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On This Day: End Of An Era

May 16 is a day in Penguins history that saw the Ray Shero regime come to a crumbling and humiliating end.

2012 NHL Entry Draft - Rounds 2-7 Photo by Justin K. Aller/Getty Images

With the Penguins now in full offseason mode, we’ll be starting a fun “On This Day” series that chronicles some of the best (or worst) moments in Penguins history on any given day.


Ray Shero’s tenure as Penguins general manager was filled with positives, negatives, and everything in between.

Reaching two Stanley Cup Finals with a youthful squad led by Evgeni Malkin, Kris Letang, Marc-Andre Fleury and Sidney Crosby and winning one of those two Cups against a very experienced Red Wings team obviously highlights the positives.

Stanley Cup Finals - Pittsburgh Penguins v Detroit Red Wings - Game Seven Photo by Jim McIsaac/Getty Images

And the inclusion of millions of draft picks in aggressive trading techniques saw the prospect reserves of the Penguins limited to the likes of Beau Bennett and Joe Morrow, with diamonds in the rough such as Matt Murray and Bryan Rust.

One theme of Shero’s time as GM, whether directly his fault or not, were his Penguins teams flaming out in the postseason, no matter how stacked he tried to make his roster (hello, Douglas Murray, Brenden Morrow, and Jarome Iginla).

His time as GM reached its breaking point on May 16, 2014. Fresh off their second-round series defeat at the hands of the New York Rangers, a series that saw the Penguins go up 3-1, only to lose 4-3, the Penguins began to overhaul the organization, starting with Ray Shero. Many, many fans will say Shero’s termination was long overdue, as the heart-wrenching loss to the Rangers marked the 5th straight year that the Penguins were eliminated by a lower seeded team.

He would leave the Penguins organization with a record of 373-193-56.

Longtime front office member of the Carolina Hurricanes, Jim Rutherford, was appointed to the position on June 6, 2014. Rutherford would go on to relieve head coach Dan Bylsma of his duties on the same day he assumed the GM role.

Shero would remain out of a job until May of 2015. He became the general manager of the New Jersey Devils on May 4 of that year. While in New Jersey, he has continued with his aggressive approach to player acquisition. He is responsible for: acquiring Taylor Hall (for Adam Larsson), signing highly touted college prospect Will Butcher, trading for Sami Vatanen, and drafting Nico Hischier.

Shero’s rebuilding process would become somewhat of a slow burn for the Devils. However, the fruits of his labor may be starting to return results. The team returned to the Stanley Cup playoffs in 2018, but were eliminated in the first round by the Tampa Bay Lightning.

And of course, the Penguins moved on from Ray Shero and after a bumpy ride in the short-lived Mike Johnston era, the team would go on to do some pretty cool stuff.

All in all, Ray Shero’s 8 years in Pittsburgh will likely be highlighted by the Penguins not winning enough with the superstars still in their primes. But was the organization better off with their constant playoff struggles? Jim Rutherford and Mike Sullivan probably don’t come aboard. It’s a possibility that the back-to-back Cup runs don't exist, either.

It’s definitely a fun thing to think about, especially now that the Penguins have had all this success in recent years.

During a time where many thought “the window” was finally being shut for the Crosby/Malkin era, May 16, 2014 may be remembered as a blessing in disguise for the Penguins and Ray Shero alike.