Philadelphia Phillies: 25 Most Controversial Player Moves of All Time

Nine times out of ten, player transactions are a game of chicken.

In a trade, you have two, professional, MLB organizations desperately trying to get the best of each other, because let's be honest: As many times as we've heard a general manager proclaim that the deal "made sense for both sides," we all know that each team is trying to get the deal's best possible player for the least possible price.

In free agency, agents will do everything in their power to create leverage for their client. They'll build up another team's interest. When negotiations begin, they'll shoot for the stars while the organization does just the opposite until one side caves in.

The same could be said for lesser transactions like the draft, where potential draftees hold things like a commitment to a college against a team, or the waiver wire, will teams will try as hard as possible to look uninterested in a player.

The bottom line is this: This game of chicken hatches controversial player moves.

Sometimes, teams have to take risks on a deal. Sometimes they have to overpay for a free agent, send that extra top prospect to a rebuilding team, go over slot for a player in the draft, so on and so forth. It's not always rainbows and butterflies in negotiations, and teams will fight tooth and nail to come out on top.

Teams won't get anywhere in this game—this business—without taking a few chances. A lot of times, that leads to a huge controversy over whether or not they made the right decision, and this slide show will examine those controversial transactions in the history of the Philadelphia Phillies.

Before we begin, however, it is important to note that these transactions will be evaluated at the time of the transaction's execution. Hindsight is 20/20. A deal that seemed controversial at the time of its execution may not seem that way after a player has years of success.

So please note that each and every deal on this list will be evaluated as if it just happened. After all, that's what makes it controversial.

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25. Montanez Dealt to San Francisco

The Deal: Phillies trade Willie Montanez to the San Francisco Giants in exchange for Garry Maddox.

The Phillies had always wanted a good defensive player to patrol the spacious confines of center field, and Garry Maddox was certainly capable of that.

The real controversy in this deal was the player heading the other way: Willie Montanez.

The Phillies had acquired Montanez as part of the deal that sent Dick Allen to the St. Louis Cardinals, and many people believed that he had yet to live up to his full potential, while Maddox's bat had its question marks over the long haul.

Sure enough, this was a deal that worked out well for the Phillies, as Maddox patrolled center field for a World Series club.

24. Phils and Cubs Swap Talented Center Fielders

The Deal: Phillies trade Dode Paskert to the Chicago Cubs in exchange for Cy Williams.

Dode Paskert was a very good center field, one that most people believed the Phillies should have been content with. Paskert was a good defender and had strung together a few fine seasons at the plate, and yet, the Phillies were willing to trade him for a relatively unknown center fielder.

That man was Cy Williams of the Chicago Cubs. He led the league in OPS in 1916, but after a slight decline the following season, the Cubs were ready to look for a more proven entity and acquired Paskert.

Williams would go on to spend 13 seasons as a member of the Phillies, and though he never accomplished anything too spectacular, he was a very consistent, very good player.

23. From Rival to Hero

The Deal: Phillies trade Mac Scarce, John Stearns, and Del Unser to the New York Mets in exchange for Tug McGraw, Don Hahn, and Dave Schneck.

In hindsight and with all of Tug McGraw's accomplishments in a Phillies' uniform, including the 1980 World Series title, in mind, to some, calling this trade "controversial" would be equivalent to blasphemy, but my, how quickly we forget.

McGraw was once a member of the New York Mets, bitter rival of the Phillies, helping the club's arch-rival to the top of the National League.

Even after the closer was ready to change allegiances in the trade, the Phillies were going to pay the price. They were sending valuable bench player Del Unser to the Mets (though he'd eventually return to the Phillies,) along with the second overall pick of the 1973 draft, John Stearns.

Stearns would become a four-time All-Star for the Mets, but I think it's safe to say this trade worked out well for the Phillies.

22. Phillies Make a Move for Morgan

The Deal: Phillies trade Mark Davis, Mike Krukow, and Charles Penigar to the San Francisco Giants in exchange for Joe Morgan and Al Holland.

Though he was at the back end of his career, Joe Morgan was still a very good player. He was still a very good player, but he wasn't getting any younger.

After dealing second baseman Manny Trillo in the infamous "five-for-one" deal for Von Hayes, the Phillies were in need of a second baseman and acquired the 39-year-old future Hall of Famer from the San Francisco Giants.

A lot of people questioned whether it was worth second young talent like Mark Davis and Mike Krukow to the Giants for an aging middle infielder.

While Morgan was actually very productive, one could argue that the best value in the deal, from a Phillies' perspective, was Al Holland, who would eventually assume the closer's role for the Phillies and became one of the best relievers in the history of the organization.

Neither could push the "Wheeze Kids" over the top.

21. The End of the Larry Bowa Era at Shortstop

The Deal: Phillies trade Larry Bowa and Ryne Sandberg to the Chicago Cubs in exchange for Ivan de Jesus.

Believe it or not, the aspect of this deal that made it controversial was not the fact that the Phillies included talented second baseman Ryne Sandberg. In fact, Sandberg was relatively unheard of at the time of the deal.

The real controversy was the bitter separation between the Phillies and incumbent shortstop Larry Bowa, as the two sides tussled over everything from the dollar amount of his contract to playing time, until the front office had enough of the fiery, short-tempered shortstop.

The Phillies ended an era, sending the 12-year veteran to the Chicago Cubs for shortstop Ivan de Jesus.

De Jesus never amounted to much for the Phillies, spending just three seasons with the club. Bowa didn't do much for the Cubs either in just three and a half seasons. The gem of the trade was Sandberg, who would have a Hall of Fame career.

20. Lights out

The Deal: Phillies trade Michael Bourn, Mike Costanzo, and Geoff Geary to the Houston Astros in exchange for Brad Lidge and Eric Bruntlett.

After becoming the "team to beat" in 2007, the Phillies found themselves in a position to add a few pieces to their club heading into the off-season, and one of the biggest areas of concern for the club was the bullpen, which was sorely lacking a dominant closer.

"Dominant closer" weren't exactly a popular choice of words to describe Houston Astros' closer Brad Lidge, who had derailed a bit after allowing a walk-off, postseason home run to Albert Pujols. A lot of people thought he'd never recover mentally.

Not the Phillies.

The Phillies took a big chance on him by sending speedy center fielder Michael Bourn to Houston. The Lidge gamble paid off in full for the Phillies, as the closer converted each and every save of the 2008 season and helped the Phils win a World Series.

19. Abreu's Salary Dumped on Yankees

The Deal: The Phillies trade Bobby Abreu and Cory Lidle to the New York Yankees in exchange for Carlos Monasterios, CJ Henry, Jesus Sanchez, and Mike Smith.

The Phillies had to trade Bobby Abreu. Everyone knew it was coming. He had publicly voiced his displeasure with the direction of the organization (of course, he was very wrong about his displeasure) and most with knowledge of the situations suspected that he was having a negative impact on the clubhouse.

What wasn't expected was that the Phillies would simply dump his contract on another club.

Though he was expensive, Abreu was a very good player at the end of his Phillies' tenure, and many expected a pleasant return of prospects in exchange for him.

Instead, the Phillies accepted mediocre prospects from the New York Yankees, who in turn ate all of Abreu's salary, in what was your prototypical salary dump.

At the time of the deal, it was a controversial move, and some wondered whether or not the Phillies would ever be serious about contending.

18. Houston, We Have Liftoff

The Deal: Phillies trade JA Happ, Anthony Gose, and Jonathan Villar to the Houston Astros in exchange for Roy Oswalt.

By the 2010 trade deadline, the Phillies had already made two big trades for Roy Halladay and Cliff Lee that left their farm system looking thin, but after failing to capture the World Series the previous season, the club needed a boost for their next run.

First and foremost, they needed to decide just who they wanted. The two names that found themselves in rumors leading up to the deadline were Roy Oswalt and Dan Haren, and some people believed that Haren was the better value.

However, the Los Angeles Angels landed the former Arizona Diamondbacks' ace, and the Phillies decided to make their move for Oswalt, sending three talented players to the Houston Astros.

JA Happ had become a fan-favorite, while Anthony Gose had very high potential, and Jonathan Villar was an under the radar prospect. That's where the controversy existed.

For comparison's sake, Baseball America rated Gose as the Toronto Blue Jays' top prospect heading into 2012, and Villar is in the Astros' top 10.

17. From Top Prospect to Trade Bait

The Deal: Phillies trade Gavin Floyd and Gio Gonzalez to the Chicago White Sox in exchange for Freddy Garcia.

After struggling for more than a decade, the Phillies wanted to make a splash at the MLB level, and fast. After signing players like Jim Thome and David Bell to big contracts in recent seasons, the Phillies decided that they needed pitching, and the best way to get it was by promoting first round draft pick Gavin Floyd.

Several executives were against the idea, believing that Floyd was being rushed to the MLB. He struggled mightily and the Phillies' brass soured on him quickly.

Hoping to salvage some of his value, the Phillies packaged Floyd with fellow pitching prospect Gio Gonzalez and sent them to the Chicago White Sox in exchange for Freddy Garcia, former ace of the Seattle Mariners.

Both Floyd and Gonzalez went on to have relatively successful MLB careers, while Garcia made just 11 starts for the Phillies and won one game.

16. Ruben Amaro's "Extra Free Agent Year" Tendency

The Deal(s): Phillies sign free agent Jamie Moyer to two-year, $13 million contract. Phillies sign free agent Placido Polanco to three-year, $18 million contract. Phillies sign free agent Raul Ibanez to three-year, $30 million contract.

Given the Phillies' success, it's kind of hard to file many grievances against him as a general manager, but I've found a way to compile most of (if not all) of his bad decisions into one slide, which I'm tentatively calling, "Ruben Amaro Jr.'s Extra Free Agent Years."

After all, that's the most controversial part of his tenure.

Even after Philadelphia became a destination for baseball players, Amaro continues to overpay for free agents, giving them an extra, guaranteed year on their contracts which, more often than not, becomes a huge hindrance for the Phillies.

The short list consists of Jamie Moyer, Placido Polanco, Raul Ibanez, and possibly Jonathan Papelbon. All would have been good deals with one less year on their deal. All look worse than they actually were because of that unnecessary year.

15. A Pretty Good Plan B

The Deal: Phillies trade Carlos Carrasco, Lou Marson, Jason Donald, and Jason Knapp to the Cleveland Indians in exchange for Cliff Lee.

Roy Halladay was the guy that the Phillies really wanted, but after finding themselves unwilling to meet the demands of the Toronto Blue Jays, the front office moved on to Plan B, and it was a fine Plan B indeed.

After several weeks of rumors that the Phillies were unwilling to move their top pitching prospect, Kyle Drabek, for Halladay, the Phillies moved four other prospects to the Cleveland Indians for Cliff Lee.

Though many liked the former American League Cy Young's chances moving into the NL, the Phillies paid the price. Carlos Carrasco was a top talent, and the Phillies believed that Lou Marson and Jason Donald would become big parts of their future, let alone, 19-year-old Jason Knapp, who had one of the organization's better fastballs.

This is another deal that worked out quite well for the Phillies in hindsight.

14. Scott Rolen to "Baseball Heaven"

The Deal: Phillies trade Scott Rolen to the St. Louis Cardinals in exchange for Placido Polanco, Bud Smith, and Mike Timlin.

After several seasons of being the lone bright spot for the Phillies, Scott Rolen was fed up. Though there were reinforcements on the horizon, he wanted out of Philadelphia and the organization was happy to oblige.

The controversy in this deal was two-fold.

First and foremost, Rolen kicked up a bit of a stir on his way out the door by calling St. Louis "baseball heaven," something that Phillies' fans didn't take kindly to and will never forgive him for.

However, the Phillies caused a stir themselves in some realms of the baseball world by accepting a less-than-acceptable return for the All-Star third baseman.

After throwing a no-hitter for the Cardinals, Bud Smith became a huge bust for the Phillies, and Mike Timlin made just 30 appearances. Placido Polanco was the best player in the deal, and the Phillies were forced to deal him to make room for Chase Utley.

13. Schilling Becomes a Snake

The Deal: Phillies trade Curt Schilling to the Arizona Diamondbacks in exchange for Vicente Padilla, Travis Lee, Omar Daal, and Nelson Figueroa.

At the time of this deal, the Phillies had already begun developing a strong farm system. Several times they had the opportunity to build on that system, and instead, added several replacement level players in exchange for a star.

This time, it was Curt Schilling who wanted out.

After leading the Phillies to the World Series in 1993, Schilling wanted out as we moved into a new millennium, and the Phillies sent him to the Arizona Diamondbacks for an incredibly boring haul.

Vicente Padilla would prove to be most valuable for the Phillies, as players like Travis Lee, Omar Daal, and Nelson Figueroa merely held down the fort until the Phils' top prospects were ready to take over.

12. Ace Swap

The Trade: Phillies trade Rick Wise to the St. Louis Cardinals in exchange for Steve Carlton.

This deal had a bit of controversy from both organizations involved.

The Phillies had been unable to agree to terms on a new contract with their ace, Rick Wise, and reportedly called a few teams to make his availability known. The St. Louis Cardinals had done the same thing with their ace, Steve Carlton, who had ticked off ownership with his attitude and contract demands.

Naturally, both teams thought a change of scenery would be nice, but would it be worth it for either club?

Did the Phillies really want to take on a headcase that was already requesting more money, when Wise had thrown a no-hitter (and hit two home runs in the same game?)

Needless to say, they're glad they did.

11. The Phillies Get Their Man

The Deal: Phillies trade Kyle Drabek, Travis D'arnaud, and Michael Taylor to the Toronto Blue Jays in exchange for Roy Halladay.

Finally, the Phillies got their man, but he didn't come cheap.

After months of pursuing Roy Halladay, the Phillies finally got the Toronto Blue Jays to part with their ace, so long as the Phils were willing to part with their top pitching prospect, and they were.

Yet again, it hardly seemed like a risky proposition on the surface, given Halladay's track record. However, the Phillies were moving several of their top prospects for Doc's services, all three of which would be ranked in another organization's top 10 in the future.

As it turns out, the gem of the deal may have been Travis D'arnaud, who the Phillies supposedly tried to reacquire this winter.

Of course, this deal was controversial not only because of the talent the Phillies were parting with, but the other deal that made this one possible as well.

10. Pence Gives Phillies' Offense a Spark

The Deal: Phillies trade Jonathan Singleton, Jarrod Cosart, Domingo Santana, and Josh Zeid to the Houston Astros in exchange for Hunter Pence.

The Phillies had been eying right fielders for quite a while by the time the 2011 trade deadline rolled around. After Jayson Werth left for the Washington Nationals in free agency, he left a void that the Phillies never filled internally.

A sense of urgency seemed to wash over the fan base as the San Francisco Giants landed Carlos Beltran—one of the Phillies' rumored targets. 

However, we now know that the Phillies had their eye set on a different right fielder: Houston Astros' slugger Hunter Pence.

The Phillies paid a ton for the outfielder, sending their best hitting and pitching prospect to the Astros, as well as the talented Domingo Santana.

To date, Pence has been the perfect fit for the Phillies, but that doesn't change the price that they paid to get him, which some people still believe was too much.

9. Charlie Hustle to the Bank

The Deal: Phillies sign free agent Pete Rose to four-year, $32 million contract.

Heading into free agency, there was no questioning Pete Rose's resume. He was the owner of multiple World Series rings, a Rookie of the Year Award, an MVP Award, and 12 All-Star appearances. The real question was: Are the Phillies in a position to sign him?

The club had just dropped three straight National League Championship Series, and a lot of people, including ownership, questioned their will to win.

That's why they wanted Rose—a proven winner.

So the decision was made, the Phillies offered Rose a deal that would make him the highest paid free agent in the history of baseball at the time, and he accepted.

The Phillies missed the postseason in 1979, making the deal look dubious, but in 1980, it all paid off.

8. The Return of Cliff Lee

The Deal: Phillies sign free agent Cliff Lee to five-year, $125 million contract, with club option for a sixth year at $27.5 million.

After trading him to the Seattle Mariners, most Phillies fans thought that they had seen the end of Cliff Lee with the Phillies, and boy, they were not happy about it. The pain was made worse by having to sit on the sidelines and watch the New York Yankees court him.

Of course, the Phillies weren't sitting on the sidelines at all.

Instead, they waited for the perfect moment, striking at the last possible moment to land Lee for a second time.

Fans were thrilled, but not everyone shared the sentiment. The Phillies are paying Lee a huge amount of money into his late 30s, and there are some people who believe that contract option could be an albatross.

Phillies fans may be thrilled now, but will the feeling last?

7. Phillies Bring Thome to Town

The Deal: Phillies sign free agent Jim Thome to six-year, $85 million contract.

It's hard not to love Jim Thome. The man is as great a person as he is a baseball player, and as a baseball player, he's bound for the Hall of Fame.

With that being said, however, it's also easy to not love the contract that the Phillies dolled out for him prior to the 2003 season.

The Phillies had their reasons to pay the man. First and foremost, he was still one heck of a ball player. In his last season with the Cleveland Indians, Thome hit 52 home runs and led the league in OPS. He was also expected to draw fans back to the ballpark, and then into the brand new Citizens Bank Park the following the season.

However, most baseball experts knew that the huge commitment would be a burden on the Phillies' payroll, and sure enough, it was. With Ryan Howard knocking on the door in the coming years, the team was forced to trade Thome to the Chicago White Sox and would wind up paying off part of his contract for several years.

6. The Jonathan Papelbon / Ryan Madson Saga

The Deal: Phillies sign free agent Jonathan Papelbon to four-year, $50 million contract, plus $13 million vesting option.

One thing was certain heading into the off-season prior to the 2012 season: The Phillies wanted a veteran closer at the back end of their bullpen.

A second thing quickly became clear as well: The Phillies didn't consider Ryan Madson a "veteran closer."

Though the Phillies thought very highly of him, the Phillies didn't view Madson in the same light as Jonathan Papelbon, despite being rumors to have offered him a four-year, $44 million contract option to keep him aboard. They didn't.

That was only the first half of the controversy.

The Phillies then agreed to a new contract with Papelbon, paying him $50 million over four years to become the second highest paid reliever in the history of baseball, something that most baseball pundits immediately recognized as a risky proposition.

All of that, and Papelbon hasn't thrown a single pitch as a member of the Phillies yet.

5. Five-for-One

The Deal: Phillies trade Manny Trillo, Julio Franco, George Vukovich, Jay Baller, and Jerry Willard to the Cleveland Indians in exchange for Von Hayes.

Talk about a risky proposition.

The Phillies were infatuated with the possibility of acquiring Von Hayes, so much so that they sent five players to the Cleveland Indians in exchange for the former seventh round draft pick who had just posted an OPS of just .699 in the previous season.

The deal included fan-favorite and valuable second baseman Manny Trillo, as well as Julio Franco, who would have an extremely lengthy MLB career, and George Vukovich, who was considered a promising player.

The Phillies were willing to risk a lot for Hayes, a player they believed the future of their franchise could be built around. Though he turned out to be a solid player, Hayes was never the perennial All-Star that some thought he could be, and truthfully, hardly worth five players of any caliber.

4. Fed Up with Allen, Phillies Trade Him

The Deal: Phillies trade Dick Allen, Jerry Johnson, and Cookie Rojas to the St. Louis Cardinals in exchange for Byron Browne, Curt Flood, Joe Hoerner, and Tim McCarver. After Flood refused to report to the Phillies, the Cardinals send Willie Montanez and Jim Browning to the Phillies.

What a mess of a deal.

After signing him as an amateur free agent several years prior, the Phillies knew that they had one heck of a player in Dick Allen, but were thoroughly fed up with his off-the-field antics. Afraid they'd keep him from becoming the player he was capable of becoming, the Phillies explored deals for the troubled infielder.

The St. Louis Cardinals were ready to make a deal, and offered the Phillies a number of talented players, including outfielder Curt Flood. The Phillies also received Joe Hoerner in the deal, who would be dominating out of the bullpen, a solid catcher in Tim McCarver and Byron Browne.

That's where the trouble began.

Flood refused to report to the Phillies, who had already agreed to the deal. Therefore the Cardinals were forced to send different players in the deal, which is how the Phillies received Willie Montanez and Jim Browning.

The sheer size of the deal had pundits questioning whether or not it was worth it, and after watching Allen excel with other clubs, those questions were well placed. All things considered, the Phillies probably didn't receive fair value for the future MVP.

3. Phillies Overpay Eaton

The Deal: Phillies sign free agent Adam Eaton to three-year, $24 million contract.

What inspired the Phillies to even think about offering Adam Eaton this contract? I still wonder what the answer to that question is to this day. Just stop for a moment and picture what the conversation was like in the front office:

"What were Eaton's numbers like last season?" "Well, he only made 13 starts, posted a record of 7-4, and had an ERA of 5.12." "Sounds great! Give him a three-year, $24 million deal!"

Don't even try and support his case with advanced metrics. It can't be done.

People around the game hated the deal from a Phillies perspective, and Eaton only managed to prove them right, failing to make it through the second guaranteed year of his deal, forcing the Phillies to do something they rarely do; something you have to be really bad to force them to do—cut him.

The man was booed as he was receiving his World Series ring. If that doesn't tell you about his case, nothing will.

2. Big Piece, Big Money

The Deal: Phillies extend the contract of Ryan Howard for five-years, $125 million, with club option for a sixth year at $23 million.

On one hand, extending Ryan Howard's contract made some sense. Howard was in the prime of his career and in the midst of a 45 home run season. The idea in extending his contract was to keep the former MVPs price down by keeping him out of free agency, where he'd compare (in some sense) with fellow first basemen like Albert Pujols, Prince Fielder, and Adrian Gonzalez.

As it turns out, by doing so, the Phillies actually overpaid for him.

Though Ruben Amaro Jr. will play it off as though he got Howard on a five-year commitment, because there were two years remaining on his contract, it was much more like a seven-year commitment, and the Phillies are drastically overpaying the declining first baseman over those last five seasons.

That isn't to say that Howard isn't still a good first baseman, but the deal was met with a lot of criticism and as we progress into the extension, it only looks as though the criticisms that created this deal's controversy will be proven right.

1. Cliff Heads West

The Deal: Phillies trade Cliff Lee to the Seattle Mariners in exchange for Phillippe Aumont, Tyson Gillies, and JC Ramirez.

Easily the most controversial move the Phillies have ever made.

First and foremost, most people couldn't fathom the idea of trading Cliff Lee. After acquiring him, he breezed through the regular season and ran roughshod through the postseason, and to put the cherry on top, he was very affordable in 2010.

However, the Phillies didn't think they could afford to keep him long term. On the other hand, Roy Halladay was willing to sign a very favorable extension with the Phillies, who in turn, were not confident in their farm system with both pitchers aboard.

So the Phillies pulled the trigger on the Halladay deal, landing the ace they had their eye on all along while also (seemingly) pulling the trigger on Lee's Phillies career.

The fan base was appalled, as was Lee, and Ruben Amaro Jr. defended the move by citing the need to replenish the farm system while pointing towards his new catch as the rotation's ace.