The Philadelphia Phillies have the distinct honor of suffering the most losses in American professional sports. Ready for the number? That would be 11,366. They have lost 365 games more than the next closest team, the Braves. Only the Padres have a worse franchise winning percentage than the Phillies (.474). To really put this into perspective, the Phils would have to win their next 1,105 games just to get back to .500. That would be nearly seven consecutive seasons of going 162-0.

So, for a franchise that has been around since 1883, it’s safe to say there are quite a few moments to ponder, “What If?”

Here are 142 years of hypotheticals and the Top 10 “What If?” moments in Phillies history.

10. What If… the Phillies traded for Randy Johnson in 1993?

The Phils lost 92 games in ’92. Entering the season, nobody gave them a Phightin’ chance. Mitch Williams even joked the expansion Marlins were predicted to finish ahead the Phils in the NL East.

But something unexpected happened. Something that can’t be measured in slash lines or fielding percentages. The Phil found magic. They found each other, fell in love and became a contender. Ultimately, it ended in Game 6 in Toronto with Joe Carter in Game, 6 but might be there have been one man who could have altered that World Series? 

After the ’92 season, the Mariners and Johnson were far apart on a contract extension and started fielding offers. So how close were the Phillies to actually landing the Big Unit? 

Depends on which rumor mill. Some speculate the trade would have had to include Schilling in a swap of aces. That makes little sense for the Phillies. In that scenario, Johnson just replaces Schilling’s 1993, who was elite in the ’93 playoffs. They’re very likely in a similar situation.

On the other hand, if it was Ben Rivera, Tyler Green or Mike Lieberthal holding up the deal, like former Phillies’ first baseman and current TV color analyst, John Kruk, has alluded to, the Phillies make this move, stack Johnson and Schilling 8 years before the Arizona Diamondbacks do, and go into the 1993 Postseason with a nasty 1-2 punch.

How does this impact the Phillies? Randy Johnson was 19-8 with a 3.24 ERA with 308 strikeouts in ’93, finishing second in the AL Cy Young voting to 22-game-winner Jack McDowell. The impact is obvious in the regular season, but it’s even more important in the postseason. The Phillies’ bullpen was taxed by the time they got to the World Series against the Toronto Blue Jays. Johnson takes some burden off the bullpen. He also allows the Phillies to send Terry Mulholland to the mound one less time in the World Series, where he gave up eight earned runs in 10.2 innings pitched.

Randy Johnson goes on to pitch at least twice in the 1993 World Series, pairing up with Schilling for four starts, just as they did in the 2001 World Series for Arizona. Is it enough to push the Phillies past the Toronto Blue Jays? It certainly would have been an infusion of life for a pitching staff that was running on fumes by the end.

9. What If… the Kansas City Royals selected Mike Schmidt in the 1971 MLB Draft?

In the spring of 1971, the Royals and Phillies had consecutive selections at No. 5 and 6 in the MLB Draft. The players who were selected with the fifth and sixth overall picks in the 1971 MLB Draft will forever be connected because… well, their names were Roy. That’s about it. While both Roys were busts, the second round proved entirely different.

With the 29th pick, the Royals selected third baseman (shortstop, at the time) George Brett. The Phillies selected Mike Schmidt with the following pick. The two produced Hall of Fame careers and are in the conversation for best third baseman of all time. But what would have happened if the Royals took Schmidt instead of Brett?

Well first, let’s compare numbers.

Mike Schmidt: 2404 games played. .267/.380/.527/.908 548 HR 1595 RBI 3X MVP 10X Gold Glove winner 6X Silver Slugger winner.

George Brett:2707 games played. .305/.369/.487/.857 317 HR 1596 RBI 1X MVP 1X Gold Glove winner 3X Silver Slugger winner.

As you can see, Schmidt’s career numerically was more accomplished in the homerun category, which led to a higher OPS. Schmidt led the NL in homeruns eight times, hitting 30 or more 13 times in 14 seasons. Brett hit 30 homeruns in a season just once. But Brett finished his career with over 900 more hits and 200 more doubles. Brett hit over .300 eleven times in his career. Schmidt accomplished that just once. They were two different hitters who found enormous success.

The great differentiator could be the glove. Brett was fine enough defender. Schmidt is referenced as one of the best defensive third baseman of all time. The sheer number of Gold Gloves back it up.

The pair were each other’s contemporary, unmatched by most, if not all, over their careers. Both spent their entire careers with the teams that drafted them. Both are Hall of Famers. Neither was the wrong choice. But, if you ask me to make an unbiased selection, the Phillies ended up winning this one. If the Royals take Schmidt, its very plausible they win the 1976, 1977, 1978 and 1980 Division titles, just like they did. And there is a chance the two meet in the 1980 World Series, as well. This is a rare instance where both teams come out winners in the most unpredictable Draft.

8. What If… J.D. Drew signs with the Phillies in 1997?

J.D. Drew, a name uttered in disgust in Philadelphia sports lure, will forever be tied to the Phillies. Drew was selected by the Phillies with the 2nd overall pick in the 1997 MLB Draft. Drew made it abundantly clear he had no interest in signing with the Phillies unless they seriously upped their contract offer. The Phillies had no plans of doing so. So Drew didn’t sign, and went to play Independent ball instead. He re-declared for the 1998 Draft and was selected by the St. Louis Cardinals with the 5th overall pick.

But what would have happened if the Phillies, Drew and agent, Scott Boras, would have come to terms on a deal before the 1997 season?

It’s actually a really weird scenario that would not exist in today’s game. There’s a chance that the Phillies could have had J.D. Drew AND Pat Burrell. From 1965, when the Kansas City Athletics selected Rick Monday, through 2005, MLB had an “alternating leagues” rule in the amateur draft. The rule indicated that, every other year, the worst team in either the AL or NL would make the first overall pick, alternating years.

The Phillies weren’t the worst team in baseball in 1997, but they were the worst team in the National League, posting a 68-94 record. The Oakland A’s and Kansas City Royals each had worst records than the Phillies. But, because it was the National League’s “turn” at the number one overall pick, the selection was awarded to the Phillies. With the understanding that a signed J.D. Drew would almost assuredly not be on the big league club, the Phillies still would have posted that 68 win season. So with the first overall pick in the 1998 MLB Draft, the Phillies still select Miami’s Pat Burrell.

The Phillies would have had two Major League ready hitters in their organization. Drew made his debut in 1998 for the St. Louis Cardinals. He played just 14 games. He started the 1999 season with the Cardinals. Burrell, meanwhile, made his big league debut in 2000 with the Phillies. There is a scenario where Burrell and Drew are on the Phillies 2000 roster together. Burrell played 111 games in 2000, 58 at first base, 48 in left field and four as a DH. The Phillies could have used Drew in left field and allowed Burrell to grow as a Major League first baseman, already having Bobby Abreu in right field.

The ripple effect asks if the Phillies still want Travis Lee in the Curt Schilling deal? Would they have preferred a different position player, or perhaps another arm in return?

The alternative timeline suggest the Phillies don’t take Burrell number one overall, but instead, opt for Mark Mulder, who went second to the A’s. Mulder would have enormously helped the Phillies rotation in the early 2000’s, including in 2001, when the Phillies won 86 games, despite having four starters make 15 or more starts and post 4.16 ERAs or worse.

There is a very real scenario in which the Phillies outfield/first base features BOTH J.D. Drew and Pat Burrell.

7. What If… Jerry Martin replaced Greg Luzinski in the 1977 NLCS

The year is 1977. The Phillies had just made the Playoffs for the first time in 26 seasons the year prior, but were swept out in 3 games. They entered ’77 a different team. Not in terms of roster, per se, but in terms of mentality. They tasted the Playoffs and wanted more.

The 1977 Phillies were perhaps the best team in franchise history. They won 101 games. Steve Carlton took home the Cy Young Award. Greg Luzinski finished runner-up in the NL MVP. All but one starter hit .280 or better, and the one who didn’t, was Mike Schmidt, who hit .274 with 38 homeruns and 101 RBI. They averaged the third most runs per game and had the fourth best team average on offense and posted top ten numbers in team ERA, runs allowed and walks issued. This was as complete a team as any in Phillies history.

They won the NL East for the second consecutive year, and faced the Dodgers with a chance to go the World Series. After splitting games 1 and 2 in Dodger Stadium, the Vet welcomed the Phils home for the next two games. Game 3 was THE place to be. First hand accounts tell of the noise inside the concrete slab echoing off the walls. And the Phillies fed off the atmosphere. They rattled Burt Hooton to three consecutive bases loaded walks in the second inning to take a 3-2 lead.

With the game tied at 3, the Phillies scored twice off Elias Sosa in the bottom of the 8th to take a 5-2 lead. That’s when the game turned on its head.

Phillies Manager, Danny Ozark, inexplicably did NOT remove Greg Luzinski for defensive purposes, as he had done so often throughout the 1977 season. The typical defensive upgrade, Jerry Martin, remained on the bench. As fate often has it, the ball found Luzinski in the 9th. Luzinski misplayed a fly ball and overthrew second base, allowing a run to score on the play, and runners to advance. The next batter, Davy Lopes, hit a grounder off Mike Schmidt at third base, which Larry Bowa scooped up and threw to first. Lopes was ruled safe on a bang-bang play. With the benefit of replay in 2025, Lopes may have been ruled out, and the inning over. The following at bat, Gene Garver tossed a wild pickoff attempt, and Lopes scored on a base hit a few pitches later.

The Dodgers would go on to win Game 3 and take Game 4, winning the series 3-1.

So, what happens if the Martin enters the game and, presumably, makes the catch? The Phillies go up in the series 2-1 with the clincher chance the following night. Even if they lose Game 4, they still have a chance at winning the decisive Game 5. They don’t lose two in a row with a 2-1 lead, especially with Steve Carlton on the mound, at home, in one of those games.

The Phillies would have gone on to play the New York Yankees in the 1977 World Series. Of the Phillies teams that fell short, as we’ll see a few more on this list, I do believe the 1977 Phillies would have had the best chance of winning the World Series.

6. What If… Zack Wheeler never signed with the Phillies

Zack Wheeler signed a 5-year, $118M deal with the Phillies prior to the 2020 season. It was a fairly sizable more at the time, especially for a good, not great, starting pitcher who had battled injury and consistency in the past with the Mets. No one could have predicted the player the Phillies were obtaining when they signed Wheeler in 2020.

Since joining the team in 2020, Zack Wheeler has been the model of consistency and has claim to being the best starting pitcher in MLB over the last six seasons. In his time with the Phillies, Wheeler is second in wins, behind just Framber Valdez. He leads all pitchers across MLB in innings pitched and WAR. He’s second in the league in strikeouts. Among starters who have thrown at least 700 innings since 2020, Wheeler ranks 1st in WHIP and average exit velocity, 2nd in opponent batting average and hard hit percentage, 3rd in K/Bb, 4th in BB/9 and HR/9, and 8th in K/9.

To say that Zack Wheeler has been dominant since joining the Phillies might be an understatement.

What happens to the Phillies in the last six years if Wheeler choices to remain a New York Met? A lot.

First and foremost, the Phillies likely do not get to the 2022 World Series. They might not even make the 2022 Postseason without Wheeler. Wheeler gave up just five earned runs in 25.1 innings pitched in the Wild Card round, NLDS and NLCS leading up to the World Series. They simply don’t have the stability at the top of the rotation that Wheeler has provided for the last six seasons.

The crown jewel of the 2020 Offseason was Gerrit Cole, who the Yankees signed for well over $300M. It’s no secret the Phillies were interested in Cole that Winter. But was Cole interested in the Phillies? My guess: No. At least not in the same breath as the Yankees.

Do the Phillies pivot that Offseason, looking to sign another veteran free agent arm before 2020? It’s certainly possible. And the likeliest replacement… Madison Bumgarner. Bumgaren signed a long-term deal with the Diamondbacks that same Winter, but found just a small percentage of the success Wheeler has. Bumgarner went 15-32 with a 5.23 ERA over four injury riddled seasons with the D-backs.

Their other choice would have been to wait a season, and find an arm prior to the 2021 season. That would have been a foolish plan. The free agent starting pitching was nowhere near what Cole and Wheeler have provided. Their best play if they waited would have been, none other, than Taijuan Walker, inevitably signing Walker two years earlier than the team actually did.

I don’t think it’s hard to determine what happens if the Phillies don’t sign Zack Wheeler. He’s getting better with age. He’s showing no signs of slowing down. And he’s steadily climbing the list of all-time Phillies free agent signings, if he’s not there already.

5. What If… The Phillies never traded Ryne Sandberg

Prior to the 1982 season, the Phillies moved highly touted prospect, Ryne Sandberg, as part of a deal that included Larry Bowa, in exchange for Ivan de Jesus.

Many questioned the move at the time. Everyone questions the move today. Sandberg went on to play 16 seasons with the Chicago Cubs, picking up nearly 2400 hits, winning nine consecutive Gold Gloves, seven Silver Sluggers and was named the 1984 NL MVP. Ivan de Jesus, meanwhile, played 3 seasons with the Phillies, batting .249, producing an identical .319 on base percentage and slugging percentage.

To say it was a less than stellar Phillies tenure is one thing. To give up a future Hall of Famer for that production is another.

How does Ryne Sandberg help the Phillies if they don’t trade him? The Phillies have a Hall of Fame second baseman on their roster for well over a decade AND the Ivan DeJesus experience never happens. The 1983 Phillies get 700 ABs of .261/.316/.351/.667 wth 8 HR and 48 RBI with 37 SB from Sandburg as opposed to 565 ABs of .254/.323/.336/..659 with 4 HR and 45 RBI 11 SB form Ivan de Jesus.

Does Sandburg help the offense in 1983 go up against the Baltimore Orioles in the World Series? de Jesus had 2 hits in 25 ABs in the Series. Granted, no one hit. The Phillies hit .195 as a team, losing four straight after winning Game 1. Maybe Sandberg isn’t the propellor to a 1983 World Series win, but the following years likely aren’t as lean with Sandberg. The Phillies core from the 1976-1980 run began to disband, and the team never won more than 86 games in a season the rest of the decade. But having a then 23-year-old Sandberg could have helped soften the blow a little bit, and perhaps forced the Phillies to think a little more competitively. Sandberg could have conceivably played shortstop for the Phillies, while Juan Samuel manned second base. That middle infield would have been something special.

4. What If… Cole Hamels was himself in the 2009 World Series

The Phillies won the 2008 World Series. That’s the last year that sentence in true, unless you’re playing MLB The Show. That’s not entirely important to this What If, I just wanted to remind you.

What is important is the role Cole Hamels played in winning the World Series in 2008. He was the NLCS and World Series MVP, winning four of the five starts he made that Postseason. He gave up just seven earned runs over 35 innings pitched. He was a catalyst to their success in 2008.

But the Hamels we saw in 2009 did not match the one from a year prior. And for a team that was poised to make another World Series run, the Phillies really need Hamels to be more than he was in 2009. That year, Hamels was 10-11 with a 4.32 ERA. His WHIP went up. His strikeouts went down.

So the Phillies, in need of a starting pitcher anyway due to Jamie Moyer’s struggles in the rotation, sought help from an unlikely source: Pedro Martinez. The 37-year-old joined the Phillies rotation in August and made 9 regular season starts before the Postseason. Martinez was a lift the Phillies needed, going 5-1 with a 3.63 ERA in those 9 starts. He followed that up with seven shutout innings in the NLCS against the Dodgers.

More on Pedro in just a moment. This scenario is about Hamels.

The Phillies won the NLCS against the Dodgers, and found themselves back in the World Series for the second straight year. Behind another stellar Cliff Lee outing, the Phils took Game 1 in New York. This is where Hamels come in. If the Phillies felt comfortable with Hamels pitching Game 2, which would have been on 8 days rest since his last start, they would have been able to slot Pedro into Game 3 at home, as opposed to in Game 2 in the city that he famously referred to the Yankees as his “daddy” some years prior.

With a stronger Hamels, the Phillies have chance to leave New York up 2-0, instead of a with a split. They eventually found themselves down 2-1 after the bad Hamels start in Game 3. If they win one of those two games, and go up 2-1 in the series with Game 4 and 5 at home, the pressure would have shifted to the Yankees. While we cannot predict the Game 4 blown save by Brad Lidge, it still would have been 2-2 heading into Game 5.

I do think Phillies win the 2009 WS with a good Cole Hamels. Despite the Phillies hitting .229 as a team, I think the pressure gets put on the Yankees if Hamels delivers. The bullpen wasn’t nearly as good as it was in 2008, but I think Hamels changes the dynamic of everything. 

3. What If… the Phillies didn’t collapse in 1964?

To a 31-year-old writing this article, the 1964 Phillies are just another piece in the lure of the worst franchise ever. To an older generation, the 1964 Phillies were the biggest heartbreak of their fandom.

Heading into September, everything was going the Phillies way. Jim Bunning had thrown a perfect game on Fathers’ Day. The team was 5.5 games ahead of the Cincinnati Reds for the National League Pennant. Life was good.

Until it wasn’t.

The Phillies lost 19 games in September, including ten in a row from September 21-30, as they watched their lead slip away in the National League. Not only did the Phillies end up falling behind the eventual NL winners, the St. Louis Cardinals, but they drew even with the Cincinnati Reds, finishing tied for second in the NL with 92 wins. The St. Louis Cardinals went on to play in the 1964 World Series, defeating the New York Yankees in seven games.

So let’s turn the tables on a year the Phillies didn’t collapse. Let’s assume the Phillies stay afloat enough to win the National League. What happens? The Phillies go on to win the 1964 Pennant and go to the World Series for the first time since 1950. The Phillies had a slightly worse offense than the Cardinals, but a slightly better team ERA. The Phillies had Jim Bunning. The Cardinals had Bob Gibson. Not quite 1968 Gibson, but a really good Bob Gibson.

Do the Phillies go on to have the same success as the Cardinals that Fall?

No. I think the 1964 Yankees, the last World Series title winner to feature Mickey Mantle, beat the Phillies in the Fall Classic. The Phillies overplayed their skillset in 1964. In 1965, they won just 85 games and 87 games the next year, but were never really in contention for the Pennant.

There actually isn’t much of a fallout here, but more of a lightning in the bottle scenario. The Phillies fall to 0-3 in the World Series, twice losing to the Yankees. The Yankees would now have 28 World Series. But I do think, had the Phillies gotten to the World Series, regardless of outcome, this team would be held in reverence by the fans. They might have fallen short, but the adoration would be there.

2. What If… the Phillies didn’t trade Cliff Lee in 2009?

On December 16, 2009, the Phillies went all in by acquiring Cy Young winner, Roy Halladay, from the Toronto Blue Jays in exchange for a trio of prospects, headlined by Kyle Drabek.

But on the same day, the Phillies sent 2009 ace, Cliff Lee, who they acquired just a few months prior, to the Seattle Mariners to “restock the farm system”. The Phillies received, among others, Philippe Aumont, in the deal.

Both Halladay and Lee went on to have excellent 2010 season. Halladay won 21 games, including throwing a perfect game against the Marlins, on his way to the 2010 NL Cy Young Award. Lee, meanwhile, was 12-9 with a 3.18 ERA, splitting time between the Mariners and the Texas Rangers, who he helped get to the 2010 World Series.

What could have happened, though, if the Phillies decided to not care about the farm system in that moment and keep both Halladay AND Lee? There’s no question, the Phillies would have had the best rotation in baseball in 2010, headlined by Halladay and Lee, and a resurgent Cole Hamels, who was much Hamels-esque after the dreadful 2009 we talked about earlier. The real-life Phillies won 97 games that season, and it stands to reckon that the team with Lee added to it from the jump might have crossed the 100 win mark.

The likeliest scenario? The Phillies don’t acquire Roy Oswalt at the Trade Deadline, and instead, go into the 2010 Postseason feeling fine about Halladay, Lee and Hamels in any series.

But do they win the 2010 NLCS? How about the 2010 World Series? I actually have more faith in them winning the World Series than actually getting there. If we’re being honest with ourselves, it’s probably not the ripple effect we imagine. Pitching wasn’t the problem in the 2010 NLCS; the offense was. They hit .216 as a team that series and struckout 56 times in 6 games. They were 8-45 with RISP.  I still think the Phillies lose to the Giants.

1. What If… The Phillies score some runs in Game 5 of the 2011 NLDS?

A generation has 1964. Another has 1993. I have 2011.

The Phillies were unquestionably the best team in MLB in 2011. Prior to the season, they signed Cliff Lee in free agency. They had the best rotation in all of baseball. And even with the departure of Jayson Werth in free agency, the offense was still a force. If 1977 was the best Phillies team ever, this team was second. Or vice versa. There’s no wrong answer.

Winning 102 games, a franchise record, the Phillies took control of NL East in April with an 18-8 record and never relinquished it. Their worst record in any month was 16-14 in September. They didn’t have a single losing month. So heading into the Postseason, expectations were World Series or bust for this Phillies club.

That’s when they ran into the St. Louis Cardinals, a Wild Card team that got into the Playoffs on the final day of the regular, with an 18-8 record in September, and some help from the Phillies. The Phillies beat the Braves, the team the Cardinals needed to lose, in Game 162, to vault St. Louis into the Postseason.

Game 1 went according to plan. While Doc gave up a trio of runs in the first inning, the Phillies put an 11 spot on the Cardinals to win 11-6. Game 2 looked to be effectively the same. The Phillies spotted Cliff Lee four runs after the first two innings, but the Cardinals chipped away for three in the 4th, one in the 6th and one in the 7th, to snatch Game 2, and home field advantage, away from the Phillies.

The pair split the next two games for a decisive, winner-take-all Game 5.

Roy Halladay vs Chris Carpenter.

The two veterans and former teammates toed the slab, and went eye-to-eye, pitch for pitch all night.

Rafael Furcal hit a leadoff triple to open the ballgame. Skip Schumaker drove him in. It was 1-0 Cardinals. No one could have guessed that’s how the game would have ended.

Chris Carpenter tossed a complete game, 3-hit shutout that propelled the Cardinals to the NLCS and eventually, the World Series.

But what happens if the Phillies get a couple runs for Doc before the 9th inning?

The first, and almost assuredly, biggest reversal isn’t the outcome of the game. It’s the health of Ryan Howard. If the Phillies lead after 8, and secure the lead in the 9th, they don’t need to hit in the bottom half of the inning. Howard never comes to the plate, and never tears his Achilles.

The second, is the outcome. The Phillies go on to play the Milwaukee Brewers in the NLCS, who the Cardinals beat 4-2. The Phillies were only 4-3 against the Brewers during the regular season, but 2 of 3 losses were in April. They swept Milwaukee in September. The Brewers scored 26 runs on Cardinals pitching, something they wouldn’t have done that against the Phils. St Louis scored 46 runs against the Brewers in 7 games. The Phillies would have beaten Milwaukee. 

Do the Phillies beat the Texas Rangers in the World Series? Maybe, maybe not. But they have a REALLY good chance. They would have been the favorites going into the Series. Texas’ staff posted a 4.65 ERA against the Cardinals in 7 games. If the Phillies could do equal damage, their pitching staff likely quells the Rangers enough to win the Series.