Philadelphia Phillies: Ranking 25 Boldest Moves in Franchise History

Nothing says "off-season" quite like being bombarded by an onslaught of bizarre and seemingly impossible trade and free agent rumors, only to learn that some of them are actually much more concrete than a simple rumor: they're real. 

The Philadelphia Phillies know a thing or two about deals that sound so absurd they must be false, but, well, aren't. Over the last few seasons alone, they haven't limited themselves to the winter months to strike such a deal. They've made big trades during the season, signed big free agents during the winter, and shocked the baseball world with their savvy negotiations.

Simply put, they've made some bold moves.

This trend is not new, however. Throughout the history of the Phillies' franchise, they've been making some pretty bold statements. As we sit and ponder the next big transaction, let's take a look to the past. Here are the boldest transactions in the history of the Phillies: some good, some not so much.

But First, What Exactly Is a "Bold" Move?

To make this list a bit more comprehensive and encompassing, let's define a set of criteria to distinguish "bold" moves before we get into this list. Here are some of the criteria that were considered to rank the boldest moves in Phillies' history:

Star Power: How talented were the players being traded?

Size of Deal: For trades, how many players were being moved? The bigger, the bolder.

Money: How much money was involved? At the end of the day, money rules. Did the Phillies have to throw boatloads of money at a free agent to get him to sign? Was the trade a salary dump? Was the deal cost effective?

Risk Factor: Any deal that sees a team assume more risk is a bolder deal.

Impact: How much of an impact would the impending transaction have on the franchise, either good or bad?

25. A Salute to the Secretary of Defense

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

Playing their home games in a spacious outfield, the Phillies have preferred defensively adept center fielders for a long time. That was no different in 1975, when the Phillies traded a talented, yet under-performing outfielder, Willie Montanez, to the Giants in exchange for a supreme defender in Garry Maddox.

The Phillies were moving a promising outfielder for a great, five-tool player. Some risk, but not much. Regardless, a bold move.

24. Phillies Flip Paskert for Williams

The Deal: The Phillies acquire Cy Williams from the Chicago Cubs in exchange for Dode Paskert.

On the surface, this doesn't seem like a very bold deal. After all, these two clubs were just swapping a pair of center fielders, right?

Wrong.

In Dode Paskert, the Phillies already had a good center fielder, and he was much more accomplished than the Cubs' young center fielder, who went by the name of Cy Williams. However, the Phillies saw something they liked in Williams and offered the Cubs Paskert in exchange for his services. They accepted.

Williams would go on to spend 13 seasons as a member of the Phillies, becoming one of the greatest players in the history of the organization.

23. Sure, You Can Have Ryne Sandberg

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

Larry Bowa's time was running out as a member of the Phillies. After clashing with the front office over what he was worth to the club, all parties decided it was best that he move on, and the Phillies found their replacement shortstop in Ivan de Jesus.

However, the Cubs, led by former Phillies' manager Dallas Green, now the general manager in Chicago, were not willing to complete a straight up swap. Instead, he requested an additional, young player with upside, and chose from a list that included none other than future Hall of Fame second baseman Ryne Sandberg.

Talk about bold.

22. The Complete and Utter Failure of Freddy Garcia

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

Yes, that actually did happen.

After spending years in the American League as a top of the rotation starting pitcher for both the White Sox and Seattle Mariners, the Phillies decided to take a chance on Freddy Garcia in his contract year as their rotation's anchor. As it turns out, because of injuries, he would make just 11 starts for the Phillies and win just one game.

On the other hand, the Phillies traded two very good pitchers. Gavin Floyd would go on to become a mainstay in the White Sox's rotation, and Gio Gonzalez would eventually become an ace of sorts for the Oakland Athletics.

21. Phillies Acquire Manny Trillo, Two Others

The Deal: The Phillies acquire Manny Trillo, Greg Gross, and Dave Rader from the Chicago Cubs in exchange for Henry Mack, Derek Botelho, Barry Foote, Jerry Martin, and Ted Sizemore.

Obviously, the first thing that sticks out about this deal is the size. The Phillies and Cubs agreed to a massive eight-player trade and each team would go on to benefit in different ways.

For the Phillies, the benefit was obvious. In Manny Trillo, the team acquired the second baseman they had been seeking for quite some time. He was slick-fielding middle infielder who built a reputation of coming up with some clutch hits, particularly, during the 1980 postseason.

The Phillies also acquired another key piece to their 1980 championship team in this deal, however, when they acquired pinch-hitting specialist Greg Gross. He also built a reputation for himself by coming up with clutch hits, including several during the Phillies' run to the World Series, especially in the NLCS versus the Houston Astros.

20. "Ya Gotta Believe"

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

Though this was a big, six-player deal, in the long run, only one name stands out above the rest: Tug McGraw.

As the Phillies attempted to put together a contending team in the National League, they looked to their NL rivals, the Mets, in hopes of striking a deal. The biggest focus was the back end of the bullpen, and the Phillies found their man in McGraw.

After pitching with the Mets for 10 seasons, McGraw drove the final stake through their hearts by capturing the World Series title with the Phillies in 1980, coining his legendary phrase, "Ya Gotta Believe!" and rubbing the championship season right in the face of the Mets.

19. Phillies Acquire Jim Bunning, Gus Triandos

The Deal: The Phillies acquire Jim Bunning and Gus Triandos from the Detroit Tigers in exchange for Don Demeter and Jack Hamilton.

In hindsight, this is one of the most productive trades the Phillies have ever made. After the Tigers had soured on Jim Bunning, the Phillies were able to acquire him rather cheaply, sending Don Demeter and Jack Hamilton to the Motor City.

In exchange, the Phillies received a future Hall of Fame pitcher, who helped lead them towards the postseason in 1964, before his tired arm could carry the team no longer and the Phillies eventually collapsed.

He also managed to toss the first perfect game in the history of the franchise, on Fathers Day. His catcher on that day was none other than Gus Triandos.

18. Your Prototypical Salary Dump

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

It was no secret that Bobby Abreu wanted out of Philadelphia, but you would think that you'd be able to get at least one decent prospect for a five-tool player like Abreu. Obviously, that wasn't the case. In one of the most obvious salary dumps of all-time, the Phillies sent Abreu and Cory Lidle to the Yankees for four fringe prospects, none of whom would appear in the MLB with the Phillies, and none of whom are still in the Phils' organization.

However, there is a large contingent of people who believe that the departure of Abreu changed the clubhouse culture for good, and in the next season, the Phillies reversed their bad fortune by posting a winning record.

17. Phillies Acquire Future Hall of Famer Joe Morgan, Along with Al Holland

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

The Phillies found themselves in the market for a second baseman once again after agreeing to trade Manny Trillo in another massive deal, and with little offerings on the free agent market, they began analyzing different trade scenarios. One particular situation arose where the Phillies would be able to kill two birds with one stone.

They would go on to strike a deal with the Giants, acquiring future Hall of Fame second baseman Joe Morgan, as well as a great reliever in Al Holland.

Though Morgan was on the back-end of his career, he still found a way to be productive in his lone season with the Phillies, posting a high OBP, as was the norm for Morgan. When the deal was struck, he was the center piece with hopes of capturing another NL Pennant, and though that goal was accomplished, the Phillies came up short in the ultimate goal.

On the other hand, Holland may have been the more valuable player to the Phillies, in total. He spent a couple of excellent seasons in the back-end of the Phillies' bullpen, giving the club an excellent option as the careers of Tug McGraw and Ron Reed began to wind down.

16. Phillies Acquire "The Dude"

The Deal: The Phillies acquire Lenny Dykstra, Roger McDowell, and Tom Eden from the New York Mets in exchange for Juan Samuel.

Though Juan Samuel was a very dynamic, offensive player, the Phillies were looking to revamp their offensive attack as they prepared to make a run at the postseason, and thus, struck a deal with the Mets acquiring the vastly talented center fielder, Lenny Dykstra.

"The Dude" would go on to have a few MVP-caliber seasons for the Phillies, but his health and lack of production in other seasons marred his Phillies' legend.

Also coming to the Phillies in the deal was Roger McDowell, who is often overlooked. He had a couple of excellent seasons as a member of the bullpen, and played a pivotal role in its success.

15. Scott Rolen Gets His Wish

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

The Phillies were stuck between a rock and a hard place in regards to Scott Rolen because he made it very clear that he wanted out. He got his wish when the Phillies sent him to a place he called "baseball heaven," striking a deal with the Cardinals.

In the deal, the Phillies acquired a versatile infielder by the name of Placido Polanco (you may have heard of him), a young pitcher who threw a no-hitter and then could barely find the strike-zone in Bud Smith, and a reliever in Mike Timlin.

Needless to say, they could have done better.

14. Phillies Fleeced for Curt Schilling

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

When the Phillies were a really bad team not so long ago, a lot of good players wanted out. Curt Schilling was among their ranks. For that reason alone, it is unreasonable to expect a king's ransom, but for goodness' sake, at least acquire some talent for the future!

The Phillies traded a bona fide ace to the D'backs, in exchange for a pair of starting pitchers who would go on to ride the shuttle between the MLB and AAA in Nelson Figueroa and Omar Daal, and a below average first baseman in Travis Lee.

I shudder at the fact that Vicente Padilla was the most productive player for the Phillies that came over in that trade.

13. A Third Ace Joins the Fray

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

By this point in time, the Phillies and Astros knew each other well. The Astros were looking to sell off some of their remaining, valuable veterans and go into a full-blown rebuild, making Roy Oswalt available. Looking to push their pitching staff over the top down the stretch run and into the postseason, the Phils and Astros struck a deal.

The Phillies landed a third ace, and the Astros added a couple of interesting pieces to their system, including Phillies' starter JA Happ. Jonathan Villar joined the ranks of top Astros prospects and the club flipped Anthony Gose to the Toronto Blue Jays for Brett Wallace.

12. Fleecing the Indians?

The Deal: The Phillies acquire Cliff Lee and Ben Francisco from the Cleveland Indians in exchange for Carlos Carrasco, Lou Marson, Jason Donald, and Jason Knapp.

After moving on from their favored target, Roy Halladay, the Phillies set their sights on another ace, this time Cliff Lee of the Cleveland Indians. In his usual, under-the-radar fashion, Ruben Amaro Jr. struck a deal with the Tribe, bringing Lee to Philadelphia for four prospects.

Phillies' fans considered it a fleecing. The club had given up on Carlos Carrasco, viewed Lou Marson and Jason Donald as bench players, and saw Jason Knapp as being years away from impact on the MLB. They were right.

On the other hand, Lee has had an extraordinary impact on the Phillies' franchise. He led the club to the World Series in 2009 before being traded, but had already become a fan-favorite. Ben Francisco, the second player in the deal, has become a mainstay on the Phillies' bench.

11. Phillies and Cardinals Swap Aces

The Deal: The Phillies acquire Steve Carlton from the St. Louis Cardinals in exchange for Rick Wise.

There was an awkward situation brewing in both Philadelphia and St. Louis prior to the 1972 season. Neither team's ace was particularly happy with their contract situations, and thus, both teams decided that they would instead look to trade those pitchers. That created the ideal situation for a simple swap, and the Phillies and Cardinals did just that.

The Phillies assumed some risk in trading their ace, Wise, to the Cardinals, but knew they were getting an All-Star talent back to lead their club. That talent was, of course, Steve Carlton, who would go on to win four Cy Young Awards with the Phillies and lead them to the World Series in 1980.

10. Lights out

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

Acquiring Brad Lidge was a risk in and of itself. People around the game questioned his mental make-up after Albert Pujols had touched him up in the postseason and shattered his confidence. A change of scenery was in order, and the Phillies paid a relatively low price for his services.

Though Michael Bourn would go on to become an All-Star outfielder, Lidge would become a Philadelphia legend. In his first season with the Phillies, he didn't blow a single save, playing a pivotal, if not the most important, role on the 2008 World Series Phillies.

The addition of Eric Bruntlett flew under the radar, and though he wasn't nearly as important, he still played his role, scoring a couple of the most important runs of the World Series.

9. Good Game, Let's Go Eat

The Deal: The Phillies acquire Hunter Pence from the Houston Astros in exchange for Jonathan Singleton, Jarred Cosart, Domingo Santana, and Josh Zeid.

With Jayson Werth now a member of the Washington Nationals, the Phillies desperately needed to add some right handed power to the middle of their order, and did just that by making a deal with a favored trading partner, acquiring Hunter Pence from the Astros.

However, Pence's impact on the Phillies extended much further than that. He was an instant fan-favorite and re-energized a fading offense.

Contrary to popular belief, however, the Phillies were not taking advantage of the Astros. In Jonathan Singleton and Jarred Cosart, the Phillies were taking a big risk moving their top positional and pitching prospects, respectively. A third prospect, Domingo Santana, has tremendous upside.

There was a big risk involved for Pence.

8. Phillies Sign Pete Rose

The Deal: The Phillies sign free agent Pete Rose to a four year, $3.2 million contract.

When the Phillies signed Pete Rose prior to the 1979 season, they were already a good team. The problem was that there was a common theme growing amongst the Phillies—they didn't know how to win. Well, that was never a problem for Pete Rose, who was a part of the Cincinnati Reds' "Big Red Machine." 

So when "Charlie Hustle" hit the free agent market, the Phillies made the strongest push to sign him, and did. They temporarily made him the highest paid free agent of all-time, hoping that he would bring with him a winning culture, and he did.

7. Five-for-One

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

When you talk about teams assuming a huge amount of risk in a deal, this is it. The Phillies were trading five talented players for just one. Talk about putting all of your eggs into one basket. So when the Phillies sent five players to the Indians in exchange for Von Hayes, they expected him to be the next big thing.

He wasn't.

That isn't saying that Hayes was not a very good player, however. In fact, he was one of the greatest Phillies to have played the game. However, Hayes was billed as having the type of tool-set that results in a Hall of Fame career, and he was never the type of iconic player that pushed the franchise over the top.

6. The Doc Is in

The Deal: The Phillies acquire Roy Halladay from the Toronto Blue Jays in exchange for Kyle Drabek, Travis D'Arnaud, and Michael Taylor.

Even after acquiring Cliff Lee, it was no secret that Roy Halladay was the pitcher that the Phillies wanted. They wanted him to lead their starting rotation so much that they dealt Lee to the Mariners in order to re-tool a farm system that was about to take a hit, when they sent three top prospects to the Blue Jays to acquire Doc.

He wasn't coming cheap. Because they had been given a window to work out an extension the price in prospects was a hefty one. The Phillies were parting with Kyle Drabek, their top pitching prospect, and a top positional prospect in Michael Taylor. In 2011, Travis D'Arnaud has emerged as one of the Jays' top prospects.

With that being said, it is a deal the Phillies would make 100 times over. In his first full season with the Phils, all Halladay did was win the NL Cy Young Award, throw a perfect game, and toss a no-hitter in the postseason. He's posted a record of 40-16, and it is hard to get much better than that.

5. We Barely Knew Ye, Cliff

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

The Phillies made no bones about it: Roy Halladay was the guy they wanted. So when he became available, they sent Cliff Lee to the Seattle Mariners to re-tool the farm system. The fan-base was devastated and had Phillippe Aumont not figured things out in the bullpen in the Minor Leagues, this could have been one of the Phils' worst trades of all-time.

In hindsight, it actually was.

4. The Big Piece's Mega-Deal

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

When you talk about risky contracts, Ryan Howard has to be one of the first players to come to mind. It isn't hard to understand why the Phillies want to extend their sluggers contract in 2010, more than a year before he was slated to become a free agent.

At the time, Albert Pujols, Prince Fielder, Adrian Gonzalez, and Carlos Pena were all top sluggers that would be in play come the 2012 off-season, and with more markets that were eventually actually available in play, the Phillies wanted to lock him up. They were terrified that Pujols' deal (10 years, $250 million) would set the market for their first baseman.

They were taking a huge risk, and it will probably never pay off. Howard has had a number of injuries since signing his deal, and his production has been on the decline. However, it remains to be seen how much the damage ultimately is.

3. Moving on from Dick Allen; Denied by Curt Flood

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

Wow, what a complicated deal.

When the Phillies has soured on the attitude of Dick Allen, they looked to trade him. However, they knew they had an extremely talented player, and they wouldn't be trading him for cheap. The Cardinals stepped up and offered them a ton of talent, and the Phillies gladly accepted.

The only problem was that Curt Flood didn't want to play for the Phillies. He refused to report to his new club and the Cardinals were forced to send new talent to the Phils. (This mess would ultimately lead to free agency as we know it.)

One of the players that the Phils would receive in place of Flood would have a strong impact on the future of the franchise. The club acquired Willie Montanez, who would eventually be traded for Garry Maddox, who would eventually help the Phillies win the World Series.

2. A New Direction: Jim Thome

The Deal: Phillies agree to sign free agent Jim Thome for six years, $85 million.

The Phillies had been losing a lot of ball games for a long time by the time 2002 rolled around, but with a brand new ballpark on the horizon, the organization felt as though the time was right to go out and make a big splash. After years of spending little money and working like a small-market team, the Phillies made a big market move by bringing Jim Thome to town.

Thome, the market's top free agent, surprised the baseball world quite a bit by signing with the then-lowly Phillies. With his addition, the Phillies were able to change the entire dynamic of their offensive attack, and by proxy, many believe that the addition of Thome opened the door for a competitive Phillies' team of the future, now the present.

1. The Return of Cliff Lee

The Deal: Philadelphia Phillies agree to sign free agent Cliff Lee for five years, $125 million, with $27.5 million club option for 2016.

For what it was worth, anyone with a slight interest in the game of baseball had assumed that the Phillies had given up on Cliff Lee when the dealt him to the Seattle Mariners just a single off-season ago. However, under a veil of secrecy and and cult-like silence, the Phillies struck a with the market's top free agent.

In return to Philadelphia, Lee cited his interest in playing baseball with the Phillies often. However, it should be noted that the Phils were taking a bit of a risk by bringing the lefty back aboard. With Roy Halladay, Roy Oswalt, and Cole Hamels already under contract, they were tying up yet another large portion of the payroll in starting pitching.

As things would unfold, however, Oswalt would spend a lot of time on the disabled list during 2011, and Lee helped to give the Phillies' the best starting rotation in baseball.