The Philadelphia Phillies' Seven Most Important Trades

After winning a second consecutive National League Pennant, but falling short of its goal to repeat as World Champions, the Philadelphia Phillies were very active over the winter.

Economics and Father Time served somewhat as a catalyst, but most of the activity was designed to position the team for success in 2010 and beyond.

On the heels of winning MLB.com's Executive of the Year Award, General Manager Rubén Amaro continued his bias towards action rather than take the safe route of standing pat.

Most of the moves we saw were simply the ebb and flow of free agents that overhauled the bench and bullpen as well as changed the face of the team's everyday third baseman.

The re-signing of former Phillie Placido Polanco to step in for Pedro Feliz is expected to provide an offensive upgrade with only a slight drop-off in the field. The other changes are not devoid of impact, but are expected to be of less consequence.

Except for those who were out of the country, or perhaps on the International Space Station, everyone knows the big news in Philadelphia (and throughout the entire baseball world) was the Phillies' swap of aces at the top of its rotation.

The tandem trades welcomed Roy Halladay to Philadelphia while bidding farewell to Cliff Lee on his one-way trip to Seattle.

Those dual deals involving two of baseball's biggest names sent considerable seismic waves through the team's fanbase, with many still feeling the aftershocks.

Fans are surely ecstatic to have arguably the best starting pitcher in all of baseball taking the ball every fifth day in a Phillies uniform.

However, a good portion of that excitement is tempered by knowing that Lee, last year's postseason hero, is now wearing Mariners attire.

In order to provide some backdrop to measure the magnitude of these two transactions, I have taken a look through the archives to find Phillies trades that may rival them in terms of importance.

Because the players involved in those December deals have yet to step across the white lines in a game that matters, it is too early to judge their impact.

So, although those blockbuster trades may prove to have the greatest impact—positively, negatively or cumulatively—it is premature to include them here.

It is interesting to note that throughout the Phillies team history, the club has more often come out on the short end when big name players have been involved, but that trend appears to be turning.

I present to you the (sometimes unlucky) seven most important trades in Philadelphia Phillies history.

No. 7: April 21, 1966

The Deal: The Phillies exchanged RHP Ferguson Jenkins, CF Adolpho Phillips, and 1B John Herrnstein to the Chicago Cubs for RHP Larry Jackson and RHP Bob Buhl.

Phillies GM John Quinn was looking to bolster the team's pitching staff with a couple of seasoned veterans. Unfortunately, both pitchers they obtained were a little too seasoned, as they were in the twilight of their careers.

Even more regrettable was the fact that the Phillies gave up their top young pitching talent in Ferguson Jenkins.

While the speedy Phillips anchored center, the tall right handed hurler went on to win 20 games the next six consecutive seasons for the Cubs on his way to registering 284 wins.

In 1971, Jenkins peaked with 24 wins and received the Cy Young Award. Of course, he was also later inducted into the Baseball Hall of Fame.

After coming close to winning the NL Pennant in 1964 and fielding formidable teams the next two seasons, the Phillies dropped like a rock until their resurgence began in 1974. It is doubtful that Jenkins would have improved those bad clubs enough to make a difference.

However, if he had been paired with Steve Carlton in the 70s, the Phillies near-misses throughout the rest of the decade may have been very different.

No. 6: July 26, 2000

The Deal: The Phillies dealt RHP Curt Schilling to the Arizona Diamondbacks for LHP Omar Daal, RHP Nelson Figueroa, 1B Travis Lee, RHP Vicente Padilla, and a bag of donuts.

This particular transaction proves that quantity does not make up for quality.

None of the players obtained amounted to much of anything, while Curt Schilling went on to lead a couple teams to World Championships.

After being dealt at the 2000 trading deadline, Schilling racked up a 45-13 record in Arizona the next two seasons. Interestingly, he came in second place each year in the Cy Young voting, finishing both times behind his own teammate Randy Johnson.

The duo dominated the 2001 postseason and led the Diamondbacks to a World Series title in just its fourth year of existence. This added insult to injury for Phillies fans, who had experienced just one championship in 119 years.

While Schilling would eventually join the Boston Red Sox for the bloody sock championship ride, the Phillies put together six straight near-miss seasons after his departure.

It does not take a great deal of imagination to surmise what those teams might have done if they hadn't given away one of the best pitchers in baseball.

No. 5: Oct. 7, 1969

The Deal: The Phillies sent 1B Dick Allen, INF Cookie Rojas, and RHP Jerry Johnson to the St. Louis Cardinals for CF Curt Flood, OF Byron Browne, LHP Joe Hoerner, and C Tim McCarver.

This deal represented GM John Quinn finally throwing in the towel by dealing the team's unhappy and controversial slugger, Dick Allen. The five-tool player is considered by many to be the greatest athlete and most exciting player to ever wear a Phillies uniform.

Just six seasons earlier, Allen was recognized with the National League Rookie of the Year Award for leading the Phillies on a yearlong flirtation with the pennant that famously ended with a crash landing over the last 10 games.

Allen went on to have many successful seasons on several teams, including an AL MVP performance in Chicago.

In a roundabout way, a case could be made that the Phillies eventually received close to commensurate value for their talented slugger, but the back story is what pushes this over the top in terms of importance.

Curt Flood was the key player in the deal coming from the Cardinals, but when he opted to sue major league baseball rather than report to Philadelphia, it changed baseball and professional sports forever.

The Flood case made it all the way to the Supreme Court, leading to the advent of free agency and arbitration.

The Phillies selected Willie Montanez, who contributed a few solid years before he was swapped for Gold Glove center fielder Garry Maddox, a stalwart on the 1980 World Series Championship club.

No. 4: Jan. 27, 1982

The Deal: The Phillies traded SS Larry Bowa and 2B Ryne Sandberg to the Chicago Cubs for SS Ivan DeJesus.

After contentious contract negotiations, the Phillies decided to swap five-time All-Star and Gold Glove shortstop Larry Bowa for Cubs shortstop Ivan DeJesus.

The slick-fielding Bowa was coming off a .283 season, while DeJesus checked in below the Mendoza line at .194. He was also one of the worst fielders in the league having committed 24 errors in just 106 games.

The deal begged to ask the question, "What were the Phillies thinking?" How could they trade their defensive anchor and spark plug for a light hitting, poor fielding shortstop?

Oh, yeah, and by the way, the Phillies threw in rookie Ryne Sandberg. Yes, the same Ryne Sandberg who was inducted into the Baseball Hall of Fame in 2005.

Over the next 15 seasons, the second baseman hit 282 home runs, drove in 1,061 runs, batted .285, and stole 344 bases. For his efforts, Sandberg collected nine Gold Glove, seven Silver Slugger, and one MVP award.

DeJesus graced the Phillies with three lackluster years of poor offense and shabby defense before moving on. Meanwhile, Philadelphia fans will forever wonder what their hometown team could have done with Sandberg in their lineup.

Enough said.

No. 3: July 29, 2009

The Deal: The Phillies acquired RHP Cliff Lee and OF Ben Francisco from the Cleveland Indians in exchange for four minor leaguers—RHP Carlos Carrasco, SS Jason Donald, C Lou Marson, and RHP Jason Knapp.

After a great deal of speculation about acquiring Roy Halladay, first-year General Manager Ruben Amaro reversed course and engineered a trade with the Cleveland Indians to acquire 2008 Cy Young winner Cliff Lee.

The brilliance of this trade was two-fold in that Amaro acquired such a talented pitcher without parting with any of the team's elite prospects, while at the same time foregoing the king's ransom being demanded by Toronto for Halladay.

All four players that the Phillies sent to the Indians are considered very solid, but none were ranked in the team's top five. Of course, it remains to be seen how they will develop and perform at the major league level.

Regardless, this trade is one of the organization's most important in team history because it most likely enabled them to reach a second consecutive World Series. Without Lee in 2009, it is very hard to envision the Phillies winning the NL Pennant.

For a team that had advanced to the Fall Classic just a half dozen times before, this is surely of historical importance.

No. 2: Nov. 7, 2007

The Deal: Phillies received RHP Brad Lidge and INF Eric Bruntlett from the Houston Astros for OF Michael Bourn, RHP Geoff Geary, and minor league 3B Mike Costanzo.

When GM Ed Wade landed in Houston after being let go by the Phillies, he promptly continued to place his imprint on his former club. In one of his first acts in his new home, Wade struck a deal with Pat Gillick, the man who replaced him in Philly.

While the move provided the Astros with what appears to be their starting center fielder for many years to come, it paid immediate dividends in Philadelphia of historic proportions.

Brad Lidge was arguably the single most important player on the Phillies 2008 World Series Championship team.

Without him the team most likely would not have taken that magical November trip down Broad Street, as Lidge put together one of the most remarkable performances in team history.

"Lights Out" Lidge took the ball in a save situation 41 times in the regular season, and then seven times more in the postseason, and converted on the opportunity each and every time.

In closer terms, he was an unprecedented perfect 48-for-48, giving the Phillies a death grip on games that they led heading into the last inning.

Even the most optimistic fans would concede that the Phillies second World Championship would not have been possible if not for Lidge's spectacular season.

Adding to the impact of the deal, Eric Bruntlett etched his place in team annals by sliding home with the clinching run in the series.

After a rough encore in 2009, it remains to be seen whether Lidge will be known as a "one hit wonder" in Philly, but there is little debate that those 2008 World Series rings have his fingerprints all over them.

No. 1: Feb. 25, 1972

The Deal: The Phillies acquired LHP Steve Carlton from the St. Louis Cardinals for RHP Rick Wise.

In a somewhat rare occurrence, the Phillies ended up as the big winner in this transaction.

The catalyst for the trade were ill feelings on both sides stemming from contract negotiations, so the two clubs swapped young pitchers with similar backgrounds.

Opinion at the time was that the deal was equal on both sides, but time would tell a very different story. Rick Wise continued to have a solid career, finishing with a 188-181 mark over 18 seasons.

As all Phillies fans know, Steve Carlton went on to have a Hall of Fame career, winning 329 games and becoming recognized as one of the greatest left handed pitchers of all-time.

In his first season in a Phillies uniform, Carlton assembled one of the best pitching performances ever by going 27-10 with a 1.97 ERA. What made it most astonishing is that he accounted for almost half of his team's 59 victories that season.

"Lefty" played 15 seasons in red pinstripes, racking up a fabulous 241-161 record with a paltry 3.09 ERA. Carlton also was recognized as the best hurler in his league by winning the Cy Young Award on four different occasions.

Carlton, along with Mike Schmidt, anchored the resurgence of the Phillies from the mid-seventies to the early eighties. Besides the current era of the team, this was the most prosperous period in team history.

The Final Word

Many trades have been made throughout the course of 127 years, but these seven trades stand out as having the greatest significance to the Phillies organization.

A quick tally suggests that three of them have worked out on their behalf, while the other four have contributed mightily to the success of their opponents.

The source of significance may vary, but each trade either left an indelible mark on the organization or left the void of "what could have been."

Two players proceeded to assemble Hall of Fame careers for their new team, while one did the same in red pinstripes.

One transaction sent another potential Hall of Famer out of Philly, but triggered an even larger chain of events that changed the face of the sport.

Three of the players exchanged donned their new duds and quickly played key roles in helping their new team to a title.

Although fate has not always been kind to the Phillies in making big trades, a closer look reveals a substantial change in recent years.

Over the past couple of years, the organization has endeavored to acquire high profile players in their prime, a practice that virtually never happened previously.

Shrewd moves by Gillick and Amaro have provided critical missing pieces that paid big dividends for the club.

Last year's National League Pennant was the team's seventh, and of course the ultimate payoff was the Phillies second World Championship in 2008.

Time will tell regarding this winter's big transactions, but there is little doubt that the 2010 "after" picture is better than the 2009 first half "before" picture. We will have to check the future brilliance of the rough diamonds exchanged and see how the coming baseball seasons unfold in Philly.

Also, a historical study suggests that Roy Halladay is likely the most accomplished, prime time player that the team has ever acquired via trade.

Another Red October culminating in a World Championship might turn this list from the "sometimes unlucky seven" to the "occasionally great eight."