In a franchise full of difficult nights, it’s harder to find a more somber image in Phillies history than Ryan Howard crumbling to the turf 10 years ago this month as the season ended. The Phillies won 102 games that season, but the Four Aces could not win a postseason series. And it ended with Howard, his Achilles tendon ruptured, being helped off the field.

As gutting as that night was, it was impossible to know how impactful it would be. It was the immediate end to one of the greatest eras in team history as the group that took the Phillies to five consecutive postseasons would never be the same.

Those Phillies — Howard and Jimmy Rollins and Chase Utley and Cole Hamels and Roy Halladay and Cliff Lee — made rally towels an October tradition in South Philly. But ever since that night, playoff baseball has eluded the Phillies. For the 10th straight year, baseball’s postseason will not include them.

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As painful as it was, it still didn’t feel like it would take more than a decade for the playoffs to return to Philadelphia.

“It’s crazy, man. Time flies,” Howard said last week before watching the Phillies play in Atlanta. “Organizations go through these types of things. Growing pains. A lot of different things and people that came in and out of the front office and all that kind of stuff. Now that you’ve had that kind of change over again, it’s people trying to get the folks that they want in and get their spoon into the pot and mix it up.

“Once you get a new front office regime coming in, you’re kind of dealt the hand that you’re dealt and you have to play with that hand and start making adjustments from there.”

Team president Dave Dombrowski is the third person to oversee the Phillies’ baseball operations since that night. He replaced Matt Klentak, who replaced Ruben Amaro Jr. Dombrowski inherited a fractured farm system that was slim on prospects and struggled to move players in a common direction.

Dombrowski committed roughly $160 million last winter to free agents and acquired pitching help at the trade deadline, but the lack of a productive minor-league system remains the biggest hurdle to October. The Phillies were able to play 44 postseason games during a five-year stretch because they first built a healthy farm system.

That was supposed to be the plan when they traded Rollins before the 2015 season to trigger a rebuilding process. But seasons of low payroll and low wins have failed to churn out homegrown talent.

Of the Phillies’ 10 leading players in 2021 by WAR, just one — Odúbel Herrera, chosen in the 2015 Rule 5 draft by Amaro — was drafted during the rebuilding years. And just one — Zach Eflin, who was acquired by Amaro — came via a rebuilding trade.

Zack Wheeler, Bryce Harper, and Andrew McCutchen were premium free agents. Jean Segura and J.T. Realmuto were brought in by Klentak in return for packages headlined by players acquired by Amaro, who drafted Rhys Hoskins and Aaron Nola and signed Ranger Suárez before the rebuild began.

» READ MORE: Phillies’ offseason to-do list: Help Bryce Harper, upgrade infield and go deep on pitching

‘Lifeline’ in minors

The Phillies have not been shy about spending money the past four winters, but they’ve failed to surround those free agents with the homegrown players they intended to draft and develop during a rebuild that averaged 95.3 losses per season from 2015-17. And that’s why the rebuilding process, which was mostly overseen by Klentak’s regime, has failed to reach October.

“Your minor leagues have to be a feeder. It has to be a lifeline,” manager Joe Girardi said. “I always call the minor leagues a lifeline because when you need someone to come up and replace someone, they’re there. Or if somebody goes down for three weeks, that piece is there for you to do it. You can’t just go out and sign every free agent. You just can’t do it. As much as we would love to and John Middleton is extremely generous, he just couldn’t afford it.”

Dombrowski, less than a year after joining the Phillies, overhauled the minor leagues this summer and will ask Preston Mattingly to “make sure everybody is on the same page and understands what that page is” as the new farm director.

The Phillies believe the minor-league system shifted too far into analytics and new-age instruction and away from traditional methods. It will be Mattingly’s job to balance that, but the bulk of the Phillies’ prospects are in the lower levels of the minor leagues and it could take time for him to produce.

“It’s challenging,” general manager Sam Fuld said of finding a balance between old and new. “On paper, you recognize the importance of executing a plan like that, but it can be a little bit more challenging in practice. That’s why we focused on what we focused on and why we’re excited about Preston as an individual and him having the ability to connect and empathize with others who have different backgrounds and thought processes and where they’re coming from. Including a diverse set of thoughts is a really important part of this job.”

Holes to fill

Dombrowski enters the offseason with holes to fill. The Phillies need to determine whom their shortstop and third baseman will be along with left and center field. They need help again in the bullpen and the starting rotation.

This is when a productive farm system would have helped. Instead, the Phillies likely will address most of those holes without outside additions.

» READ MORE: Phillies fire hitting coach Joe Dillon, infield coach Juan Castro before season finale

It’s going to take heavy lifting for the Phillies to enter 2022 as postseason contenders. The Braves aren’t going anywhere and the Mets are reportedly trying to land a superstar to run their baseball operations department to pair with the game’s richest owner.

But this will be Dombrowski’s first full offseason leading the Phillies. He’s spent nearly a year evaluating and this winter could give us a feel for what he has seen. If the trade deadline was an indication, he’ll be aggressive. He didn’t blink when trading the pitching prospect whom the previous regime had deemed untouchable (Spencer Howard).

If the Phillies finally break their postseason drought next October, it’s going to take a creative winter.

“It’s trending in the right direction, it’s just a matter of getting over the hump,” Ryan Howard said. “... It’s just one of those things where it has to be a bad taste in your mouth. Ultimately, you get to the point of saying ‘I’m tired of not making it’ and ultimately you just decide that you’re going to make it.

» READ MORE: Joe Girardi says Phillies still see Alec Bohm as a third baseman

“Barring injuries and stuff you can’t control like that, but you can have a group where if you don’t make it, you look out and say next year or in the offseason or when you get to spring training, ‘Yo, we’re not having what happened last year, happen this year.’ I think that’s what the difference was with our groups when we played.

“It was ‘Why not us? We know what we’re capable of doing and we know who we are.’ It’s just a matter of that for these guys, finding out who they are as a team and who they want to be as a team. Once you decide like, ‘Hey man, we’re going to go out and win this thing,’ then you can go do it.”