Philadelphia Phillies: Ranking Their 5 Worst Trade-Deadline Deals Since 2000

As we enter into the month of July, baseball's trade rumor mill kicks into overdrive. By this point in the season, many teams have distinguished themselves as either buyers or sellers. Whether it be from poor production or an injury, many contending teams have been able to determine an area of need.

In recent years, few teams have been as successful as the Philadelphia Phillies in using the trade deadline to upgrade their squad. Fans have been spoiled with an annual Christmas in July with high-profile acquisitions such as Roy Oswalt and Cliff Lee.

However, there was a time when the Phillies were not a model franchise. There were many lean years where fans and the media alike picked apart the organization. They were seen as a team that made poor choices, had cheap owners and made questionable moves.

Given the success of the current era in Phillies baseball, sometimes it can be good to look back at those times in order to gain a better appreciation for what is currently happening in Citizens Bank Park.

This is a list of the worst deadline deals for those Philadelphia Phillies.

Good Bye, Curt Schilling

Few could have guessed that when young Curt Schilling was shifted from the bullpen to the starting rotation during the 1992 season it would kick-start a potential Hall of Fame career. Schilling would go on to be the Phillies' ace for the rest of the decade, including being the 1993 NLCS MVP.

However, entering a new decade, Schilling grew frustrated with Phillies management. Tired of watching his career stuck in neutral on a cellar dweller, he requested a trade. The Phils, frustrated with Schilling's stubborn personality, were glad to grant him his request.

On July 26th, 2000, the Arizona Diamondbacks acquired the ace right-hander for Omar Daal, Vincente Padilla, Nelson Figueroa and Travis Lee.

While with Arizona, Schilling went on to make three All-Star teams, win a World Series title and be named World Series Co-MVP. He then moved on to Boston where he helped anchor a Red Sox rotation that would win two titles in four years.

Meanwhile, in Philadelphia the only player from that deal to see any success was Vincente Padilla. Padilla lasted six years with the club, even managing to make one All-Star team. Figueroa and Daal were both shipped out of town within two years, while Travis Lee lasted just two-and-a-half mediocre seasons.

See Ya Later, Scott Rolen

Ever since Mike Schmidt retired in 1989, the Phillies had been looking for someone to fill his rather large shoes at third base. Scott Rolen was supposed to be that man.

He quickly endeared himself to the Philly faithful by winning Rookie of the Year in 1997. Over the course of his first six seasons in Philadelphia the Gold Glove defender would average 22 HR per year and a 125 OPS+.

Much like Schilling before him, Rolen was unhappy with Phillies management and questioned their desire to win. After turning down a hefty contract extension, things got contentious between the two.

At the end of the day, Rolen was dealt at the deadline in 2002 to the St. Louis Cardinals. The return on the trade was Bud Smith, Mike Timlin and Placido Polanco.

Bud Smith had thrown a no-hitter with the Cardinals, but arm problems prevented him from ever amounting to anything with the Phillies.

Mike Timlin pitched well for the remainder of the season and then left for Boston where he helped them win two World Series.

Placido Polanco ended up enjoying the most success with the Phils before being dealt at the 2005 deadline. More on that deal to come.

Dumping Bobby Abreu

This one may be one of the most controversial among Phils fans. There are two schools of thought when it comes to the Abreu deal.

One school says that it was addition by subtraction. These detractors often point out Abreu's apparent fear of the outfield wall and the relative ease with which he was willing to take a walk instead of being aggressive in clutch situations. 

Further evidence is the Phillies' season transforming after Abreu's departure on July 30th, 2006. With Abreu, the team had just a 48-54 record. After trading him they seemed to catch fire, going 37-23 down the stretch and falling a mere three games shy of the Wild Card.

On the other side of the coin are the fans who point out that the Phillies got nearly nine years of All-Star production from the right fielder. He was a 30/30 player and one of the toughest outs in baseball. The Phils made other moves to improve the team after the deal, including the acquisition of Jamie Moyer.

Furthermore, correlation does not imply causation. Just because the Phillies went 18-11 in each of the final two months does not mean that Abreu's departure was the reason. The Phils also went 17-11 in May of that season—with Abreu on the team. 

Instead, it was a June swoon that buried the team with a losing record; they had already started playing better prior to Abreu's departure in July. Abreu's presence on the team very well could have been the difference between making the Wild Card and staying home that October.

At any rate, Abreu being dealt as a pure salary dump meant the Phillies received virtually no assets to speak of in return. Jesus Sanchez toiled for years in the Phils farm system before moving to the mound and seeing some success. He is now in the Milwaukee Brewers organization. 

C.J. Henry had so little success that he was last seen playing college basketball for the Kansas Jayhawks.

Carlos Monasterios never made it to the Majors with the Phils, although the Dodgers did use a Rule Five draft choice on him. 

Matt Smith is the only player from the trade to play with the Phillies; he had a short-lived cameo before arm surgeries effectively ended his career.

Be Gone, Placido Polanco

As aforementioned, Placido Polanco was the one salvageable piece in the Scott Rolen deal. While not nearly the same hitter as Rolen, Polanco still swung a good stick and was able to provide strong defense at both second and third base.

With the Phillies having signed free agent David Bell to play third base, Polanco's time was limited to second base; however, the Phils had a big-time prospect by the name of Chase Utley who was ready to take the reins there.

Despite the fact that Polanco was a better player than Bell, the Phillies chose to platoon Utley and Polanco at second base. Since Bell had the big contract, it seemed as if Phils management was determined to play him every day, thus making two superior players split time.

When the 2005 deadline came around, it was Polanco who was shipped out of town for reliever Ugueth Urbina and utility man Ramon Martinez. Martinez spent 33 uneventful games with the Phils before moving on.

Urbina, however, was the big catch in the deal. The former All-Star closer was expected to shore up the eighth inning and make the Phils' bullpen a force to be reckoned with. While he played okay, the dominance envisioned never panned out, and the trade was considered to be a mild disappointment as the Phillies missed the playoffs by one game.

In the offseason, Urbina decided to go home to Venezuela where he would trade in the baseball diamond for a jail cell. After using a machete to attack a group of men who worked for him, he was charged with assault and attempted murder. Two years later he was sentenced to 14 years in prison. 

Meanwhile, Polanco developed into an All-Star second baseman and gave Detroit the best seasons of his career.

Re-Acquiring Mike Williams

Mike Williams was a Phillies farmhand who got his first real taste of the Major Leagues on the 1993 pennant team. After a few unsuccessful years with the Phils he moved on to greener pastures, eventually finding himself as an All-Star closer for the Pirates.

In recent years the Phils have found success with midseason acquisitions of struggling relievers with a history of success—the 2007 pickups of J.C. Romero and Scott Eyre are the best examples. In 2003, Mike Williams was an attempt at just the same.

The good news about the trade is that Williams' performance improved with the Phillies. The bad news is that when that improvement is going from a 6.27 ERA to a 5.96 ERA, it really makes no difference.

Williams would go on to have three saves, three holds and two blown saves. His poor results are part of what allowed the Phils to blow another playoff opportunity.

The one saving grace from this trade is that the man dealt away, Frank Brooks, never amounted to be much of anything on the major league level.