Smashing success and Philadelphia Phillies’ baseball are two phrases that haven’t been uttered in the same sentence very often over the 131 year history of the franchise. No professional sports team has suffered more defeats and few teams have tasted glory less often than the boys in Philadelphia. By the time the Phillies moved out of Veteran’s Stadium one magical, Steve Carlton-fueled run in 1980 was all that stood between the Phillies and an 0-for-the-century.

But with the move to shiny, new Citizens Bank Park in 2004 came a shiny, new ball club. In 2005 the team hired Charlie Manuel, who has been the most successful manager in franchise history, and gave the full-time 1st base job to Ryan Howard, who would go onto win the Rookie of the Year Award and then an MVP.  2006 saw the arrival of Cole Hamels, a future World Series MVP who fit nicely alongside a deep, talented offense chalked full of All-Stars. By 2007 the franchise had captured their first division title in 14 years, which would set off a run of 5 straight NL East crowns. And then in 2008 they finally hit pay dirt, capturing a World Series title in 5 games over the Tampa Bay Rays.

The following seasons would only bring more success and more big names. Cliff Lee was brought in via trade, then swapped out for ace Roy Halladay, then brought back in via free agency. Roy Oswalt would join the staff to create a new Phab Four and a slew of productive veteran outfielders, including Raul Ibanez, would find a way to make an impact in the lineup. But none of those moves yielded another crown and after a franchise-record 102 wins in 2011, the Phillies have bottomed out again with a record of 50-58 this season.

So the real question is, how did we get here? How did the Phillies go from a National League dynasty and 5 straight NL East crowns to a franchise struggling to stay afloat? And is it possible that if GM Ruben Amaro Jr. navigated another course, things would have turned out for the better? Let’s take a look at some of the moves that put sand in the Phillies’ engine.

– The Extension

Like many franchises around the Major Leagues, Philadelphia decided it would be a fantastic idea to pay their power hitting 1st baseman, Ryan Howard, an exorbitant amount of money. And, like many of those same franchises around the league, that massive 5 year/$125 million dollar extension has blown up in their face. Now, to be fair, part of Howard’s problems stem from his inability to stay on the field thanks to a horrific achilles injury suffered at the conclusion of the 2011 NLDS. But even before Howard’s achilles imploded, there were some not so subtle warning signs that inking the lefty to a big deal was a mistake.

Just check out Ryan Howard’s career splits:

Against righties: .295/.390/.606 (.996 OPS), 234 HR, 688 RBI, 1 homer every 14.37 plate appearances

Against lefties: .224/.300/.428 (.728 OPS), 77 HR, 275, RBI, 1 homer every 21.48 plate appearances

That’s a massive, massive split in production folks and it’s one that has essentially reduced Ryan Howard to the role of “a very expensive platoon player” as Ruben Amaro Jr. put it. And the issues don’t stop there either. Pitchers absolutely refuse to throw Howard a fastball as they opt to feed him a steady diet of breaking pitches and he’s flailing. The Phillies’ 1st baseman is hitting just .221 against anything that isn’t a fastball and he’s struck out 47% of the time in his 122 plate appearances against off-speed and breaking pitches. There isn’t an offensive in the game today that can survive that kind of lack of production in the middle of the order.

– Never pay for a closer

There’s an old maxim in fantasy baseball that says you should never, ever pay for saves. Competent closers are a dime a dozen with new 9th inning stars being born every year. Just take a look around the league and you’ll see a dozen new closers who have been perfectly satisfactory at shutting the door. So when the Phillies decided to pony up $50 million dollars for 4 years of Jonathan Paplebon’s services before the 2012 season the general reaction among baseball scholars wasn’t very kind.

There was cause for concern over the Phillies lack of remaining finances. There was also concern that Philadelphia and Amaro Jr. had overspent on their pitching staff, which would leave the offense high and dry, especially if Howard wasn’t able to return to his pre-injury form. There was also concern that someone as volatile as Paplebon wouldn’t exactly fit in a rough and tumble place like Philadelphia.

Well, for the most part those concerns were extremely well-founded. Paplebon has done a solid job at the end of the Philadelphia bullpen, posting a 2.38 ERA in his two seasons with the ball club. Unfortunately a top-notch closer is only useful to a team in the thick of the pennant race and, as Paplebon himself said, “I definitely didn’t come here for this.” Coupled with Howard’s $25 million dollar abomination, the Phillies have $38 million to a 1 inning specialist and a platoon hitter. Neither of those moves can be found in the GM’s handbook on how to run a successful team and combined, those two players are effectively crippling the Phillies’ maneuvering abilities.

– Where’s the base running? Where’s the walks? What happened to the Phillies’ way?

Throughout their incredible 5 year run atop the NL East, if you turned on a Phillies’ game you were guaranteed to see an aggressive, entertaining style of play, particularly on the base paths.

Just take a look at where the Phillies ranked in base running value during their run according to Fangraphs:

2007: 16 runs above average (1st in baseball)

2008: 17.8 runs above average (1st)

2009: 11.8 runs above average (5th)

2010: 5.5 runs above average (8th)

2011: -0.8 runs above average (16th)

2012: 3.7 runs above average (12th)

2013: -4.2 runs above average (20th)

A similar things happens if you take a look at the Phillies’ walk rates over the years as well. During their run from 2007-2011, Philadelphia never once ranked lower than 11th in walks and they placed in the top 10 in 4 of the 5 seasons. That’s quite a difference from this current lineup, which currently sits 28th in baseball in walk rate. That’s an extra runner or two a game taken off the base paths and thanks to some age-related decline, Philadelphia just can’t afford that drop-off.

– Know when to hold ’em and when to fold ’em

Perhaps the biggest criticism being directed toward GM Ruben Amaro Jr. right now is that he doesn’t have a good understanding of what his team actually is.

Philadelphia currently sits 13.5 games back in the NL East and they’re 9.5 games back of the 2nd Wild Card spot. That’s not a manageable deficit for a team that ranks 13th in the NL in runs scored and dead last in the league in runs allowed. That’s the sort of profile you usually see accompanying 100 loss teams looking to sell, not ones with designs on chasing a pennant.

So if we establish the fact that the Phillies aren’t really contenders, than we should also be able to come to the conclusion that they should do everything in their power to improve for the future. That means trading away useful veterans on shorter contracts. It means pursuing prospects, calling up players from Triple-A, and working toward 2014.

But that’s not what Amaro Jr. is doing. Instead, he held all his cards at the trade deadline and, from the looks of things, he only paid lip service to the idea of selling of his veteran pieces. This is the oldest roster in the National Legaue. At what point does management decide to push for a younger team? What, exactly, do the Phillies have to gain from another two months of Chase Utley? How is Michael Young going to help the ball club win a championship when his contract’s up at the end of the year?

The market for productive players was barren and the Phillies could have made out nicely. Instead they chose to delay the rebuilding process by another year by holding out hope that this team can get healthy and get it together. News flash Ruben. That’s not going to happen.

Philadelphia’s’ dynasty is dead. Complacency, age, and poor contracts killed it.

Big thanks to Baseball-Reference, Fangraphs, and Brooks Baseball for the statistical help!