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The worst of Ruben Amaro Jr.

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Amaro is mostly remembered for bad things, even though his tenure was a mixture of both.

Bill Streicher-USA TODAY Sports

On Thursday, the Phillies fired general manager Ruben Amaro.

At the beginning of the season, this seemed like a forgone conclusion. The Phils were at the bottom of a cycle that took them from World Series champions to a team that would struggle to avoid losing 100. They were the laughing stock of baseball in the first half of 2015, and the product on the field looked bleak.

Fast forward to the end of August, and suddenly there was talk the Phillies might decide to keep Amaro. Although everyone knew Ruben wasn't calling the shots autonomously at this year's trade deadline, he was widely praised for getting a good haul in deals for Cole Hamels, Jonathan Papelbon, Chase Utley, Marlon Byrd and Jimmy Rollins over the last year. The farm system had been radically improved, and suddenly, the rebuild was looking a lot better.

But now, it's all over. And Amaro has left himself quite a legacy in Philadelphia.

And there are differing views on just what his legacy will be.

Amaro did some good things during his time at the helm, but he also did some bad things. And it's fair to wonder just how much of it, any or all of it, was solely the brainchild of Amaro or mandates given to him by team management, specifically former president David Montgomery.

Nevertheless, the dismissal of Amaro will be news of great joy for many. Even though he seemingly has been a more effective general manager over the last 24 months, his shortcomings on the analtytics side, numerous unwise public statements, and the desire of a new president to put his own man in the position, sealed his fate.

With that said, let's take a look back at the worst moves of Ruben Amaro's tenure as GM of the Philadelphia Phillies.

5. The Vesting Options

So many vesting options, those little poison pills at the end of deals that made dealing veteran players so difficult. They often caused confusion and delay, and made it harder for the team to begin the rebuilding process, simply because teams don't want to be on the hook for additional years and money. Yet, at the end of the day, the team was able to work around it and move every veteran on the team, with the exception of Carlos Ruiz and Ryan Howard.

But hopefully, the Amaro tenure has taught everyone to stay away from performance-based vesting options from here on out.

4. Phillies sign Jonathan Papelbon to a four-year, $50 million deal (with fifth-year vesting option).

For the record, Papelbon had an excellent career with the Phillies. He finished as the team's all-time saves leader and got better with each succeeding year. If it was possible for Papelbon to earn his salary, he did so. However, it wasn't possible, as Amaro dramatically overpaid for a closer, something almost no one does anymore, and needlessly soaked up payroll space that could have been used to improve other ares of the team in 2012 and 2013.

3. Phillies trade Jon Singleton, Jarred Cosart, Josh Zeid and Domingo Santana for Hunter Pence.

Honestly, this deal looked a lot worse last year, when all four of the prospects dealt to Houston made it to the Major Leagues. At the time of the deal, the Phillies were 50-30, on pace to win 100 games, and held a 4 1/2 game lead in the NL East. A spot in the playoffs was virtually guaranteed. And at the time, Domonic Brown, their hot prospect, was holding his own.

But the trade for Pence helped to scuttle Brown's development, all because of a perceived need for a "right-handed bat" in a lefty-heavy lineup. At the time, some believed Amaro made a master stroke in acquiring Pence without including Brown in the deal.

Not so much.

To be fair, none of the prospects deal by the Phils has turned out to be all that much so far. Singleton has played just 111 MLB games over the last two years and put up a slash line of .172/.289/.333 with 150 strikeouts in 415 plate appearances. Zeid has a 6.97 ERA as a reliever for Detroit this year. Cosart is a half-decent starter who has had a rough season this year, and Santana, despite immense power talent, is a walking strikeout waiting to happen.

What made matters worse was that the following season, the Phils sold low on Pence, despite having another year of team control, getting virtually nothing for him. Pence has since become one of the most valuable players in the National League.

2. Phillies sign Ryan Howard to five-year, $125 million contract extension.

There was no need to do this. After the 2009 season, Amaro added five years to the end of a deal that didn't finish until the end of the 2011 season. Howard was a premier power hitter at the time but had a profile that many believed would prevent him from maintaining that kind of production. More to the point, there was simply no need to sign him to an extension right then and there.

We all know what happened next. Howard ruptured his Achilles, and the four seasons since then have been an unmitigated disaster.

It should be noted that it's believed the Howard extension was done at the urging of Montgomery, so this may not have been a true Amaro blunder.

1. Phillies trade Cliff Lee to Mariners for Phillippe Aumont, Tyson Gillies and Juan Ramirez.

They could have had a Super Rotation in 2010. But after trading for Roy Halladay, the Phils felt they could no longer afford to also keep Cliff Lee, and on the same day as the Halladay deal, foolishly and hurriedly traded Lee for a series of high-risk prospects in the low minors of the Mariners system.

In their haste to jettison Lee, the Phils never really engaged all 29 other teams in a bidding war, and this was the result. Aumont was a disaster. Gillies was too. And I'm not even sure Juan Ramirez ever really existed.

These were the worst of the worst. The Raul Ibanez and Placido Polanco signings weren't great, but at least they were productive in their first seasons. Signing Michael Young and Delmon Young were dopey, but by that time things were already lost. And underrated bad moves were not planning properly for Howard and Utley's injuries in 2012, simply relying on Ty Wigginton and Michael Martinez to carry the load.

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