pedroia, Papelbon, and now Chamberlain.  Can you imagine the team he'd have if he'd kept them all?  How can anyone trade away so many good, young players?  It reminds me of a fable I once heard about a young man with a pot on his head...

#15) 2008: Southern Cal traded Ervin Santana and Joey Devine to Atlanta for Jesse Litsch.

We don't yet know the full extent of how this trade will look in terms of BDBL performance, but it's safe to say that Gene made out pretty well in this deal.

#16) 2006: Corona traded Jay Bruce to Salem for Ray Durham and Max Scherzer.

Durham hit just .264/.347/.349 for Corona before he was traded.  And although Scherzer later netted Edgar Renteria in trade, I think Ed wouldn't mind having this one back.  Of course, as someone who has also traded Bruce, I can relate.

#17) 2006: Bear Country traded Kevin Youkilis to Los Altos for Russ Springer.

Springer pitched a little more than nine innings for Bear Country, in the final year of his contract.  They weren't even good innings, unfortunately, as he allowed eight runs.  But he was later traded to Salem along with Mike Piazza in a deal for Edinson Volquez, so it all worked out. 

#18) 2007: Bear Country traded Edinson Volquez to San Antonio for Kevin Mench and Travis Ishikawa.

Err...okay, I take that back.  It didn't work out too well for Bear Country.

#19) 2006: Bear Country traded Dustin Pedroia and Gary Bennett to Chicago for A.J. Pierzynski.

Sorry to pick on you so many times in a row, Matt.  But trading the reigning AL MVP for A.J. Pierzynski deserves a spot on this list.

#20) 2007: Cleveland traded Dustin McGowan to Salem for Santiago Casilla.

This may be the best trade I've ever made.  At the time of the trade, McGowan was sporting an ERA over 5.00.  But I thought it was worth taking a flier on him, so I pulled the trigger, despite the fact that Casilla was having a very good year to that point.  The very next game McGowan pitched in MLB, he took a no-hitter into the ninth.  He proceeded to post a 3.67 ERA over the second half of the season, and became one of my best pitchers this past year.  If only he didn't blow out his shoulder, this story would've had a happy ending.