Biggest Questions to Ask the Top Decision Makers of Philadelphia Sports

There are plenty of questions and curious minds about the future of Philadelphia Sports. All four of the major professional sports teams are in very different situations, with unique problems facing the teams heading into the 2027 calendar year.

While the Eagles season is going downhill, the 76ers are now the most popular team in Philadelphia. After a frustrating end to the Phillies season, and the deflating start for the Flyers' campaign, Philly Sports fans are full of mixed emotions.

As a result, there are plenty of unknowns about what the future holds for Philly Sports fans with so much uncertainty about their favorite teams. So if I could ask each team's top executive ONE QUESTION....

My Top Questions For the Eagles, Phillies, Flyers, and Sixers Top Executives

Yes, if I could inject truth serum into these men, and guarantee I got ONE ANSWER from each, this is what I would ask, and why:

(Photo by Stacy Revere/Getty Images)

Q: Dear Howie Roseman, when you drafted Lane Johnson fourth overall in the 2013 NFL Draft, it laid the groundwork for 12 years of elite Offensive Line play that was the foundations of three Super Bowl teams. But now with numerous injuries and retirements over the last few years, how do you plan to rebuild what you to be the cornerstone of this franchise's success on the field?

There have been many times over the last 10 years that the Eagles top Front Office Executive has said that great NFL teams are built through the trenches. Since the 2016 NF Draft, the Eagles have drafted 17 Offensive Lineman, and eleven of those men have started multiple games for Philadlephia over the years.

But in the aftermath of Lane Johnson's retirement, trading Cam Jurgens to Baltimore, and Landon Dickerson's injury history, the Eagles have some difficult decisions to make about what used to be the strength of the team, is now a weakness.

But aside from drafting Lane Johnson in 2013, Howie Roseman's most important addition to the Offensive Line was in Free Agency in 2016. The signing of Brandon Brooks stabilized an offensive line that was in flux in the aftermath of the Chip Kelly era. Brooks was a 6'5" Guard who became the protype for Philadelphia drafting players like Dickerson, Jack Driscoll, and Tyler Steen in future years.

Howie Roseman needs to find that next veteran impactful Offensive Lineman this offseason, the Brandon Brooks for the next era of Eagles football.

(Photo by Bob Levey/Getty Images)

Q: Dear Dave Dombrowski, for years you have talked about how the Phillies are a "good club", but they haven't gotten back to the League Championship Series since 2023. You have put this organization in a bind with so many big contracts handed out to aging players like JT Realmuto, and Aaron Nola, while deals with players like Tijuan Walker, Nick Castellanos, and Brad Keller have not paid off in ways anyone had hoped for. Why should Phillies fans believe you are the man to retool this roster and get the team back to being contenders?

Yes, I know this is a loaded, big picture question, but I believe Phillies fans are losing their patience with this organization, and the team's top executive is not exactly giving anyone confidence in the future.

Sure, Aiden Miller and Gage Wood could be at the Major League level in the next couple of years, but there's no guarantees that either player will be what the experts say their potential is. Remember that Alec Bohm, Bryson Stott, and Justin Crawford were all 1st round draft picks, but none of them have ever consistently played up to their potential.

This roster needs help in many areas: Bullpen help, Outfield overhaul, reliable Right Handed Bats, and maybe even another Starting Pitcher for depth. Look at the teams that have won the World Series in recent years, they all have plenty of depth in their lineups and pitching staffs. The Phillies are too top-heavy, and the depth issues need to be addressed ASAP.

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Q: Dear Danny Briere, since Chris Pronger in 2010, only two Flyers Defeneseman have tallied at least 50 points in a season. We all can agree that Mark Streit (2014-15), and Shayne Gostisbehere (2017-18) are not the answer to why it has been over 15 years since Philadelphia has played with an elite blue line player. When is the Flyers franchise going to upgrade their defensemen, and stop hoping for the best?

Anyone being honest knows that the Flyers defenseman have been a weakness for over a decade, and their defensive rotations seem to struggle no matter if the Head Coach is Rick Tocchet, John Tortorella, Alain Vigneault, or Dave Hakstol.

So if changing the Head Coaches isn't helping make the defensemen better at playing defense (I know, what a wild concept), then maybe we need to stop asking Travis Sanheim, Ivan Provorov, and Rasmus Ristolainen to be the Flyers' version of Zach Werenski or Roman Josi.

I don't care about the prospects and what the young guys can develop into, because I have 10-plus years of seeing this organization fail to produce one elite defenseman. Guys like Éric Desjardins, Chris Pronger, Kimmo Timonen, and Mark Howe were not drafted by Philadelphia. So if past Flyers teams needed to acquire an elite defenseman, then what is the current Flyers' braintrust waiting for, and why are they hoping their draft picks fill the void?

(Photo by Mitchell Leff/Getty Images)

Q: Dear Mike Gansey, this Sixers team has been so much fun to watch, credit to you and your Front Office team on a great offseason. But the 76ers still have one major flaw on the roster that we must address before the NBA Trade Deadline: How long will you wait to acquire a backup Center for Joel Embiid, and address the rebounding deficiencies of this roster?

This isn't breaking news, but the Sixers are not a great rebounding basketball team. Through the first two weeks of the NBA season, there are 22 teams that average more Rebounds per game than the 76ers (42.2 Rebounds per game).

I understand that no one foresaw Ariel Hukporti sustaining a season-ending injury, but everyone knew that rebounding was a weakness of the roster last year. Adding LeBron James and Jaylen Brown fixed other issues with the team. But if Philadelphia goes into a playoff series against the Cleveland Cavaliers, Detroit Pistons, or New York Knicks, they will be struggling to compete for rebounds.

So can the 76ers please add some Front Court depth, so we can stop asking soon-to-be 42 years old LeBron James to play minutes at Center.