In his 42 years in baseball, Branch Rickey helped rebuild three franchises, with all three surging from also-ran status to champions either during or soon after Rickey’s tenure. Win that often and people start to hang on your every word — which is how Rickey gained a reputation as one of the most quotable figures the game has ever known. One of his most commonly repeated nuggets of wisdom remains a model for many GMs today: “Trade a player a year too early rather than a year too late.”

It’s easy to see the merits of that idea. Trade a player at the height of his value and you can set your team up for years to come with what you get back; wait too long and you’ve got a player who’ll do less to help your team, whether you keep him or shop him. More broadly, Rickey’s message stressed the importance of avoiding having teams that were too old. You can win with the same core for a while. But eventually, the superstars and fan favorites of the past become the overrated players of the present and the overpaid albatrosses of the future.

It’s also easy to get carried away with contempt for aging players and aging teams. In many cases, older teams are also very good teams. They’ve re-signed their best players rather than let them test the open market and signed premium free agents to help keep multiyear winning streaks going. If you’re a big-revenue team trying to stay on top for an extra year or two, running out older, more established players can add more predictability to your performance and lower the chances of wild swings and big disappointments that up-and-coming prospects can and do often provide. Put simply, age often implies, and predicts, success.

Unfortunately, that model can’t work forever. Ride the same players too deep into their 30s and you’ll inevitably see injuries and big drops in performance, the kind that can crush any team, even those that might have rolled through October a year earlier. The question then becomes one of choice. Do you try to squeeze one more year out of your teetering veterans? Or do you start an aggressive reloading process, trading past-prime, big-name players for young talent who can help in the relatively near future?

This is the dilemma the Phillies face heading into the 2013 season. They’ve already turned over more than half the lineup, handing starting roles to much younger players. But none of those players are premium prospects. Moreover, the team’s trio of infield stars, the ones who’ve been the face of Phillies baseball for nearly a decade, are still around, fighting injuries and Father Time as they desperately try to keep the Phillies relevant in a division that’s left them behind. Then you’ve got the starting rotation’s three aces and the fire-breathing closer, all making big bucks, all hugely attractive gets for many other teams were they to become available. Four months from now, if Philly appears on its way to another mediocre season, should the team cash in their biggest trade chips for younger players who could help build a winning team for 2014 and beyond?

Maybe the bigger question is this: If the Phillies do reach that point, could they go through with it — tearing down the most dominant collection of players the team has seen in 30-plus years?

It’s become something of a sport for analysts, and some fans, to go after Phillies GM Ruben Amaro Jr.; you won’t find a more cleverly derisive name in all of baseball than “Ruin Tomorrow Jr.” But there’s a long list of factors conspiring against successful teams to maintain that success, even when they have huge financial resources at their disposal.

It starts with low draft position. Win five division titles in a row and you’re certainly not lamenting drafting 27th and 28th every year, at least not in the moment. Developing a top prospect into a major league–ready player can take a while, too, especially if that prospect came out of the high school ranks. But at some point, you’ll look up at what you’ve got in the high minors and, barring a run of supernaturally good later-round draft picks, find that the cupboard’s pretty bare.

As a team’s success continues, the urge to sacrifice the future in favor of the present only intensifies. Need to sign a big free agent to shore up your bullpen? That’ll cost you a potentially valuable draft pick. Need to plug your leaky outfield at the trade deadline? It might cost you multiple high-ceiling prospects to do it. Punting long-term upside in favor of win-now commodities like college closers in the draft? That happens. Offer way too much money to a star and fan favorite, long before such a decision even needs to made? That happens, too. We can squawk all we want about building a great farm system or earning praise by making inspired and unorthodox moves. A general manager’s job is to win the World Series. If and when he gets there, his job is to keep it up. Everything else is, and should be, secondary.

The challenge becomes how to do it. Rany Jazayerli covered the Phillies’ shaky future back in 2011, as the team was on its way to a 102-60 record, the best in franchise history. Despite that success, Jazayerli called out the very large, very old elephant in the room:

Philadelphia’s hitters are getting old all at once. In 2007, when this batch of Phillies first made the playoffs, the average age of the offense was 28.8 years old. Three years later, the average age of the Phillies’ offense was exactly three years older. At 31.8 years old, the 2010 Phillies had one of the 10 oldest lineups in NL history. This year, their hitters are just a tick younger — 31.5. Only a handful of teams in history have fielded an offense this old in back-to-back seasons, and almost all of them paid a price.

He then listed a bunch of teams with similarly old rosters and what happened once those veterans started to fade. The 1984-86 Angels, 1997-2000 Orioles, 2001-02 Diamondbacks, and 2003-04 Mariners in particular experienced brutal declines following their trips to Geezerville, with the resulting carnage taking years to repair. Add to that list the Tigers after 1987-89, who took nearly two decades to make it back to the playoffs, and the Padres after 1996-98, who went from a World Series berth to five consecutive sub-.500 seasons in last or second-to-last place. The common thread for most of these teams was a flailing attempt to laissez les bon temps rouler, in which teams a year or two removed from the height of their glory tried to double down on win-now moves rather than accept their fate and make moves that could help down the road. The ’97 Orioles won 98 games, the front office kept plowing money into free agents, and the team didn’t have another winning season for 15 years. The Diamondbacks waited a little long to trade aging stars like Randy Johnson and Curt Schilling, getting decent but still underwhelming returns. The Mariners spent half a decade trying to recapture their early-aughts success before finally pillaging their farm system to get Erik Bedard, a move that still haunts the club five years later.

The Mariners’ case in particular was a classic example of what can happen when a general manager’s interests aren’t directly aligned with those of the team he’s running. We can concede that winning a World Series is the ultimate goal. We can acknowledge that when a GM trades prospects who might not make the big leagues until after he’s fired for a player who can help right now, his intentions aren’t necessarily nefarious. But trading Adam Jones, Chris Tillman, and three other players for Bedard was both a failure to read the true talent of a roster and a case in which someone should have been there to slap a reality check on the situation.

The best-case scenario for any team is to have everyone pulling in the same direction — from the owner down to the team president, GM, manager, coaches, and players. So if a trade that looks good at the time that it’s made goes wrong for tough-to-foresee reasons, or a manager makes unconventional moves that piss off the media (e.g., leverage-based closer usage), no one gets fired.

The most effective rebuilding models may well require that level of cooperation to work out best for all involved. Everyone, even small-to-medium-revenue teams like Seattle, Cincinnati, Tampa Bay, and Pittsburgh, is locking up their best players before they can reach free agency, making it increasingly difficult for older teams to plug holes that way, no matter how much money they might have to burn.

So maybe a rebuilding plan like Boston’s, in which the Sox jettisoned more than a quarter-billion dollars in salaries, signed a few midlevel free agents to keep the team respectable and keep revenue sources from falling off a cliff, and made sure not to offer a bunch of six-year deals that might’ve blocked the path for the wave of exciting prospects coming up, is the way to go. Or maybe the Astros have the answer, gutting their house down to the foundation in a flurry of deals, building entirely from within (for now), and being honest with their fans all along, with the hope that when the team does become good again, attendance and TV ratings will rebound accordingly. It’s risky business no matter how you do it. Get too aggressive with your teardown plan and it can take years for fans and revenue streams to come back, even well after the team has started winning again. Hell, there’s an argument to be made that no team should rebuild, ever.

So what does Amaro do if this year looks a lot more like 2012 than 2011, as expected?

The most obvious trade candidate is Roy Halladay. The future Hall of Famer saw his fastball velocity dip and his performance suffer as a lat strain limited him to 156 innings, his lowest total in seven years. Halladay still posted a 3.69 FIP and 3.60 xFIP, suggesting that he retains ample value even in a down year. If his health and velocity return this year (he’s looked fine so far in spring training), Halladay becomes a valuable trade-deadline commodity in the final season of his three-year contract. Cliff Lee has three years and $87.5 million (including his 2016 buyout) left on his deal and is coming off a season that wasn’t anywhere near as bad as his 6-9 record would suggest, but was still his worst in five years by advanced metrics. Still, if the Phillies paid part of his freight, Lee too could help restock the farm system or deliver the kind of pre-arbitration players who could become important pieces of Philly’s next winning team. Chase Utley’s not the player he once was, but still represents an upgrade over many teams’ current second-base situations if his knees can hold up in the walk year of his own deal. Ditto for Jimmy Rollins and the two years and $22 million he’s still owed.

Of course this is all much easier on paper than it’ll be in real life. Amaro’s almost certainly more optimistic than the rest of the world about his team’s chances, banking on not only the veterans but also on new, younger additions to the lineup like Darin Ruf, Ben Revere, and Domonic Brown. It’s possible that ownership wants no part of rebuilding, not with fans flocking to the ballpark and the afterglow of NL East dominance still in effect. Ryan Howard’s launching majestic homers again this spring. The Phillies even have the National League’s second-easiest early-season schedule, which could lead to a hot start and a stronger urge to add to what the team has, rather than subtract.

The most likely scenario probably involves a path somewhere in between blowing it all up and doing nothing at all. If Utley can’t stay healthy again this year, the Phillies can just let him walk next winter and look for a younger replacement. There’s a good chance Rollins won’t be back after 2014, no matter what the rest of the team looks like. Carrying Halladay, Lee, and Cole Hamels for the next few years isn’t likely to happen, and we should probably expect one of the three to be gone by next spring, whether by trade or with Halladay pursuing free-agent dreams somewhere else.

Just don’t count on those half-measures bearing fruit anytime soon. The Phillies own one of baseball’s worst farm systems, with their best talent likely three or four years away and none of those players anything close to a sure thing. They owe $104.5 million to just six players for 2014, and four of those six (Howard, Rollins, Jonathan Papelbon, and Mike Adams) might be no better than two-win players by that point. And the Nationals have built a team that has the rare combination of youth and elite talent, the kind that makes you wonder if the rest of the division could be fighting for wild-card scraps.

It might not take another 28 years for Philadelphia to host a parade. But it could be a while no matter what becomes of Ryan Howard, Chase Utley, Jimmy Rollins, and the rest of this once-unbeatable team.