The Flyers have had their fair share of bad luck when drafting. Whether it's taking players who came with injury concerns or those who never panned out, there is a long list of former prospects that did not work out.
Some of the biggest came during the tenure of former GM Ron Hextall. Hextall is to thank for players like Travis Konecny, Travis Sanheim, Noah Cates, and Sam Ersson. But when you look at some of his other picks, most people are left scratching their heads.
He wasn't afraid to take big swings with some of the early picks. That can work out at times, and it makes the team look like geniuses. Most of the time, though, it blows up in their faces. Unfortunately for Hextall, it did the latter more often than not.
Sometimes it's bad luck. But when it happens consistently, it becomes a pattern. So while Hextall did give the Flyers more than a few franchise players, the team could be in much better shape if he had made different choices.
There is one that may be at the top of the list for one of the worst picks of Hextall's tenure. Jay O'Brien was ranked as an early-to-mid second-round pick. Hextall did well with Joel Farabee, taken with one of the picks from the Schenn trade. But it was another risky pick when O'Brien was selected 19th overall in 2018.
Entering his draft year, he starred for Thayer Academy, posting a whopping 80 points in 30 games. That was 21 more points than his next closest teammate. Once he turned to the collegiate game, he struggled. He lasted 25 games for Providence College before turning to the BCHL the next season. It looked like he found his game again with the Penticton Vees, posting 66 points in 46 games.
Heading to Boston University, O'Brien posted modest numbers during his three seasons. But for a first-round pick, he never stood out as a strong producer. He ended his Boston career with 26 goals and 70 points in 79 games. Not terrible, but not great either.
The Flyers elected not to sign him, and he would later sign an AHL deal with the Toronto Marlies, but missed the entire 2023-24 season to injury. O'Brien signed with the Charlotte Checkers this past year, was sent to the ECHL, but never played.
Most of the players drafted after O'Brien have not necessarily stood out. Isac Lundeström has been a decent depth forward for the Ducks and will try to do the same for Columbus. Rasmus Sandin has improved his game since moving from Toronto to Washington two seasons ago. The best of the bunch was K'Andre Miller, who was traded from the Rangers to Carolina this offseason.
O'Brien was always an odd pick at that time. Only two players taken after him in the first round have yet to make their NHL debut. Most players have over five professional seasons under their belts.
The fact that he still has not made his professional debut speaks volumes as to why this is likely one of, if not the worst, pick in franchise history.