The 2021 Phillies will attempt to end the National League’s longest playoff drought after another off-season makeover

Nearly a decade has passed since the hideous evening at Citizens Bank Park that ended with Ryan Howard’s stumbling out of the batter’s box before eventually surrendering to the ruptured Achilles tendon in his left foot. Twenty feet away, Albert Pujols and his St. Louis Cardinals teammates celebrated the final out of their victory in the deciding game of the National League division series against the Phillies.

The Cardinals would celebrate twice more before the 2011 season was over as they captured their 11th World Series title with one of the great comeback stories in baseball history. The Cardinals have been to the postseason six more times since that magical run and are in the midst of 13 straight winning seasons.

The Phillies, on the other hand, have gone nine straight seasons without a playoff appearance or a winning record. The Cardinals, of course, are among the baseball elite with the second most World Series titles behind only the New York Yankees.

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Plenty of other teams, however, have also made postseason appearances since 2011. The Phillies, in fact, have the longest streak in the National League without sniffing the postseason. The only team in baseball that has gone longer without a playoff berth is the Seattle Mariners. The last time they were in the postseason was 2001, when some guy named Pat Gillick was their general manager and Jamie Moyer, at 38, was just reaching the prime of his career.

The Mariners have had three winning seasons since 2011, leaving the Phillies’ streak of nine straight years without a winning record as the longest in baseball.

“It’s just sort of shocking to go this long without getting into the playoffs, especially when you think about all the teams that got in last year,” said Larry Bowa, a Phillies senior adviser with an encyclopedic knowledge of the team’s history. “It’s not like the Phillies aren’t spending. I know [managing partner] John Middleton wants to win more than anybody and I’m really disappointed for him. He needs to be rewarded for what he’s done.”

Bowa, who spent all of spring training in uniform watching the 2021 team prepare for its second season under manager Joe Girardi, is optimistic about a season that will start Thursday against the Atlanta Braves at Citizens Bank Park. In fact, he even pulled a Jimmy Rollins, circa 2007, and predicted that the Phillies will win the National League East, although he did offer a disclaimer.

“I think our lineup from top to bottom is as good as any lineup in the National League East,” Bowa said. “We are going to score runs and I really like our three pitchers at the top. I like the two pitchers we picked up, too.”

The top of the rotation is Aaron Nola, Zack Wheeler, and Zach Eflin. The two new additions are veteran free-agent signees Matt Moore and Chase Anderson.

“Everything is aligned, so now the players have to go out and do it,” Bowa said. “Barring a major injury to someone like a [Bryce] Harper or Nola or Wheeler, I think this team is going to win the N.L. East. If they don’t win it, I’m going to be disappointed.”

Disappointment has resided at One Citizens Bank Way for quite some time and it’s disturbing to think a team that plays in the biggest single-team TV market in baseball has gone so long without winning.

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“When I saw that note go up the day I was hired about the Phillies going the longest span without being above .500, it caught me by surprise,” new team president Dave Dombrowski said. “I really think of the Phillies as a team with good players and a good foundation.”

During the nine-year playoff drought, the Phillies have had a top 10 payroll six times, including seventh a year ago. They project to be fifth in the payroll department in 2021 after re-signing top-tier free agents J.T. Realmuto and Didi Gregorius.

Despite Middleton’s willingness to spend, there are more than a few people who are not surprised by how long it has taken the Phillies to get back to the postseason.

“There was a stretch where we just weren’t very good and you have to be realistic about that,” Bowa said.

It was a stretch that started in 2013, when the team went 73-89, leading to Charlie Manuel’s removal as manager. Since then, three other managers (Ryne Sandberg, Pete Mackanin, and Gabe Kapler) have also been fired as have general managers Ruben Amaro Jr. and Matt Klentak.

“I’m a little surprised it has taken this long only because I thought we were on the right track when I was let go,” said Amaro, who is now working as a Phillies analyst for NBC Sports Philadelphia.

Amaro is not alone in that thinking.

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The Phillies’ farm system was ranked eighth by Baseball America ahead of Klentak’s first season as general manager, in 2016. The baseball trade magazine was super high on 2013 first-round pick J.P. Crawford, ranking the 20-year shortstop sixth among its top 100 prospects.

They also liked Amaro’s last trade, which sent Cole Hamels to Texas for five prospects, including outfielder Nick Williams and catcher Jorge Alfaro, both of whom were also considered top 100 prospects by Baseball America.

Like the Phillies, however, Baseball America was way off on outfielder Cornelius Randolph, a high school outfielder from Georgia who had been the 10th overall pick in the 2015 draft. That pick, which was the team’s first with Johnny Almaraz as the scouting director, proved to be debilitating for a team that needed help as soon as possible. Randolph, 23, is still in the Phillies system, but it appears unlikely that he will ever play in Philadelphia.

“I went and saw him and, to me, he looked like a young Tony Gwynn the way he hit the baseball,” Amaro said. “I saw him hit an opposite-field home run off a guy who was drafted in the second round the next year. It hasn’t worked out like we had hoped.”

Second-round pick Scott Kingery is the only player from the Phillies’ 2015 draft to reach the big leagues. The University of Arizona product quickly climbed through the minor leagues, buthe has not proven worthy of the six-year, $24-million deal the Klentak regime gave him before he had played a single game in the big leagues.

While the 2015 draft class has disappointed, the one before it, which was the final draft conducted by former scouting director Marti Wolever, has not.

Nola, the seventh overall pick in 2014, has been the best pitcher from that entire draft class and fifth-round pick Rhys Hoskins has hit the third-most home runs (91) from that class. Those two need to be primary contributors if the Phillies are to end their playoff drought this season.

The Amaro-era Phillies were criticized for waiting too long to start the rebuilding process. Looking back, however, it probably would not have made a major difference if the rebuilding had started right after the 2013 season instead of after the 2014 season.

By that point, most of the team’s stars (Howard, Chase Utley, and Roy Halladay) were fading because of injuries and had little trade value. The one exception was Cliff Lee, whose injury demise did not incur until the 2014 season. Still, Amaro acquired Eflin for Jimmy Rollins in December 2014 and that’s a trade that is still relevant for the Phillies five years after the three-time All-Star shortstop’s retirement.

The Hamels trade to Texas can still be linked to Realmuto’s arrival because Alfaro was part of that trade and Klentak used Crawford as part of the deal to acquire Jean Segura, who remains an integral part of this year’s team.

None of that changes the disappointment about the team’s excessively long playoff drought.

“I should take some blame that we didn’t turn this around faster,” Amaro said. “I believed in my heart of hearts that by 2018 we’d be close to where we wanted to be and we’d then be able to add some of the pieces we needed.”

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In truth, the Phillies, at least in their actions, emerged from rebuilding mode right around that time by signing Jake Arrieta to a three-year, $75 million contract. Arrieta was a free-agent disappointment, but some other things were also going awry, according to a baseball scout from an opposing team who agreed to speak only as an anonymous source.

“I really believe that after 2018 that club was heading in the right direction,” the source said. “There were players coming through the system and getting to the big leagues. Kingery got that extension because of the way he played in the minor leagues and he was legitimately good. Hoskins had come up the year before and did things that had never been done before and then he had another good season in 2018.

“But then Matt Klentak took the club down a road it did not need to go down in 2018 and 2019. What he wanted to do was way too drastic and way too quick and I think a lot of guys, with the exception of Nola, were negatively impacted. A lot of guys in the Phillies organization were marginalized who could have helped make better decisions.”

The baseball source said he believes Kingery and Hoskins were among those negatively impacted.

“They got away from being hitters,” the source said. “They tried to be power hitters the last couple years. Rhys Hoskins does not need to try to be a power hitter. If he’s a hitter, he is going to hit for power.”

As the Phillies became more heavily influenced by a growing analytics department, the baseball source said, Klentak stopped seeking input from some of the best minds in the organization, including Pat Gillick, the general manager of the 2008 World Series title team who now works as a team adviser.

“You look at the teams doing this right and they are using analytics and they are using, for lack of a better term, old-school baseball people,” the source said. “You use input from both sides and the Phillies got away from that. Matt stopped talking to people. He stopped talking to Pat Gillick. How arrogant do you have to be to not pick up the phone and seek advice from Pat Gillick?”

The source also pinned blame on Andy MacPhail, who after becoming the team president led the search that brought in Klentak as Amaro’s replacement.

“Andy always talked about how he hired people and then let them do their jobs,” the source said. “That’s what he did with Matt, but he should have been more hands on with what was happening.”

Another baseball source said Klentak and his top lieutenants — assistant general managers Ned Rice and Bryan Minniti — were not ready for the roles they assumed.

“None of them came from winning environments,” the source said. “And even Andy, he won with Minnesota, but that was a long time ago.”

MacPhail was the general manager when Minnesota won the World Series in 1987 and 1991, and the Chicago Cubs reached the NLCS with MacPhail as their team president in 2003. The Cubs, however, finished with a losing record in eight of his 12 years with the team and Baltimore had a losing record in each of his four full seasons as team president.

In Klentak’s previous eight seasons before being hired by the Phillies — four with Baltimore and four with the Los Angeles Angels — his teams made one playoff appearance. Rice was the Orioles’ assistant director of major league operations when the team made the playoffs in 2012 and 2014 and Minniti was an assistant GM to Mike Rizzo when Washington reached the postseason in 2012 and 2014.

Rice and Minniti remain in assistant general manager roles under Dombrowski and first-year general manager Sam Fuld while Klentak now works under the title of strategy and development officer.

Klentak declined to be interviewed for this story, but in fairness to him he was charged with the task of making the organization more analytically driven. At the time of his arrival, the Phillies were among the least analytically savvy organizations in baseball. A comparison between the 2015 and 2021 media guides reveals that Middleton’s mandate was more than accomplished by Klentak.

There was no mention of a research and development department in 2015. Now, the R&D department has 11 people and a variety of other front-office workers could also be tied to the team’s analytics process. Klentak, according to multiple sources, leaned much more heavily on the analytics people than his scouts.

While the Phillies failed to get back to the postseason under MacPhail and Klentak, their signatures remain on a huge portion of the ballclub. The bulk of the credit for the free-agent arrivals of Harper and Zack Wheeler belongs to the bank accounts of Middleton and the Buck cousins — Pete and Jim. But Klentak did deal for Realmuto and Segura, and the 2018 pick of Alec Bohm with the third overall selection looks terrific as the third baseman heads into his second season.

The jury, however, remains out on the first-round picks of Mickey Moniak in 2016 and Adam Haseley in 2017.

“I think one of the most concerning things about the team not making the playoffs for so long is the amount of money that has been spent,” former Phillies general manager Ed Wade said. “I think when you look at scouting and player development, the record kind of speaks for itself. The proof is in the fact that the club has been constructed mostly of seasoned players who were acquired by trade or in free agency.”

Wade built a Phillies team that came up short of reaching the postseason, but he left Gillick with a strong foundation and a farm system that gave the Phillies the maneuverability needed to finish the product and win a World Series in 2008.

“The goal is to get good and to stay good, and that’s usually achieved through solid scouting followed by consistent player development,” Wade said. “Even the larger payroll clubs have been able to draft, sign, and develop core players and solid complimentary pieces.”

The first step must be a return to the playoffs and the consensus seems to be that Middleton, on his second try, got things right with his persistent pursuit of Dombrowski.

“I think Dave’s hiring was huge for what they are trying to accomplish,” Wade said. “He has proven he can win and he has proven he can win quickly. If he doesn’t already have Hall of Fame credentials, he is working toward them. I don’t think they could have done any better than David.”

Time will tell if that is enough to end a playoff drought that is nearly a decade long. If it does, it’s possible Klentak’s work as general manager will be more fondly remembered than it is right now.