Ruben Amaro Jr. has seen this before.

A few times, actually.

In 2003, the Phillies led the wild-card race by a half-game before losing seven of their last eight and missing the playoffs for the ninth year in a row. In 2006, they went into the final week with a half-game lead but finished 3-4 and extended the postseason drought to 12 years.

It wasn’t until 2007 that the Phillies finally kicked down the door to October, and it wouldn’t have happened then either if not for a 13-4 finishing kick and a Big Apple-size collapse by the New York Mets.

The point is, it’s not easy to close the deal, especially for a team that hasn’t done it before. Winning, like hitting a breaking ball, must be learned. And after wilting down the stretch in 2018 and 2019, the Phillies are still in class, perilously close to an ignominious three-peat entering the season’s fateful weekend.

“I think there’s real, tangible -- I don’t know how you measure it -- experience in big-game situations that really means something,” said Amaro, the former Phillies general manager. “Going through it, having the feel of what it takes to play when the game is on the line, when your season’s on the line, I think it’s a critical part of the growth of an organization and the growth of a player.”

In that case, the Phillies are still growing.

They haven’t been to the playoffs since 2011. Nobody is left from that team. Of the 28 players on the active roster, only nine have appeared in a postseason game; six have advanced beyond the first round; two -- injured starter Jake Arrieta and struggling reliever Brandon Workman -- own a World Series ring.

There’s something to be said for those experiences, which Bryce Harper -- 0-4 in series with the Washington Nationals -- describes as “the funnest environments I’ve played in.” But completing the journey is equally invaluable.

“Winning baseball is something I think you need to learn,” said Phillies manager Joe Girardi, a four-time World Series champion. “It’s learning how to control everything around you -- your surroundings, your emotions in big situations, being prepared all the time for a situation that might come up, being able to discipline yourself when you are beat up and tired. I do believe you have to learn all of that.”

It should begin in the minor leagues, Girardi says. Although the emphasis there is rightly on player development, he noted the value of experiencing a pennant race down on the farm, where winning can become part of a player’s DNA.

The Phillies were cognizant of that as they rebuilt. Andrew Knapp, Roman Quinn, and Zach Eflin went to the Eastern League finals in 2015 with double-A Reading. Rhys Hoskins, Scott Kingery, and Quinn made the playoffs with Reading in 2016. Spencer Howard threw a postseason no-hitter at low-A Lakewood in 2018 and joined Alec Bohm and Mickey Moniak in the postseason with Reading last year.

Bryce Harper says he came to the Phillies to win a World Series, but he has yet to play for a team that has won a playoff series.
YONG KIM / Staff Photographer
Bryce Harper says he came to the Phillies to win a World Series, but he has yet to play for a team that has won a playoff series.

But there’s nothing quite like a big-league playoff push. In a sport that stresses keeping an even keel, the stretch drive is a nightly roller coaster, with emotions varying as wildly as playoff odds with every win and loss.

Amaro points to the mid-2000s Phillies. After collapsing in 2003, they finished six games out of the wild card in 2004, one game back in 2005, and three games short in 2006. By 2007, many folks doubted they would ever get over the mountain.

“But we were playing important games,” Amaro said. “In ’05 we got close. In ’06 we got close. In ’07 we got in the playoffs and guys learned. It was like, ‘OK, I know what this is like now.’ All that stuff is really valuable.”

From a distance, then, Amaro wondered in 2018 if the Phillies did a disservice to Kingery and other young players by reducing their playing time after acquiring veterans Asdrubal Cabrera and Jose Bautista for an unexpected playoff run.

Even many of the Phillies' best players -- notably catcher J.T. Realmuto, co-aces Aaron Nola and Zack Wheeler, and infielder Jean Segura -- haven’t successfully navigated a playoff race.

“Man, I’m waiting for that moment,” Segura said recently. “I’d love to be in the playoffs and having a playoff game because I never did it in my career. I think it’s time to go there.”

The Phillies were solidly positioned with a 20-17 record, fifth-best in the National League, on Labor Day. Since then, deluged by injuries to Realmuto, Hoskins, Arrieta, Howard, and others, they are 8-12, slipping a half-game behind Miami for second place in the NL East (the Marlins own the tiebreaker), one game behind San Francisco and Cincinnati for the wild-card spots.

Manager Joe Girardi is trying to get the Phillies into the playoffs for the first time since 2011.
Nick Wass / AP
Manager Joe Girardi is trying to get the Phillies into the playoffs for the first time since 2011.

It’s fair to question whether the Phillies deserve October baseball, even with a postseason field that has expanded to include eight teams, more than half the league. But it’s undeniable that they would benefit -- personally and organizationally -- from the experience.

“There’s a lot of guys, a lot of really good players that never make the postseason,” Harper said. "It’s very special when you get there. But you’ve got to want it. You’ve got to be able to come in here every single day and want to battle no matter how you’re feeling, no matter the emotion you feel, your physical being. You have to come in here and want it every single day.

“I think it would solidify us in many different ways. Being able to get free agents to come here because they know we’re a postseason team that they can come to and help us win. That’s why I came here. I came here to get the Philadelphia Phillies back to Broad Street. That’s what I want to do. I think that’s what the players in that clubhouse want to do. And that’s what we have to do as an organization and as a team right now.”

Doing it, of course, is the hard part.