Top 10 Gut-Wrenching Losses in Philadelphia Phillies History By: Hank Indictor

The Philadelphia Phillies have been in existence for well over a century. Many great players have come and gone while gracing the Red Pinstripes; however, despite this, the Phillies have the dubious record for most losses in their franchise history. Though they've won 2 World Series Championships, the team has also suffered numerous episodes of heartbreak. After all, despite being established before cars were invented, the Phillies have only reached the playoffs 16 times! They've had multiple playoff droughts that have lasted a decade and some for over 20 years. Anyway, after their most recent debacle in the 2023 NLCS (more on that later), I felt compelled to count down the most gut-wrenching of all the losses in Phillies history, which might seem hard given all the years they've been in existence until you remember most of these occurred during the playoffs and those losses were memorable for all the wrong reasons. Remember, it took until their 97th year of existence to win one World Series, so it's hard to believe that the Phillies were never glorified with a "curse" like the Red Sox and Cubs. Let this be a trigger warning for those Phillies fans reading this. These losses that will be discussed will all have taken place during the modern era, as in the 1960's and beyond. The reason for this is that other than their losses in the 1915 and 1950 World Series, the Phillies, for the most part in the first half of their existence, stunk out loud due to a combination of poor team construction, racism, and terrible ownership. Also, even in those World Series appearances, the Phillies didn't have losses that you'd consider "gut-wrenching," at least compared to what happened later in the modern era. I also am excluding the 1976 NLCS because that Phillies team got swept by a historically great team in "The Big Red Machine." And one other pattern you'll see with this list is the residual long-term effect they had on the team. Without further ado, let's get to the list!

10. The Secretary of Defense Loses the Series in the Sun:  1978 marked the Phillies 3rd consecutive trip to the NLCS, and for the 2nd year in a row, they played the Los Angeles Dodgers. After dropping the first two games at home and facing elimination, the Phillies would rebound in Game 3 thanks to a complete game by "Lefty" Steve Carlton, who would also help his cause by hitting a home run in that game. In the 4th game, the Phillies forced their way to extra innings when Bake McBride's clutch home run tied the game in the 7th inning. And in the bottom of the 10th, it looked like the game would go into extra innings when Tug McGraw retired the first 2 batters he faced but after walking Ron Cey he would then face future manager Dusty Baker, who would hit a flyball to Garry Maddox, who inexplicably lost the ball in the sun! To make matters worse, the next batter would hit a line drive single to Maddox, who tried to throw the ball home but booted it before he had the chance as he allowed the winning run to score. This was not only gut-wrenching in that it was a walkoff loss to end the series (this, my friends, is what we call foreshadowing), but Garry Maddox was one of the greatest defensive center fielders in baseball history, the "Secretary of Defense" was on his way to 8 consecutive Gold Gloves making those blunders all the more shocking. In addition, this was the Phillies 3rd consecutive loss in the NLCS. Still, I can't put this series higher than 10th because not only did the Phillies nearly get swept here, but the game was tied when Maddox botched consecutive plays, so who knows if the Phillies even survived this game had he at least caught the first fly ball. And even if they had won, they still would've had to play a Game 5 in a dicey situation because Lefty had already pitched Game 3, but that's neither here nor there. Fortunately, they would win their first-ever World Series and eliminate the "choker" label two years later. Therefore, this loss was a blessing in disguise based on the butterfly effect, as it led to them signing Pete Rose and the firing of Danny Ozark in favor of Dallas Green. Still, you can't argue it wasn't gut-wrenching at the time.

9. Ivan deOops:  The first true good stretch in Phillies history was from 1976-1983, and little did people know that this World Series run marked the end of an era. Granted, this team was still different from the one that had won in 1980; after all, they had lost guys such as Greg Luzinski, Bob Boone, and Larry Bowa, to name a few, and the remaining members were showing their age (although Mike Schmidt was still his prime). Their team had the oldest average age in the league at 34 years old. Included in the mix were 39-year-old Steve Carlton and 42-year-old Pete Rose, and before the season, they had added 2 of Rose's Big Red Machine Teammates and future HOFers, Joe Morgan and Tony Perez (40 and 41 years old respectively. As a result, the team was known as the "Wheeze Kids" (the Whiz Kids was what the young 1950 team was known as). Despite the big names, the team struggled through the first half, and G.M. Paul Owens fired Pat Corrales and made himself the team's manager. This would lead to a solid 2nd half by the Phillies as they broke away with the division, but after consecutive playoff defeats, they would finally beat the Dodgers in the NLCS to set up a World Series with the Orioles. After splitting the first two games in Baltimore, the Phillies looked good as the series moved to Veterans Stadium. They carried a 2-1 lead into the 7th inning, with Steve Carlton having pitched a strong game. Unfortunately for them, this was when the wheels came off. After getting two quick outs, the Orioles would tie the game on a double by Benny Ayala, and then when Ivan deJesus booted a ground ball hit by Dan Ford, the O's took the lead and would go on to win the game. Even though the next game would also be close, the Orioles' momentum in this one was the difference in this series, and they would win the 5th game pretty easily. However, I also have this at a low ranking because, again, Baltimore was the better team in this World Series, and as I said, the Phillies were nearing the end. Unfortunately for them, it would be an entire decade before they would even reach the playoffs again, much less the series, but more on that one later. Also, here's a not-so-fun fact: Ivan deJesus came to Philadelphia in the trade that sent Ryne Sandberg and Larry Bowa to the Cubs. 

8. Inability to Slay Juan Uribe and the Giants: After losing the World Series to the Yankees the previous year, the Phillies bolstered their pitching staff by trading for "Doc" Roy Halladay, who not only threw a perfect game in the regular season but threw a no-hitter during their NLDS sweep of the Cincinnati Reds as well! They were headed for their 3rd straight World Series, which would likely put them in the dynasty discussion. However, this was the series in which they ran into a San Francisco Giants squad that, on paper, didn't look like they had any business beating the Phillies, or at least if you compared their lineups and factored in experience, so what happened? In Game 1, Cody Ross turned into Barry Bonds by hitting a pair of home runs off Doc, and they were the difference in their victory. Although the Phillies would bounce back in Game 2, Matt Cain would shut them down as the series shifted to the Bay Area. But in reality, the Phillies lost this series twice. The first time was in Game 4, where they not only blew a 4-2 lead but, in a tie game in the 9th inning, Charlie Manuel shockingly used his #2 starter Roy Oswalt to send this game into extras. That move backfired spectacularly; Oswalt had nothing, and Juan Uribe walked it off with a sacrifice fly. Despite this, the Phillies would send the series back to Philly in Game 5, but in the 6th game, the Phillies offense would go completely A-WOL after taking a 2-0 lead and being unable to capitalize on a wild Jonathan Sanchez. On the other hand, the Giants would rally and win the game with a home run by Juan Uribe, and then Brian Wilson got out of trouble in the 9th when he struck out Ryan Howard looking. While not entirely on the gut-wrenching level as some of their other losses, the 2010 NLCS was a missed opportunity for the Phillies. Granted, the Giants had a phenomenal pitching staff. Still, their lineup featured guys like Ross, Uribe, Freddy Sanchez, Edgar Renteria, and even former Phillie Pat Burrell, Not quite Murderer's Row. Aubrey Huff also led the team with 24 home runs and 86 RBIs. They had Rookie of the Year, Buster Posey, but he wasn't yet a star. Therefore, despite a pitching staff that featured a still in his prime, Cain and Tim Lincecum remember that the MadBum who started Game 4 was only 21 years old and not yet a legend. This was one of the series that elevated some of the Giants to that status! In contrast to the Phillies lineup, the better team lost this series. Still, even with this missed chance at glory, this wouldn't be their worst loss by a long shot.  

7. Damon's Mad Dash: Coming off their 2nd World Championship, the Phillies would return to the Fall Classic in 2009, hoping to repeat against a powerful New York Yankees squad. And looking back at this World Series, it was closer to being a Phillies repeat than what many may remember. In fact, as a Yankees fan, I appreciate this one more and more with time after so many subsequent near misses, but that's neither here nor there. It looked like the Phillies were in good shape when Cliff Lee made like a buzz saw in Game 1. And even though the Yankees would even the series in the Bronx, they still had to go through the raucous Citizens Bank Park. However, despite the Yankees winning game three after trailing 3-0 early, it was the 4th game that was the actual turning point that won the series for the Yankees and ended any hopes of a Philadelphia repeat. Trailing 4-3 in the 8th inning, Pedro Feliz hit a game-tying solo home run, and with Lidge getting the first two outs, it looked like the game would go to extras. But when Johnny Damon hit a single to keep the game alive, he would not only steal 2nd but alertly take 3rd since nobody was covering the base due to the overshift. He would then score when A-Rod drove him in with a single, and the Yankees would get some insurance runs on a two-run single by Jorge Posada. The win was necessary for the Yankees because it not only meant they had three chances to win the Championship, but a loss to Cliff Lee in Game 5 didn't hurt their chances. However, Hideki Matsui's home run would put a nail in the coffin and give the Yankees their 27th Championship. Would a Phillies repeat have us look at the 2007-2011 run differently? Most likely, after all, they'd probably be in the discussion among the greatest teams, but despite the crazy turn of events in Game 4, the Yankees were a strong team and likely would've won Game 7 anyway, even if Pedro had pitched better in Game 6. Still, we'll never know.

6. Topper makes the Wheels Fall Off: Let's fast forward to the next Phillies World Series appearance in 2022. At the time of Joe Girardi's firing, it looked like the Phillies' playoff drought would continue as they were seven games below .500. From there, the Phillies would turn things around under interim Manager Rob Thomson, and despite a 3rd place finish in the NL East, they would reach the playoffs for the first time since 2011 thanks to the new playoff format. From there, the Phillies would go on a shocking run to the World Series, facing the juggernaut Houston Astros. But in Game 6, with the Phillies trailing 3 games to 2, came a controversial decision by Rob Thomson (more foreshadowing). Kyle Schwarber would hit a solo home run to put the Phillies up 1-0 in the 6th inning, but the bottom half was when trouble started. Phillies ace Zack Wheeler hit leadoff batter Martin Maldonado, and though he would rebound by getting an out, Jeremy Pena would get a single to make things dicey. Rather than allow his ace to attempt to get out of trouble, Topper removed Wheeler from the game in favor of Jose Alvarado. Noted clutch hitter Yordan Alvarez would hit a 3-run home run that would essentially salt away the World Series for the Astros. Maybe Wheeler would have given up a big hit to Alvarez, too, but then again, the Phillies only scored one run in that game, and since the combined no-hitter in Game 4 struggled to score runs the rest of the way. However, Dusty Baker's track record in Game 7s begs the question: What if the Wheeler got out of trouble and the Phillies won Game 6? Still, given the recent events, I'm sure the fanbase would do anything to get back to this game.

5. Chico Ruiz sets off the infamous "Phold": The Phillies have had several late-season near misses and pennant race losses. The Septembers of 2003 and 2005 generally come to mind. However, none of them were nearly as bad as the losses mentioned on this list, and none were on the level of 1964. This is arguably the Worst Collapse in all of Major League Baseball history. Had just one game during the infamous 10-game losing streak gone differently in September of 1964, this Phillies team would probably be celebrated, and the losing culture might have changed sooner. However, it was not meant to be. This was a team that shocked many as they came out of nowhere during the summer of 1964, spending much of the season in first place, and were up by as many as 9 and 10 games. The season's highlights came when Hall of Famer Jim Bunning threw his famous Father's Day Perfect Game, and star outfielder Johnny Callison hit a walk-off home run to win the All-Star Game for the National League. But as the team made it halfway towards September, their "Phold" was just as shocking as their rise to first place. The Phillies would lose 10 in a row, with 7 of those games coming in their final homestand. The first game of the streak, however, was the most devastating. In a scoreless game in the 6th inning, Frank Robinson was at bat with Chico Ruiz on 3rd. Phillies pitcher Art Mahaffey had no reason even to check 3rd base, especially since the batter was a future Hall of Famer and their most significant threat to bring in Ruiz. But inexplicably, Ruiz took off for home despite protests from his 3rd Base Coach! Mahaffey was caught off guard so badly that he threw the ball wildly, allowing Ruiz to score easily. This would be the only run of the game for the Reds, and from there, it seemed as if there was panic. During much of the losing streak, Phillies manager Gene Mauch started his best pitchers, Jim Bunning and Chris Short, several times on short rest (sometimes with as little as two days!). Some notable losses in the streak included a 12-inning heartbreaker to the Milwaukee Braves and a game in which Johnny Callison hit three home runs only for the Phillies to lose 14-8. The nail in the coffin came when the Pennant-winning Cardinals swept the Phils, and even though they won the last two games of the season in Cincinnati, it wasn't enough to prevent what was arguably the greatest collapse in postseason history. Now, why is this only #5? After all, finishing first until 1969 automatically meant a World Series appearance. Well, I say this because we'll never truly know if the Phillies would've beaten the Yankees in the World Series. Although the Cardinals would end up doing so, it still took them seven games, some of which could've gone either way. And if we look at the rosters, it's not all that big of a shock that the Cardinals would win the pennant. Still having read books about this team and Dick "Richie" Allen, I often wonder how much that collapse truly affected how his career played out in Philly. After all, despite being a below-average fielder and prone to strikeouts, he was establishing himself as a true star and would go on to have big seasons. But due to controversy in and out of his control (some of it about race as Allen was the first black star in Phillies history), he became an enigma by the end of the '60s. He belongs in the Hall, but that's a story for another day. Nevertheless, it's a real shame that this particular team couldn't finish off the Cardinals. Who knows how they would be remembered had they won just one more game? And maybe Manager Gene Mauch also ends up in the Hall of Fame

4. Black Friday: This one and the subsequent loss I will mention are pretty much interchangeable. However, you can argue that the 1977 Phillies were statistically the best team in franchise history. That's not to say their NLCS opponent, the Dodgers, was a joke, far from it. After all, this squad was one of the biggest powerhouses then. But if there's one game in that series that symbolizes the fortunes of the Phillies for much of their existence, it would be Game 3. After splitting the first few games at Dodgers Stadium, a win here would be vital, with Steve Carlton slated to pitch Game 4. The Phillies were up 5-3 in the 9th as Gene Garber retired the first two batters. But then, without warning, Vic Davalillo laid down a bunt single. Then Manny Mota hit a fly ball that would be misplayed by Greg Luzinski, who should have been out of the game as Jerry Martin, the defensive replacement, was still on the bench, not only allowing Davalillo to score but Mota went to third on the Bull's errant throw to 3rd. Davey Lopes would then hit a ground ball that bounced off of Schmidt's glove and into the hands of Larry Bowa, whose throw to first appeared to be on time. But Umpire Bruce Froemming called him safe, tying the game, and the Phillies would subsequently give up the go-ahead run. Even with Carlton on the mound, the Phillies would never recover as they lost the rain-soaked 4th game. Ultimately, we'll never know if this team could've beaten that legendary Yankees team in an alternate universe, but the idea of them facing off against each other is quite intriguing. This could've led to a dynasty, especially given what happened in 1980, for all we know. But as I've proven. The Phillies are a team of "what ifs."

3. No runs for the Doc means Insult to Injury: Why am I putting the 2011 debacle ahead of 1977? Unlike in the '77 series against the Dodgers, the Phillies had a chance to finish off the Cardinals not once but TWICE! And in each game, they failed. But getting eliminated in front of your home fans in Game 5 makes it much worse. Especially when the Final score is 1-0, in this game, the Phillies could only muster three hits off of Chris Carpenter, and in the 9th inning, the image of Ryan Howard will remain haunted in the minds of Phillies fans forever. However, this was the ultimate missed opportunity. This was worse than losing to the Giants was for them in 2010. Remember, this was the Cardinals team that only made the playoffs, with the Braves choking away a Wild Card Spot. This Phillies team had most of the same core intact from the previous few years (J-Roll, Ryan Howard, and Chase Utley, to name a few). This was a pitching staff loaded with Aces such as Halladay, Hamels, and Oswalt. Whether or not they were better than the '77 team is debatable, but the competition ahead of them was very beatable. And I'll never understand why Ruben Amaro Jr. didn't blow things up right then and there, as it was apparent that this was their last chance for a follow-up for 2008. It took an entire decade for them to return to the playoffs. Yet somehow, the most recent debacle was a worse one. Much worse!

2. Snakes on a Plane: Sure, putting the 2023 NLCS this high on the list is a case of recency bias. And you'd be right. But since the AL and NLCS were expanded to a seven-game series in 1985, there haven't been many series that can be considered a monumental collapse. Nothing will top 2004, of course, because reverse sweeps are even rarer than perfect games. But this collapse for the Phillies is about as bad as it gets. After two convincing wins in front of the home crowd, this series should've been over. Maybe they found snakes on a plane? I don't know. But what is known is that the Phillies left a village of men in scoring position as the series shifted to the desert. Losing Game 3 and only scoring one run that day was no big deal. You knew Arizona wouldn't go down quietly. But with a 5-3 lead in Game 4 going into the 8th inning, it seemed like they had the game won. And the real question is this. WHY ON EARTH ARE YOU USING CRAIG KIMBREL?!?!?! It's common knowledge that if he pitches for your team, you should receive a warning from the surgeon general. And what does he do? He gave up a game-tying home run to Alek Thomas and then continued to get hit before Jose Alvarado allowed his inherited runner to score on a single by Gabriel Moreno. But no big deal, you say Zack Wheeler won the next day, and the Phillies need one home win, and they're golden. But they couldn't even do that! And to make matters worse, their biggest bats in the two home games (Schwarber, Turner, Harper, and Castellanos) got a combined total of 1 HIT!!!! This was arguably their best chance at winning a title in a long time, and they pissed it away big time. But there's still one loss I have yet to cover for them.

1. Joe Carter tames the Wild Thing: I don't care that the '93 team was a one-year wonder and lightning in a bottle. Giving up a walk-off home run to lose a World Series is as rough as it gets. Sure, we'll never know if the Phillies would've won Game 7 had Joe Carter not hit that home run off of Mitch "Wild Thing" Williams, but there was also Game 4, which was their chance to tie it and put a scare into the Jays. In the 8th inning of an offensive explosion, they were up 14-9, but neither Larry Andersen nor the Wild Thing could hold on to that lead giving the Phils a 15-14 loss. In other words, the Phillies lost this World Series twice! To this day, that "wacky wonderful bunch of throwbacks" remains beloved in Philadelphia. They may have been juicing, but they were a group of every man. Ones that looked more like a beer league softball team than major leaguers, and sure, they may have been wild, but that's what so many loved about this squad. And since they fell apart and declined just as quickly as they shocked the world (it took them 14 years to reach the playoffs again), you could make a case that it makes the Carter home run just as devastating. Still, even though Toronto was the better team, this type of World Series loss is brutal. And for a franchise that's suffered many losses in its well over a century-old existence, it's by far the most gut-wrenching of them all!