25 Greatest Philadelphia Phillies Offseason Moves of All Time

Every offseason move is made with the intention of helping a club win a World Series title.

That's a wide spectrum, and things don't always seem to work out that way, but it is certainly the intention. Whether teams add a home run hitter, an ace starting pitcher or depth to their bench, the goal is to win a World Series. 

So, when teams actually win the World Series, those moves are looked back on with favor. And when they come up short, the general manager made a mistake. That's just the way the game works. 

But the Philadelphia Phillies have had at least one of those moves on each end of the spectrum and everywhere in between. This slideshow will take a look back at offseasons of Phillies past and determine the best transactions. 

Remember, these transactions had to have taken place in the offseason. Once the regular season begins, those transactions are off limits. In an attempt to keep the discussion relevant, I focused on every offseason since the dawn of free agency as we know it. 

25. Jim Eisenreich

You can look at the Phillies' acquisition of Jim Eisenreich in one of two ways. The first is that they overpaid for him and he didn't produce nearly as much as anticipated—and I wouldn't push the argument too hard if that's how you felt. 

That's not how I feel about it, though. Eisenreich was invaluable to the Phillies' World Series run in 1993 because of his versatility, and that was a constant over his four-year tenure. 

When all was said and done with the Phillies, Eisenreich had hit .324 and posted an OPS of .833. In my opinion, the Phillies got exactly what they paid for—and then some.

24. Doug Glanville

Doug Glanville has to be one of the most underrated outfielders in Phillies franchise history. 

Drafted by the Chicago Cubs in 1991, Glanville didn't make his MLB debut until 1996. The Cubs traded him following the 1997 season, swapping him with Phillies second baseman Mickey Morandini. 

Glanville had a very solid career with the Phils. He hit .276, slugged 49 home runs and stole 143 bases, all the while playing a very good center field.

23. Mitch Williams

The Phillies acquired Mitch Williams from the Chicago Cubs in April of 1991. They could have let him walk at the end of the season, but made a sound decisions in bringing him back. 

While he never matched his statistical success from the 1991 season with the Phillies, Williams played a huge role in stabilizing the club's bullpen. And while I'm sure it didn't end the way they intended, the Phillies may not have been able to reach the World Series in 1993 had it not been for Williams. 

In three seasons, he recorded 102 saves for the Phils. 

22. Manny Trillo

In February of 1979, the Phillies sent five players to the Chicago Cubs in exchange for three players that they hoped would help get them over the hump of the National League Championship Series. 

Among the players they received was slick second baseman Manny Trillo. 

While the Phillies missed the postseason in Trillo's first season as the club's second baseman, the man won a Gold Glove and started the most impressive portion of his career. Over the next few seasons, he added two more Gold Gloves and a pair of Silver Slugger awards, as well as three straight trips to the All-Star Game. 

The Phillies finally got over that NLCS hump in 1980 when Trillo put on a show against the Houston Astros and was named the 1980 NLCS MVP.

The Phillies also received Greg Gross and Dave Rader in the deal.

21. Von Hayes

It wasn't the greatest deal of all-time for the Phillies considering the simple fact that they sent five players to the Cleveland Indians for his services and he never lived up to the hype, but Von Hayes was an excellent player.

Julio Franco was the only other player in the deal to become anything of substance and had he not been involved, it would have been a much better looking deal for the Phillies. 

But Hayes was solid for the Phillies. He appeared in an All-Star Game and finished eighth in the league's MVP voting in 1986.

20. Aaron Rowand

When the Phillies traded Jim Thome to the Chicago White Sox prior to the 2006 season, it was a polarizing deal for the fans. Some thought that they should have gotten more. I personally believe that it was a solid deal. 

First and foremost, the Phillies had almost no leverage. Thome's deal was going to hurt them on the books for years to come, and it eventually did anyway. They had to get rookie sensation Ryan Howard into the lineup, and there was only one spot for him to play. 

So the Phillies traded Thome to the White Sox for center fielder Aaron Rowand, Gio Gonzalez and Daniel Haigwood. 

Rowand was a great pickup for the Phillies. The fans loved him because he played a hard-nosed style of ball, and Rowand responded by having two of the best years of his career, hitting 39 home runs, making his lone All-Star team and winning a Gold Glove.

19. Jim Lonborg

I feel as though every time I write about Jim Lonborg I have the urge to start with "probably not a name you'd expect," which should serve as a good indication of just how underrated he was as a Phillie. 

Lonborg won a Cy Young Award as a member of the Boston Red Sox and helped pitch them to the World Series in 1967.

He joined the Phillies later in his career. 

With his new club, Longborg won 75 games over seven seasons to the tune of a 3.98 ERA. He retired just before the Phillies won the World Series in 1980, but did help pitch the club into three consecutive NLCS from 1976-78.

18. Al Holland

They say closers are cut from a different cloth, and Al Holland was certainly cut from a different cloth. 

After successful stints with the Pittsburgh Pirates and San Francisco Giants, Holland turned things up to a new level when the Phillies acquired him from the Giants before the 1982 season (along with Hall of Famer Joe Morgan). 

In two-and-a-half seasons, Holland saved 55 games for the Phillies, appeared in an All-Star Game and finished sixth in the 1983 Cy Young voting. 

17. Ron Reed

Tug McGraw gets a lot of the publicity about the glory days of the Phillies bullpen thanks to his closer-oriented antics, but what a lot of casual fans fail to realize is that he was only one half of a dynamic one-two punch. 

That other half was Ron Reed, acquired from the Atlanta Braves as a starting pitcher prior to the 1976 season and converted into a very good reliever by the Phillies. 

He saved nearly as many games as McGraw (90), and though he never appeared in an All-Star Game, he too played a role in getting the Phillies to the World Series in 1980 (although, not nearly as large as the role his teammate played). 

Reed was an excellent member of the Phils bullpen for eight seasons.

16. Gary Matthews

You don't get to have a nickname like "Sarge" without being a little terrifying, and Gary Matthews was certainly such a player. He was just the kind of presence that the Phillies needed after their World Series run in 1980. 

The Phillies acquired Matthews from the Atlanta Braves in March of 1981 in exchange for starting pitcher Bob Walk. 

It was a very good deal for the team. Though Matthews spent just three seasons with the Phillies, he received consideration for the MVP award twice and hit 38 home runs, helping the club back to the World Series in 1983.

15. Pete Rose

When the Phillies signed Pete Rose before the 1979 season, they made him the highest paid free agent of all-time, so they certainly did not get a bargain. 

But after watching him dominate the National League as a member of the Cincinnati Reds for years, the Phillies were more interested in one of Rose's intangibles: He knew how to win. 

After three straight losses in the National League Championship Series, the Phillies put the pressure on Rose to teach the "Fightins" how to win. After a brief relapse in 1979, the Phillies won it all in 1980. 

14. Jim Thome

The Phillies broke the bank to bring free-agent slugger Jim Thome prior to the 2003 season, and most pundits believed that they overpaid for him. And they did. It was a necessary evil if they were going to lure a big free agent to Philadelphia. 

The Phillies teased Thome with the promise of a young core coming through the farm system and a brand new ballpark on the horizon that would change baseball in the city of Philadelphia forever—and both came true. 

Thome did his part, hitting 96 home runs over parts of three seasons for the Phils, helping to revitalize baseball in South Philly. 

So while the club overpaid for his services, there is no doubt that bringing Thome to Philadelphia was a huge positive for not only the Phillies, but the city as well.

13. Steve Bedrosian

If the Phillies have been good at anything in the offseason, history shows that it is getting good closers in a trade and having them perform at elite levels, like Steve Bedrosian winning the Cy Young award in 1987. 

The Phillies received Bedrosian alongside Milt Thompson (who would also be a contributor for years to come) when they sent Pete Smith and Ozzie Virgil to the Atlanta Braves. 

In addition to his Cy Young Award, Bedrosian also appeared in an All-Star Game for the Phillies and recorded 103 saves. 

12. Cliff Lee

Signing Cliff Lee before the 2011 season was probably one of the best and worst offseason moves in Phillies history, but I'll look at the downside of this move in a different slideshow. 

From the "best" perspective, we're talking about one of the game's elite starting pitchers, who left millions of dollars on the table to return to Philadelphia. Without that concession, this move wouldn't have been possible. 

Even though the win total doesn't show it, Lee has turned in two stellar seasons in the first two years of his new contract with the Phillies and doesn't appear to be slowing down any time soon.

11. Jimmy Rollins

By the time Jimmy Rollins hit free agency following the 2011 season, he had been playing shortstop for the Phillies for so long that it would have seemed weird to have someone else playing there. 

The Phillies made the right decision to bring him back. 

That's not to say that they didn't have options. At the time, Chase Utley was expected to be healthy and Freddy Galvis could have stepped right in and played an incredible defensive shortstop. 

But the Phillies wound up getting Rollins at a good price ($11 million per year) for an elite shortstop. He may not be suited for the top of the order at this point in his career, but I struggle to think of a team that wouldn't want an above average defensive shortstop with 20-home run power.

10. Brad Lidge

Brad Lidge's tenure with the Phillies was an interesting one highlighted by a tremendous peak and a trip to rock bottom. 

The Phillies acquired him from the Houston Astros before the 2008 season in exchange for speedy outfielder Michael Bourn and a couple of throw-ins. The hope was that he would stabilize the bullpen by being lights-out in the ninth inning. 

Boy, did he. 

Lidge was perfect in 2008, and the Phillies' pitching staff was much better as a result. His contract was extended during the season, which culminated in a World Series title. 

The next three seasons were marred by injuries and poor performances, but most Phillies fans still claim that it was all worth it for that single moment in October of 2008.

9. Shane Victorino

In its history, only a handful of Rule 5 draft picks have gone on to become All-Star caliber players. Shane Victorino may be the luckiest of the bunch considering that he was selected in the draft twice. 

The second time around, the Phillies drafted him from the Los Angeles Dodgers and kept him aboard as a speedy fourth outfielder. When the Phillies traded Bobby Abreu, Victorino took over in right field and his career escalated quickly. 

Now, Victorino is a two-time All-Star and Gold Glove winner. 

8. Billy Wagner

His exit made him a villain, but the Phillies made an excellent deal when they sent very little to the Houston Astros for two seasons of Billy Wagner prior to the 2004 season. 

In just two seasons with the Phillies, Wagner thrilled fans by lighting up the radar gun and saving 59 games. He made one trip to the All-Star Game in 2005 when he led the league in games finished with 70. 

7. Roy Halladay

Any time you can get a pitcher like Roy Halladay in a trade and have him sign a team-friendly contract extension, you pull the trigger on that deal. And so far, it has been a good one for the Phillies. 

They sent plenty of talent to the Toronto Blue Jays in return for Halladay's services, but the ace has turned in two elite seasons and a good one for the Phillies in his first three years with the club. 

Halladay has pitched a perfect game, a no-hitter, won a Cy Young award and appeared in two All-Star Games. Not a bad body of work for just three seasons. 

6. Tug McGraw

I'm not sure the Phillies knew exactly what they were getting into when they acquired Tug McGraw from the New York Mets prior to the 1975 season. For nine years, he had been the enemy—a Met. He helped the Phillies' rivals to a World Series title in 1969 and left the Phillies faithful green with envy. 

Needless to say, worlds were turned upside down when the Phillies sent three players to the Mets in exchange for McGraw, John Stearns and Dave Schneck. 

But history shows that it was a great deal. Stearns would turn out to be a good catcher for the Mets, but McGraw was one of the best closers in Phillies history. He saved 94 games, pitched out of the bullpen for 10 seasons, appeared in two All-Star Games and helped the Phils win their first World Series in 1980.

5. Jim Bunning

The Detroit Tigers thought that Jim Bunning was heading into decline and wanted to cash out as quickly as possible, so the Phillies got on the phone and swung a deal for the right-handed pitcher (along with catcher Gus Triandos) in exchange for Don Demeter and Jack Hamilton. 

The deal looked great for the Phillies right away. Bunning won 19 games in his first season as the Phillies' ace and pitched a perfect game against the New York Mets on Fathers Day. 

He spent four seasons in Philadelphia before they cashed out on him as well, though he rejoined the Phils for two years at the tail end of his career. In total, Bunning spent six seasons and 89 games with the Phillies as a two-time All-Star.

4. Johnny Callison

This is easily one of the best offseason moves in Phillies history. 

The 1960s was not a good decade for the Phillies, and positive aspects are hard to come by. But if you ask people what they remember about the Phillies in the 1960s in that light, Johnny Callison will be the overwhelming majority. 

Acquired from the Chicago White Sox in exchange for Gene Freese, Callison stepped up to become the face of the Phillies franchise for the next decade. 

He was loved for his hustle, athleticism and personality, and that's without mentioning the fact that he was a three-time All-Star for the Phillies as well.

3. Curt Schilling

Curt Schilling, who was acquired on the day before the 1992 regular season began, barely met the requirements to be on this list. But I think we'll allow a little wiggle room for one of the best pitchers in franchise history.

The Phillies acquired Schilling from the Houston Astros as they trimmed down their roster, sending pitcher Jason Grimsley to Houston in return.

In hindsight, it was an excellent move for the Phillies. Schilling went on to anchor the starting rotation as soon as 1993, helping lead the Phillies to a World Series berth. He won 101 games for the Phils and appeared in three consecutive All-Star Games for them from 1997-99. 

2. Bobby Abreu

Love him or hate him, this may be the biggest steal on the entire list. 

Bobby Abreu's career with the Houston Astros ended when they allowed him to go to the Tampa Bay Rays in the Rule 5 draft. Little did the Rays know that they were on to something. 

Or did they? 

The Rays turned and quickly dealt Abreu to the inquiring Phillies, who had to give up infielder Kevin Stocker to facilitate the trade. It was a deal they would make 100 times over. 

While his approach and attitude were questionable at times, there is no doubt that Abreu became one of the greatest hitters in franchise history. He hit .303, posted an OPS of .928, stole 204 bases and slugged 195 home runs. 

Abreu was a two-time All-Star, Gold Glove, Silver Slugger and Home Run Derby winner for the Phillies.

1. Steve Carlton

When you trade a pitcher who is supposed to be the ace of your staff in the offseason, you had better be getting someone stellar back in return. The odds of that aren't good, and fans were understandably weary about dealing Rick Wise to the St. Louis Cardinals. 

But I'd go out on a limb to say it was worth it in the end. After all, the Phillies received left-handed pitcher Steve Carlton in return. 

The deal was facilitated thanks to money and stubborn owners and players. Both Carlton and Wise wanted more money, and neither the Cardinals nor Phillies wanted to give either man a raise. So they swapped pitchers. 

Carlton's impact was felt immediately in Philly. He won 27 games in the first of his 15 seasons with the Phillies that would build the bulk of a 300-plus-win career. Carlton was a four-time Cy Young winner, seven-time All-Star and he even won a Gold Glove award. 

And of course, he helped pitch the Phillies to a World Series title in 1980.