What Are Philly Sports’ 15 Most Gut-Wrenching What If Moments

For long-suffering Philadelphia Sports Fans, the last 15 years have been a wild rollercoaster ride filled with exhilarating highs, depressing lows, and moments when you are wonder what is going on.

Since 2010, the Philadelphia Eagles have won two Super Bowl Championships while the Phillies have reached one World Series. Meanwhile, the Flyers have not reached the Stanley Cup Finals in 15 years, and the 76ers haven't gotten past the second round of the NBA Playoffs since 2001.

On Tuesday's edition of The Sports Bash with Mike Gill, the question was asked "What Are The Biggest Philly Sports What If's since 2010". While the listeners on 973 ESPN South Jersey came up with some great answers, there are many storylines that Philadelphia Sports fans seem to want to forget or other topics came to mind more quickly.

These Are The Top 15 What-If Moments In Philly Sports Since 2010

The rules for this list are simple: these events/storylines all happened in the last 15 years, and it has to be situations if things played out differently, would've had major ramifications on Philly Sports History.

15. What if the Phillies never give Scott Kingery that big contract

Before the start of the 2018 season, Phillies General Manager Matt Klentak made a bold move that was the beginning of the end of his time with the Phillies organization. Scott Kingery was selected in the 2nd Round of the 2015 MLB Draft and was the 35th-best prospect in Major League Baseball heading into 2018 Spring Training.

Nicknamed "Scotty Jetpacks", he looked so good in Spring Training that he was given a six-year, $24 million contract before Kingery ever played a game in the Major Leagues. In his first two MLB seasons, Kingery had an underwhelming .243 Batting Average along with a miserable .291 On-Base Percentage and averaged One Strikeout per game through 273 games.

Instead of allowing Kingery more time to develop in the Minor Leagues and following the traditional method of advancing a young prospect, the organization forced him to change his swing and, theoretically, ruined his future. The contract became a huge blackeye for Matt Klentak's reputation as his numerous mistakes led to his firing in 2020.

14. What If The 76ers Don't Draft Jahlil Okafor

When Philadelphia landed the third overall pick in the 2015 NBA Draft, the belief was they would get a really good player. After selecting two Centers in the last two drafts (Joel Embiid and Nerlens Noel), many analysts and fans zeroed in with "The Unicorn" Kristaps Porziņģis. But the Latvian's agent made it clear to the 76ers that his client would not sign with Philadelphia, forcing the organization to pivot.

Jahlil Okafor was considered one of the four best prospects in the 2015 NBA Draft. But he played the same position as other Sixers draft picks Joel Embiid and Nerlens Noel. There were reports that General Manager Sam Hinkie tried to trade the third overall pick but couldn't get the value he wanted.

So Philadelphia drafted a player in Okafor whose style of play didn't fit the modern NBA of Three-point shooting, high-paced play, and athleticism. The "Big Men Experiment" complicated Philadelphia's rebuild and caused angst among an impatient fan base.

13. What If the Flyers win Game One of the 2010 Stanley Cup Finals

Philadelphia's run to the Stanley Cup Finals was unexpected. The team had started four different goaltenders that season, fired Head Coach John Stevens after 25 games, and there were seven teams that finished with more points than the Flyers. But their thrilling comeback down 3-0 in the series versus the Boston Bruins propelled them to the organization's first Stanley Cup Finals appearance since 1997.

While the Chicago Blackhawks were a very talented team, the Flyers were very confident and came out scoring three goals in the First Period. But Chicago would not be embarrased infront of their fans at the United Center and the teams would exchange goals with the score tied 5-5 at second intermission.

But the Flyers took switched Goaltenders during the game while the Blackhawks stuck with Antti Niemi. Chicago scored the only goal of the third period and would go on to win the first two games of the Stanley Cup Finals. If Philadelphia had won Game One, the trajectory of the series could have been different but instead, Philly Fans are still haunted by Patrick Kane goal in overtime in Game 6 that won Chicago the Stanley Cup.

12. What If Ryan Howard Doesn't Tear His Achilles

The 2011 Phillies were supposed to be the team to get back to the World Series after coming short of a deep playoff run the year before. The pitching staff healined by Roy Halladay, Cliff Lee, Cole Hamels, and Roy Oswalt was expected to be the reason Philadelphia made a deep playoff run.

At 31 years old, Ryan Howard was still a feared power hitter even though his statistics had declined from his peak years (2006-2009). This was his sixth straight 100 RBI season and he led the Phillies with 6 RBI during the 2011 National League Divisional Series.

But the St. Louis Cardinals' pitching staff limited the Phillies' offense to a total of six runs in the final three games of the series. Losing 1-0 heading into the bottom of the 9th inning, Ryan Howard came to bat with two outs and the season on his shoulders. His ground out to end the game wasn't the real news at the end of the NLDS: the Phillies slugger tore his Achillies Tendon trying to run down to First Base.

Howard's devastating injury was the symbolic end of the Phillies "big three" era that featured Howard, Chase Utley, and Jimmy Rollins leading the team to the playoffs five straight years, along with two World Series appearances. Howard was never the same power hitter, and the Phillies didn't have another winning season over the next nine years.

11. What if Markelle Fultz never sustained his Shoulder Injury

While most Sixers fans cringed about General Manager Bryan Colangelo trading with the rival Boston Celtics to get the Number One overall pick, the reality is that most Basketball Analysts viewed Markelle Fultz as the top prospect in the 2017 NBA Draft.

Fultz was a dynamic scorer in college whose skill set seemed like the perfect complement to Sixers All-Stars Joel Embiid and Ben Simmons. But the young man who shot 41.3 percent from three-point range in college all of a sudden couldn't shoot when he arrived for Sixers Training Camp.

The pain in Fultz's shoulder that restricted his shooting motion would be diagnosed at Thoracic Outlet Syndrome. There was a plethora of speculation for how the first overall pick injured his shoulder and why delays to his rehab of the injury happened in the first place.

After two miserable seasons in Philadelphia, Markelle Fultz was traded to the Orlando Magic. Once he finally recovered from all the injuries he had sustained, the 6'4" Guard became a solid Guard who could average double-digit points and play high-level defense. But he has never lived up to the expectations laid on him that led to be drafted with the first overall pick in the 2017 NBA Draft.

10. What if the Eagles' Defense doesn't collapse in the second half in Super Bowl 57

Philadelphia had a 24-14 lead over the Kansas City Chiefs in Arizona at Halftime of Super Bowl 57. It looked like the Eagles were on track to win their second Super Bowl Title in five years. But Chiefs Head Coach Andy Reid and Quarterback Patrick Mahomes had adjustments heading into the second half.

The Chiefs outscored the Eagles 24-11 en route to winning Super Bowl 57. Mahomes picked apart an Eagles defense that struggled to get any pass rush on the three-time NFL MVP Award winner. Reid and Mahomes took advantage of Eagles Defensive Coordinator Jonathan Gannon, who continued a trend from the 2022 NFL season.

During the regular season, Gannon either struggled or refused to make in-game adjustments. In wins over the Lions, Cardinals and Packers along with losses to the Commanders and Cowboys, the Eagles Defense got taken advantage of in the second half of those games and Gannon didn't make adequate in-game adjustments.

Those issues were on full display at Super Bowl 57 against future Hall of Famers Andy Reid and Patrick Mahomes. "What If" Gannon had made the adjustments, and "what if" the Eagles Defense were able to get pressure on the Quarterback are big frustrations for Birds' Fans.

9. What if Nolan Patrick was worth being selected second overall by the Flyers

There has been some revisionist history about the 2017 NHL Draft, but the reality is that two of the top prospects that year were Nico Hischier and Nolan Patrick. There was a big debate eight years ago about who should go first and second overall.

When the Flyers drafted Patrick, there was a ton of hype that this player could be the next hockey superstar in Philadelphia. But the consecutive 30-point seasons would not become a precursor for bigger things to come, as health issues brought a dark cloud over Nolan Patrick.

Patrick suffered multiple concussions, which exacerbated his Migraine Disorder that he was diagnosed with in 2019. After only 197 games played over the course of four years, the Flyers traded him to the Vegas Golden Knights in 2021.  At 25 years old, Patrick announced his retirement after all the injuries he sustained became too much for him to overcome.

In recent years, there have been reports that then-Flyers General Manager Ron Hextall ignored the advice of his scouts who wanted the organization to draft Defenseman Cale Makar. Selected two spots after the Flyers selected Patrick, Makar is one of the best defensemen in the NHL today, and many fans bemoan the organization drafting Nolan Patrick in 2017.

8. What If The 76ers didn't accept a hostile takeover by the Colangelo Family

While Sixers Co-Owner and Managing Partner Josh Harris would not be happy with the way I verbalized this "What If", the reality is that Philadelphia Sports fans are very resentful about what Jerry and Bryan Colangelo did to "their team".

When Sam Hinkie was hired to be the 76ers' General Manager and President of Basketball Operations, he was given permission to go ahead with his plans for a major rebuild. But after 3 years of Hinkie's "The Process", NBA Commissioner Adam Silver approached Josh Harris to bring Jerry Colangelo. Harris appointed Jerry as Chairman of Basketball Operations.

Four months later, Sam Hinkie resigned after weeks of speculation that the 76ers would be hiring Jerry's son, Bryan Colangelo, for a role in the Front Office. While Jerry Colangelo publicly washed his hands of any responsibility for what happened with the 76ers from 2015-2018, his son, Bryan, became Public Enemy Number One for Philly Sports fans.

When Bryan Colangelo resigned June 2018, it was after a tumultuous two years that culminated in the revelation that his wife had been using "Burner" Twitter Accounts to leak proprietary information and harass people online. The Colangelos never helped the team get out of the second round of the NBA Playoffs and left the team in disarray.

7. What If The Flyers don't trade Bobrovsky and overpay Ilya Bryzgalov

When Sergei Bobrovsky joined the Flyers organization in 2010, there was a belief that he could become a Championship-Caliber Goaltender. Fifteen years later, Bobrovsky has won two Stanley Cup Championships and has been awarded Vezina Trophies (given to the best Goaltender in the NHL), but none of those accomplishments happened in a Flyers Uniform.

At 22 and 23 years old, "Bob" was a good Goaltender but he was not yet at the level the Flyers needed to be contenders. The organization was trying to "win now," and they didn't want to wait for Bobrovsky to develop. So the Flyers traded the man who was supposed to be their "Goaltender of the Future" to the Columbus Blue Jackets for three draft picks.

Those draft picks turned into Goaltender Anthony Stolarz (who won a Stanley Cup as Bobrovsky's backup in Florida) and Taylor Leier, who scored two goals in 55 games with the Flyers. Meanwhile, the organization gave Ilya Bryzgalov a big contract to be their Franchise Goaltender.

Bryzgalov also only lasted two seasons in Philadelphia, and the Flyers were stuck paying him millions of dollars for the next 10 years. The search continued for a Franchise Goaltender while Bobrovsky has gone on to have a Hall of Fame career away from Philadelphia.

6. What if The Sixers Don't Acquire Andrew Bynum

Before the Sixers hired Sam Hinkie and began "The Process", Philadelphia attempted one more big swing at a Franchise Player outside of the NBA Draft. After years of trying to build around Andre Iguodala, the 76ers organization decided to move on from the 9th overall pick in the 2004 NBA Draft. Philadelphia had the opportunity to acquire an All-Star big man who had won multiple NBA Championships, who was entering his basketball prime.

People forget that Andrew Bynum has the resume of a player that any NBA team would be interested in trading for. His skill set, his statistics, and his accomplishments all trended upward towards being a Franchise Caliber Superstar.

But the Los Angeles Lakers knew that Bynum's immaturity and injury history were deterrents from re-signing him to a long-term contract. The Sixers jumped feet first into a four-team trade that brought Bynum to Philadelphia and sent Iguodala to the Denver Nuggets.

The Lakers, who landed Dwight Howard in the massive trade with numerous players and draft picks flying in different directions. In theory, the Lakers could have sent Bynum to Orlando for Howard, but Philadelphia really wanted to get a new Franchise-caliber player to replace Iguodala.

While Andrew Bynum never played a game in the Sixers uniform due to injuries, Andre Iguodala would go on to win 4 NBA Championships and an NBA Finals MVP Award with the Golden State Warriors. The Bynum failure opened the door for Philadelphia to hire Sam Hinkie and begin the rebuild later called "The Process". But one can only imagine "IF" the Sixers never acquired Andrew Bynum, what would have happened to the organization.

5. What If The Eagles Drafted Russel Wilson

Even though his 76 Passing Touchdowns were only second in North Carolina State History behind Phillip Rivers, the 5'11" Quarterback was getting little interest from NFL Scouts. So Russell Wilson transferred to the University of Wisconsin to show the NFL he could perform in the Pro-Style Offense.

But some NFL evaluators still did not like his height, and some NFL teams didn't like the fact he also had the opportunity to play baseball after being selected in the 4th Round of the 2010 MLB Draft.

There were 5 Quarterbacks selected in the 2012 NFL Draft before the Seattle Seahawks picked Russell Wilson. Thirteen Picks later, the Philadelphia Eagles selected Quarterback Nick Foles at 88th Overall.

The Eagles organization was very high on Wilson heading into the 2012 NFL Draft, and then-Head Coach Andy Reid had Quarterback Michael Vick coming off an injury. Wilson could've been a guy that Philadelphia could develop behind Vick and could've given Reid a longer lifeline with owner Jeffrey Laurie.

In the second round, the Eagles selected Vinny Curry at 59th overall (with a draft pick they got from the Arizona Cardinals in the Kevin Kolb trade). Imagine if the Eagles took Wilson in the second round, does Wilson become to Andy Reid what Patrick Mahomes has been in Kansas City? Does Reid lead Philadelphia to their first Super Bowl instead of Doug Pederson? And what happens to Nick Foles if he's never drafted by the Eagles?

4. What If the Phillies never traded Cliff Lee to the Seattle Mariners

Coming off losing the 2009 World Series to the New York Yankees, the Phillies believed their window to win was still open. Their cornerstone players, such as Ryan Howard, Chase Utley, and Jimmy Rollins were still in their prime while Lefty Cole Hamels was growing into a stud pitcher you can depend on every five days.

One of Philadelphia's key acquisitions at the 2009 MLB Trade Deadline was Cy Young Award Winner Cliff Lee. The left-handed pitcher was expected by Phillies fans to be a key member of the Starting Rotation for years to come.

But Philadelphia's Front Office was concerned about resiging Lee when he became a Free Agent so on December 16, 2009 the organization made two trades:

-Cliff Lee traded to the Mariners for three prospects
-Phillies send three prospects to the Blue Jays for Roy Halladay

While Halladay became an immediate fan favorite and would have one of the best two-year runs of any pitcher in Phillies' franchise history, the loss of Lee to this day perplexes Phillies's fans.

Lee came back to Philadelphia for the 2011 season after he spent his one year away playing in Seattle and Texas. But that one year away, the Phillies lost in the National League Championship Series against a team that had more pitching depth than Philadelphia.

In the 2010 MLB Playoffs, the San Francisco Giants had a big three-pitching staff with Tim Lincecum, Matt Cain, and Madison Bumgarner. The Phillies had Roy Halladay and Cole Hamels but Roy Oswalt was past his prime, and Joe Blanton had a rough start in the 2010 NLCS.

If Cliff Lee was on the Phillies that season, that 2010 NLCS would have gone very differently and Philadelphia would have been the favorites to win the World Series.

3. What if Ben Simmons Makes The Layup In Game 7 versus the Hawks

One of the biggest enigmas in Philadelphia Sports history was the First Overall Pick in the 2016 NBA Draft. Even though Ben Simmons would go on to be a three-time NBA All-Star and two-time All-Defense NBA First Team Selection, his lack of evolution as a player and person turned the Sixers fan base against him.

The 2020-21 NBA season was already a strange situation with teams playing in front of empty or limited attendance arenas and starting the regular season two months later than usual. But what made everything more complicated was Ben Simmons missing 14 games with a mix of personal issues and injuries.

Simmons would have the worst postseason of his NBA career, shooting a horrible 25-74 (34.2%) on Free Throws. The Sixers were the favorites to win their second-round series versus the Atlanta Hawks, but the Sixers were held back from winning thanks in part to Simmons' play in Games 4 through 7.

But the moment that makes 76ers fans cringe is when Ben Simmons had a wide-open layup attempt in the fourth quarter of Game 7 and passed the ball. A liability on both ends of the court, it was the apex of Simmons' fall from top draft pick to scapegoat in the NBA Playoffs.

We would find out later that Simmons had been dealing with family issues off the court and a lingering Back Issue that would force the 76ers to trade him next season. If Ben Simmons makes more Free Throws or could get out of his own head, Philadelphia could have reached their first Eastern Conference Finals since 2001.

One could argue the Sixers would have been better off without Ben Simmons during that playoff run than with him on the court.

2. What If Alshon Jeffery makes the catch versus the Saints in the Playoffs

The 2018 Philadelphia Eagles went through a season with more highs and lows than the previous year which led to the organization's first Super Bowl Championship. After the team started the year with Super Bowl MVP Nick Foles at quarterback, he handed the reigns of the offense back to 2016 Second overall NFL Draft Pick Carson Wentz.

Wentz's 2017 season ended with a major Knee Injury and was the reason he couldn't start the 2018 season. But the organization was still invested in Wentz as the team's future and Foles was asked to accept his role as the Backup Quarterback.

Even though Carson Wentz played well overall, the Eagles were only 4-4 when they got to their Bye Week. Philadelphia wanted to bolster the offense and acquired Wide Receiver Golden Tate before the NFL Trade Deadline.

Wentz's play was erratic after the Trade Deadline and a plethora of injuries led Philadelphia to a 2-3 record heading into NFL Week 15. Team doctors discovered that Carson Wentz had a broken back and another injury ended his season, opening the door for Super Bowl hero Nick Foles to become the starting Quarterback again.

The Eagles won the final three games of the 2018 season, and Nick Foles averaged 320 Passing Yards per game down the stretch of the regular season. After the "Double-Doink Game" in Chicago, many Eagles fans felt like the "odds" or "luck" were on their side. But the offensive struggles in the NFL Playoffs Divisonal Round in New Orleans made it necessary for some Nick Foles magic to win the game.

With three minutes left in the Fourth Quarter, Nick Foles led the Eagles offense down the field and absorbed a Roughing Penalty that put Philadelphia the opportunity for the game-winning touchdown. But on 2nd Down with Ten Yards to go, Nick Foles threw a pass that should've been caught by Alshon Jeffery OR the Saints should have been called for Pass Interference.

The typically sure-handed Wide Receiver was unable to make the important catch and allowed the Saints to steal the ball. If the Eagles won that game, they would have been in a favorable matchup with the Los Angeles Rams and then had a rematch with the New England Patriots.

If the Eagles led by Nick Foles reached a second straight Super Bowl, then Philadelphia never gives Carson Wentz that big contract and instead stick with Foles long term at Quarterback. Also, the Eagles may keep Doug Pederson beyond the 2020 season and Nick Sirianni is never hired.

1. What If Kawhi doesn't make the game-winning shot and the Sixers beat the Raptors

During the Joel Embiid era with the Philadelphia 76ers, the team many people believe was the best shot to make a deep playoff run was the 2018-19 season. This was Elton Brand's first season as General Manager, and he made two major trades to put the Sixers in a position to contend for a Championship.

The acquisitions of Jimmy Butler and Tobias Harris looked like perfect additions to pair with Embiid, Simmons, and sharpshooter JJ Redick. After Philadelphia dominated the first-round playoff series against the Brooklyn Nets, their second-round matchup would be against a Toronto Raptors team that made their own big additions during the season.

After adding NBA Champion Kawhi Leonard in the offseason, the Raptors made a strategic move to acquire Marc Gasol at the trade deadline. The Raptors anticipated they could be facing the 76ers in the playoffs, and Gasol was brought in to help neutralize Sixers' Center Joel Embiid.

Both Joel Embiid and Ben Simmons struggled in the series versus the Raptors,while Jimmy Butler and Tobias Harris had erratic play too. But the Sixers forced a Game 7 and in the final seconds had the chance to win or go to overtime.

The Sixers competed hard to have the chance to tie the game and after Kawhi Leonard missed the second of two free throws, Tobias Harris grabbed the rebound, leading to Jimmy Butler tieing the game with 4 seconds left.

But the man who missed the free throw would redeem himself; Kawhi Leonard caught the ball and took a shot as the clock ran down to zero, the ball bounced on the rim three times before falling through the net. The Raptors would go on to win the NBA Title, and the Sixers would break up a championship caliber.

If Kawhi Leonard missed that shot, the game would have gone to Overtime, and Philadelphia would have been in a position to advance to the Eastern Conference Finals. The Sixers would have been favorites to win the 2019 ECF series versus a young Milwaukee Bucks team. A 76ers team that reaches the NBA Finals is not being overhauled in the offseason, and Jimmy Butler would not have been sent out of town in a sign-and-trade to the Miami Heat.

While Jimmy Butler led the Miami Heat to two NBA Finals appearances, the 76ers still cannot get out of the second round of the NBA Playoffs. The ultimate "What If" would have impacted the futures of four to five different NBA Franchises, not just the one located in Philadelphia.

Speaking of Philly Sports History, some of the most controversial figures over the last 30 years are also some of the men named above. Do you agree with these rankings?