20 All-Time Philadelphia Phillies Offseason Moves the Team Most Regrets

Greg PintoCorrespondent INovember 16, 2012

20 All-Time Philadelphia Phillies Offseason Moves the Team Most Regrets

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    Teams make offseason moves that they regret all of the time, especially in today's game. With millions of dollars on the line, some of these transactions can be described as a "necessary evil." 

    Poor offensive season the year before? Let's throw a ridiculous, exorbitant amount of money at the best free agent available and hope that he fixes all of our offensive problems. 

    It happens ever winter. The Philadelphia Phillies are no stranger to this scenario because they did it in their bullpen before the 2011 season. Trouble in the ninth inning? Throw a stupid amount of money at Jonathan Papelbon and hope he solves the problem. 

    The fact of the matter here is that it is easy to regret an offseason move. While this slideshow will take a look at some of the most regrettable offseason moves in Phillies history, it will only analyze the moves that have a reason to be regrettable. 

20. Pedro Feliz

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    I suppose this one is a bit debatable for a couple of reasons, the first being the simple fact that the Phillies were only tied to Pedro Feliz for two seasons (which is still one longer than they should have been). 

    Feliz was also a sensational defender for the Phillies over at third base. The real problem was that he wasn't nearly the offensive player that they expected him to be. 

    The Phillies let him walk following the 2009 season and he bounced around with a couple of MLB teams before signing with an independent league team. 

19. Kevin Milwood

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    There aren't many agents in the game that like to call a team's bluff, but Scott Boras has to be one of the few notorious for doing just that. 

    I don't think it was much of a secret that he wanted his client, Kevin Milwood, out of Philly in the worst way. He was set to become one of the better starting pitching options available following the 2003 season when he won 14 games, and naturally, his price was high. 

    The Phillies didn't think they'd be able to re-sign Milwood. It just didn't make much sense at the time, so they offered him arbitration in hopes of getting a couple of draft picks back. 

    As it turns out, the Phillies weren't the only team who thought Boras had overpriced Milwood. No team wanted to sign him for more than a year, so Boras had him accept a hefty one-year, arbitration deal from the Phillies before hitting the market again after 2004. 

    Milwood wasn't nearly as good  that season. 

18. Jim Thome

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    For the sake of clarity, we're not talking about Jim Thome's second deal with the Phillies. The glorious part of signing a bench player to a one-year deal is that even if it doesn't work out, it's manageable. 

    Thome's first deal with the Phillies was a bit more complex. With a new ballpark on the horizon, the ownership group wanted to make a splash and land a free agent that would draw fans. 

    Who better than Thome? 

    The Phillies threw a ton of money at the former Cleveland Indians slugger and all in all, he played well for them. The downside of the deal was that Thome was injured in 2005 and the Phillies replaced him with a younger, cheaper Ryan Howard. 

    In the offseason, they dealt him to the Chicago White Sox, but were still paying his contract years into the future. 

17. Jamie Moyer

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    Sure, Jamie Moyer is a pitcher that can be labeled "one of a kind," but it probably isn't a good idea to give a 45-year-old starting pitcher a multi-year deal—regardless of the circumstances. But the Phillies did. 

    Following their World Series title in 2008, new general manager Ruben Amaro Jr. re-signed Moyer to a two-year deal that would pay him $8 million a season. 

    Given the terms, it may not seem like it, but this was a big overpay. Moyer's value was inflated by a win total that he accrued with a lot of run support and he quickly began to wear down over the next two seasons, resulting in a Tommy John surgery in 2010.

16. Von Hayes

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    How can a deal be both one of the best and one of the worst? 

    Earlier this week I wrote about the best offseason moves in Phillies history and included the acquisition of Von Hayes. The Phillies acquired an All-Star caliber player who was better earlier in his career than Julio Franco, who was traded for him and would eventually become the better player. 

    But I am admittedly polarized on this one. 

    Any time you trade five players for a single man, there is a hefty expectation that you're acquiring along with the player. Hayes never developed into the superstar that the Phillies thought they were getting to take over post-Mike Schmidt, but the did get a solid player. 

    In the end, when you make a "five-for-one" type of deal, you need to come out on top. The Phillies probably didn't in the long run, but they made it close. Franco was the only notable player traded to Cleveland.

15. Jim Bunning

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    Acquiring Jim Bunning from the Detroit Tigers was easily one of the best moves in the history of the Phillies organization. The Tigers were selling low and it was the Phillies who pounced quickly to get a deal done. 

    A few seasons later, it was the Phillies turn to make a mistake with Bunning. Seeing that the team was going nowhere fast, they attempted to trade Bunning while his value was at its highest. He had just won 74 games for the Phillies in just four seasons. 

    It was a chance for the Phillies to land franchise changing talent, but instead, they found themselves swindled by the rival Pittsburgh Pirates

    The Pirates sent Don Money, Woodie Fryman, Bill Laxton and Harold Clem to the Phillies, none of whom had much of an impact. 

    Of course, it was assumed that this was another example of the Phillies' ownership group refusing to spend money on the team. Bunning was about to get expensive. 

14. Jonathan Papelbon

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    Jonathan Papelbon's contract is going to be a burden in the future whether or not he pitches well, but that's on Ruben Amaro Jr.'s shoulders. You can't blame a player for taking money when an executive is practically begging him to take it. 

    But that's the road ahead for the Phillies closer, who signed a four-year, $50 million contract before the 2012 season. According to FanGraphs, his performance was worth an estimated $6.3 million in 2012. 

    Simple math tells us that he'll have to be worth $43.7 million over the next three seasons to live up to that contract, and that doesn't even include the option year. 

    This contract was dead on arrival.

13. Geoff Jenkins

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    At the time, Geoff Jenkins seemed like a good addition for the Phillies, but not on a two-year deal. The outfielder was coming off of a season where he hit 21 home runs for the Milwaukee Brewers, but was in obvious decline. 

    The Phillies needed a right fielder, however. Following the loss of Aaron Rowand in free agency, Shane Victorino was the full-time center fielder and the Phillies had a new void to fill. 

    Jenkins would have been a solid stopgap, but he struggled big time, especially against left-handed pitching, and was eventually forced into a platoon with Jayson Werth before the latter took over full time. 

    The Phillies released Jenkins before the 2009 season began.

12. Jack Sanford

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    I didn't want to reach too far back into history for these transactions because the landscape of a baseball "offseason" has changed drastically, but this one is classic Phillies procedure. 

    In 1957, Jack Sanford won 19 games for the Phillies and was later named Rookie of the Year. Sounds like the start of a promising career, right? The Phillies saw it as an opportunity to cash in and sell high. 

    They sent him to the San Francisco Giants in exchange for a pair of players that never had much of an impact. Meanwhile, Sanford finished second in the voting for the Cy Young Award in 1962.

11. Raul Ibanez

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    Ruben Amaro Jr. drew the ire of people around the game once again before the 2009 season when he replaced incumbent left fielder Pat Burrell with former Seattle Mariner Raul Ibanez. 

    Pundits believed that Amaro had overpaid for Ibanez in terms of both years and salary, but through the first half of the first year of his contract, the outfielder made them looks silly. 

    It was all downhill from there. 

    Ibanez dealt with injuries over the course of the remainder of his contract. He played a sloppy left field and quickly became a near-automatic out against left-handed pitching. 

    The Phillies let him walk following the 2011 season and he signed with the New York Yankees on the cheap.

10. Gregg Jefferies

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    Normally, it isn't so hard to see the reasoning behind any given transaction, even if it winds up  being a terrible decision in hindsight. The Phillies signing Gregg Jefferies to a four-year deal still does not make sense to me to this day.

    First and foremost, this was a team in obvious decline. The Phillies had been to the World Series as a surprise team in 1993 and a year later, they were already fading away. 

    By 1995 only a facade of that '93 club remained. At this point, it should have been about rebuilding. Instead, the Phillies went and thew a ton of money at Jefferies on a deal that did not fit their situation. 

    By the fourth year, they had traded him to the Anaheim Angels

9. Placido Polanco

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    The Phillies have been drooling over the thought of acquiring a well-rounded third baseman since the day that they sent Scott Rolen to the St. Louis Cardinals in 2002, and they thought that they were going to get one in a familiar face. 

    The options at third base were thin prior to the 2010 season. Mark DeRosa and Adrian Beltre had durability concerns, so the Phillies decided to convince second baseman Placido Polanco to convert. 

    In order to do so, they had to guaranteed a 34-year-old second baseman three years to become a third baseman. The Phillies wound up getting one productive season out of Polanco before injuries derailed his career.

8. Dick Allen

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    Given the way the first few seasons of Richie Allen's career went, it was only fitting that trying to trade him would become a major headache for the Phillies. 

    Following the 1969 season, the Phillies had agreed to a deal with the St. Louis Cardinals that would land them Curt Flood, Joe Hoerner, Byron Browne and Tim McCarver for Allen, Cookie Rojas and Jerry Johnson. 

    The problem was that the Phillies were terrible at the time and Flood didn't want to play for them. He refused to report to his new team and the result was a long legal battle that resulted in the creation of free agency. 

    The Cardinals would instead send Willie Montanez and Jim Browning to the Phillies, the latter whom never appeared in an MLB game. They never received a similar level of talent to that of Allen. 

7. David Bell

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    How desperate were the Phillies to replace Scott Rolen? Desperate enough to sign David Bell to a four-year deal as a free agent. 

    Bell's first season with the Phillies was dreadful and marred by injuries. The following year represented a rebound while the last two were a gradual decline that eventually led to the Phillies dealing him to the Milwaukee Brewers. 

    After he had retired, Bell's name came up in a report that linked him to the use of steroids. 

6. Cliff Lee

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    I was going to put Cliff Lee on this slideshow twice, but I'll summarize why both of the deals involving the Phillies and their starting pitcher made during the offseason can be seen in a negative light. 

    The trade to the Seattle Mariners is the obvious one. With one, affordable year left on his contract, the Phillies would have been better off keeping Lee on the payroll. Instead, Ruben Amaro Jr. traded him to the Mariners for a light package of prospects that opened the criticism floodgates. 

    But the Phillies must have felt some remorse for pulling the trigger on that trade because they threw a boatload of money at him the following offseason. Was it the smart thing to do? 

    At the time, the Phillies already had their outlook of the future. Roy Halladay was earning $20 million per season and Cole Hamels was soon to follow. Did the team cripple itself with Lee's new mega-deal? 

    I don't think so, but it's worth thinking about. For the sake of this slideshow, focus on the trade.

5. Steve Carlton

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    This is the only example on this list of a deal not made coming back to haunt the Phillies, but then again, the way that the Phillies handled the back end of Steve Carlton's career was an absolute nightmare. 

    Carlton was still under contract with the Phillies during the 1986 season, but his career with the club was unraveling. He was already the greatest pitcher in franchise history, having won 241 games with the club and four Cy Young Awards. 

    But the Phillies were cheap. The haggling began and a media firestorm ensued. The Phillies wound up releasing Carlton in one of the most embarrassing moments in franchise history.

    It should also be noted that I cheated a little bit with this one. Carlton wasn't officially released until the month of June, but this was a transaction with months of build up that I thought could be included. Feel free to disagree, as always.

4. Willie Hernandez

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    Remember Willie Hernandez? I don't necessarily expect you to since the Phillies gave up on him pretty quickly. 

    Hernandez was a solid reliever who spent the bulk of his career in the 1980s. The Phillies had originally signed him as an amateur free agent, but the Chicago Cubs would later take him in the Rule 5 Draft—only to return him to the Phils. 

    So, they got another shot with Hernandez in the bullpen, and he was solid. He won eight games for the Phillies in 1983 as they made a run at the World Series. 

    In the offseason, the Phillies felt as though they had enough depth in the bullpen and had seen enough of Hernandez to move him. They traded him to the Detroit Tigers for Glenn Wilson and John Wockenfuss, neither of whom had an overwhelmingly significant impact on the Phils. 

    Meanwhile, Hernandez had a historically good season for the Tigers in 1984. When all was said and done that year, he was the American League MVP, Cy Young and a World Series champion.

3. Freddy Garcia

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    In typical Phillies fashion, they once tried to solve a starting pitching problem by trading away two quality starting pitchers for Freddy Garcia. 

    Okay, so that doesn't necessarily tell the entire story, but it is the truth. 

    Prior to the 2007 season, the Phillies needed some pitching. They had a lineup that could contend for the division, but the pitching staff was far behind. When the Chicago White Sox made the former All-Star Garcia available, the Phillies naturally listened. 

    Desperate for a legitimate front line starter, the Phillies sent former top prospect Gavin Floyd, whom they had all but given up on, and Gio Gonzales, who they had acquired from the White Sox in a previous deal, to Chicago for Garcia. 

    What a disaster. 

    Garcia pitched in all of 11 games for the Phillies and won just a single one. He left in free agency the following offseason.

2. Adam Eaton

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    If there is one name on this list that comes with an instant feeling of dread for Phillies fans, it has to be Adam Eaton. You can file this under that "Never Made Sense" category I talked about earlier. 

    Eaton was finishing up a stint with the Texas Rangers where he was realistically nothing more than mediocre, but the Phillies were desperate for a starting pitcher and thought that getting him out of hitter-friendly Texas would help. 

    It didn't. 

    They threw three-years and $24 million at Eaton and no one knew why. His stint in Philadelphia was horrible. Fans were so upset with his performance that they booed him as he received his World Series ring, and it was probably deserved. He didn't do much to get them there. 

    Naturally, Eaton was released before his contract expired.

1. Ivan De Jesus

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    After years of having Larry Bowa play shortstop, the Phillies were ready to move on. Bowa was fiery and confrontational and the Phillies were ready for a chance following their World Series victory in 1980. 

    One team that showed interest in Bowa was the Chicago Cubs. They were willing to swap their incumbent shortstop, Ivan De Jesus, with the Phillies—assuming that they would receive a prospect as a throw-in. 

    Well, they did. That throw-in would be Ryne Sandberg—future Hall of Fame second baseman. 

    Meanwhile, De Jesus played three mediocre seasons for the Phillies before moving on.