Oddly, it is the present that is far more difficult to predict for these five. Their situation is rare and even unheard of since the turn of the century because they work in a profession besieged by turnover.
How rare is it that five guys who came up through a team's farm system would still be together six years after they won the World Series? You won't find another team in the 21st century that has done it. This, of course, is looked upon as more of a curse than a blessing by fans who have grown weary of general manager Ruben Amaro Jr.'s attempt to squeeze one more magical season out of an aging core.
Considering the rapid descent the team has been on the last two seasons, it's an understandable fan reaction. But it's also not unreasonable for Amaro to believe that he can win with guys who have won before. It's not just young teams that win or reach the World Series.
Half of the 26 teams that have played in the Fall Classic since the start of the 21st century have had position players who averaged more than 30 years of age. The list includes last year's World Series champions, the Boston Red Sox.
The Phillies' projected lineup for this season has an average age of 31.5. The 2009 team that went to the World Series had an average age of 31. Four World Series teams in this century - the 2001 Arizona Diamondbacks (33.9), the 2001 New York Yankees (31.7), the 2002 San Francisco Giants (33), and the 2004 St. Louis Cardinals (31.8) - had regulars who averaged more than 31.5 years of age.
Eleven of the 26 teams that have played in the World Series since 2000 had starting rotations that averaged more than 30 years of age, and, again, that list includes the team that won the World Series a year ago. The average age of the Phillies rotation this season will be 32 when Hamels returns from the disabled list. Only the 2000 and 2003 Yankees (33.4 and 34.2, respectively) and the 2004 and 2007 Red Sox (32.8 and 32, respectively) reached the World Series with rotations that were older or the same average age.
If anything, it appears as if Amaro has modeled his recipe for success on the way the Yankees and Red Sox have done things. Each team is not afraid to take on players with advanced years, and the Yankees, in particular, kept their core around longer than most teams that reach the World Series.
That likely has a lot to do with the fact that they have been able to afford to do so, which is the same position the Phillies and Red Sox have been in.
The Yankees team that won the World Series in 2009 still had four players - Derek Jeter, Jorge Posada, Andy Pettitte, and Mariano Rivera - from the team that had won in 2000. They were all older than the core five who remain for the Phillies, but they still were key contributors to the Yankees' last World Series run.
That's not to say that this Phillies team is on the brink of something spectacular. Recent returns indicate that the only special moments that remain for the core five will come when they are inducted into the Wall of Fame.
One by one and sometimes maybe even two or three at a time, they are going to disappear from the ballpark they made rock for so many years.
Rollins, 35, appears likely to be the first to go because he has the least amount of time left on his contract and his burning desire to finish his career in Philadelphia could subside if the 2014 season bears any resemblance to the previous two.
Howard, 34, has reached a crossroads in his career because of injuries. If he can't avoid the disabled list for an extended period of time this season, the Phillies might have to eat his enormous contract, live with the financial indigestion, and move on to a better solution. That's what teams with a lot of money are able to do.
Utley's knees did not betray him last season, but he is 35 and there is no guarantee they will hold up again. He had a difficult spring and even though his contract extension says it runs through 2018, the only guaranteed money runs out next season.
Ruiz, 35, is signed for three more seasons and he might just end up outlasting the rest of the core position players, which would have seemed highly unlikely when we watched the 2008 World Series celebration.
Hamels, 30, is signed through 2018, but pitchers can be fragile, as we saw this spring when he arrived in camp with biceps tendinitis. Elite pitchers can also bring great value in trades, and it's possible Hamels could be used in that fashion long before his contract expires.
It's unheard of in this century that five core players from the farm system would still be together six years after they won the World Series, but that's how the Phillies general manager has chosen to go about his business. Amaro believes it's a winning formula. If he's wrong, more of the core and maybe even the general manager will disappear.