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Is it harder to get to the top or stay at the top? Hall of Fame GM Pat Gillick will probably tell you it’s harder to stay at the top. While he still serves as an advisor to the Phillies, Gillick left the hot seat to Ruben Amaro Jr. right after the 2008 World Series parade.

To his credit, Amaro has acted boldly in keeping the Phillies at the top of the NL East if not at the top of Major League Baseball when the postseason rolls around. He brought in Cliff Lee in 2009, Roy Halladay in 2010 (and after subtracting Lee, brought in Roy Oswalt), brought Lee back in 2011 and made the shrewd exchange of letting Jayson Werth go and bringing in the lower cost Hunter Pence, pocketing 2 compensatory draft picks for good measure.

Of course, nearly each of these moves cost the Phillies pieces from their farm system. Mortgaging the future always comes with a price to be paid down the line.

Ironically, though, it’s not really the dwindling number of well-regarded farm players that is hurting the Phillies. No one they’ve traded away has even remotely resembled Ryne Sandberg. The three guys sent to the Indians for Lee – Carlos Carrasco, Jason Donald and Lou Marson – are marginal at best. Kyle Drabek (Halladay trade) is recovering from Tommy John surgery and hadn’t pitched consistently well in the majors before he got hurt. Anthony Gose (Oswalt trade) had a career batting average of .265 in the minor leagues – and in his brief major league callup this season, hit .091, though he is only 21 years old. The jury is still out on Jarred Cosart and Jonathan Singleton (the key pieces in the Pence deal).

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The bigger problem for the Phillies is too much money tied up in too few players, some of whom are in noticeable decline, and which also leaves little money for middle relief, left field or third base – areas which have undone much of the good work of the core players. It doesn’t help matters that Amaro and his staff guessed wrong on whom to choose with the limited resources they had for these areas.

Sure it would help if John Mayberry progressed from his breakout 2011 instead of regressed. It would help if Domonic Brown – whom Amaro tenaciously steered other teams away from while he was dealing other prospects – progressed at all.

But the “damned if you do, damned if you don’t” nature of Amaro’s strategy centers around keeping the core players here. It’s good for the fans to keep being able to watch Ryan Howard ($105 million due for next 4 years or $118 million due for next 5 years, at which point Howard will be 37 years old) and Jimmy Rollins (most likely $33 million due over next 3 years, at which point Rollins will be 36 years old) continue to be Phillies. Same with Chase Utley (a relative bargain at $15 million for one more season…or will it be less than a full season? Utley will turn 34 this offseason). But ask anyone around baseball, and those guys aren’t earning their keep and probably won’t ever again. Cliff Lee’s 3 years remaining at $87.5 million or 4 years at $102.5 million is suddenly looking like a bitter pill (Lee turns 38 in the 4th year). Add Jonathan Papelbon‘s record-setting contract for a closer (with 3 more guaranteed years and $39 million due, with a vesting option for a 4th year at another $13 million, at which point Papelbon is 35) , and the Phillies are even more top-heavy. Roy Halladay and Carlos Ruiz are free agents after 2013 – and it’s not clear that the Phillies will be able to retain them.

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Of course the spotlight for now is on Cole Hamels, to a lesser degree Shane Victorino, and to an even lesser degree, Joe Blanton and Placido Polanco – all of whom are free agents after this season.

Polanco is hurting the team now with his constant ground ball outs, and his .255 batting average – a far cry from his career .300 mark. He won’t be back. He also has minimal trade value.

Blanton looked like he was being overpaid at $8.5 million for 2012, but he’s second on the Phillies’ staff in wins (with 8) and may have some trade value now, despite leading the league in both hits allowed (137) and home runs allowed (22).

Victorino was discussed in my last Phillies Notebook. He is underachieving and has no ideal place in the batting order. He also has some trade value. Or instead, the Phillies could try to get a “sandwich” pick for him between the first and second rounds of the June 2013 draft – but they’d have to offer him a one-year deal at about $12.5 million to qualify for compensation, and Victorino might accept, since it would be a $3 million raise for him. That would be another player arguably in decline who is getting paid above his level of production.

Despite all this, it’s Cole Hamels who is the keystone to the Phillies’ future. Amaro seems to recognize this and has apparently offered Hamels a 6-year contract extension worth $127 million. The Phillies may go as far as $135 million, which would be an average of $22.5 million per season, which is the same amount that the Giants’ Matt Cain got earlier this season, on a 5-year extension. Six years and $135 million is also the full value of Cliff Lee’s current contract, if the sixth year vests.

But Hamels very well may not sign. At least not before he gets the chance to see who else is interested and what else they are offering once he becomes a free agent in November. Hamels has already indicated recently that he’s looking forward to finding out what he’s worth. But he’s also said in spring training that the Phillies are the only organization he’s played for and he considers that a good thing in terms of the fan support and the winning.

But will the winning continue after what we’ve seen in 2012? It’s not like getting Utley and Howard back has changed much in terms of the results on the field. The weaknesses on this team are dragging it down faster than the strengths of this team are propping it up.

Hamels must see that and be concerned, even if he hasn’t articulated it publicly.

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It’s not like the Phillies aren’t committed to winning from a total dollars spent standpoint – their payroll is tops in the National League and trails only the Yankees and Red Sox. They are very close to the luxury tax threshold, and may exceed it in 2013 (when it remains at $178 million). Most teams are scrambling to be under the luxury tax threshold in 2014 – which is expected to climb to $189 million but also will carry stiffer penalties for exceeding it.

It’s just that the paradox of winning with younger guys brings about huge raises for those guys both at the peak of their popularity with fans and the peak of their production as players. There is often nowhere to go but down.

Nobody begrudges the players the opportunity to earn big money when they are eligible for free agency – but the concept that there is a ‘home team discount’ once a player approaches or reaches free agency is absurd. The true home team discount takes place in the first 2-3 years of major league service time, when the team pretty much writes down a number on the contract/paycheck and the player has to accept it. For the next 3-4 years, there is inflation of compensation, but the degree of inflation is tied to performance because salary arbitration (or the threat of arbitration) brings the players’ compensation more in line with their performance, but still well below the type of dollars and commitment in years that the full-fledged bidding war of free agency creates.

I understand that everyone agreed to this system, but if you give it a long hard look, it makes it impossible to align the continuity of star players with winning (just ask the Cardinals about the joy of winning a World Series only to watch Albert Pujols leave town about a month later). Only players who break into the big leagues at 21 years old or younger (like Bryce Harper at 19) are truly at the peak of their careers when they get to free agency (most have pegged 27 as a major leaguer’s prime age). Most top free agents are around 29 or 30 years old (Hamels turns 29 this off-season, Victorino and Blanton each turn 32). Add in the fact that most free agent contracts for good players are in the 3-4 year range and for great players are in the 5-10 year range, and you see that the deck is stacked against the teams who “win” the opportunity to bid crazy money to obtain or retain their services, since on average, the players are several years past their prime when they sign and possibly a decade or so past their prime when the team is finally done paying.

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Not that I’m advocating hiring Billy “Moneyball” Beane as the Phillies’ GM and changing players faster than underwear.

But to ridicule Jayson Werth last year for not only taking big money but also heading to the Nationals, a team that has picked at or near the top of the amateur draft for a bunch of years now, was totally foolish of Phillies fans. Players can talk about a team demonstrating a “commitment to winning” by spending money, but a savvy player knows that a team with 4 or 5 key players no older than 27 (such as Harper, Stephen Strasburg, Jordan Zimmermann, Ryan Zimmerman and Ian Desmond) is a much more likely winner over the long haul than a team which owns 4 or 5 $20+ million per year players who are all in their 30′s.

Get ready for a “new world order” in the National League.

And wouldn’t it hurt not only for the Phillies to be “sellers,” but also to watch them “sell” Shane Victorino to the Pirates?

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