Five years ago, a seismic shift rocked Madison Square Garden. On May 5, 2021, the New York Rangers fired team president John Davidson and general manager Jeff Gorton, promoting associate GM Chris Drury to take the reins. It was a move that promised a new era for the Blueshirts—and it’s been a wild ride ever since.

“Chris is a very sought-after executive and a strong leader,” owner James Dolan said at the time. “We are confident he will effectively guide the team to ensure the long-term success we promised Rangers fans.”

So, how has Drury fared? The story so far is a tale of two extremes. On one hand, the Rangers have come within two wins of the Stanley Cup Final twice, electrifying a fanbase hungry for glory. On the other, they’ve missed the playoffs in each of the last two seasons—including a disastrous Centennial campaign that saw the team fall out of contention before the NHL’s Olympic break in early February.

Drury, who signed a contract extension in March, still holds full authority over hockey operations. And now, he’s pinning his hopes on the NHL Draft Lottery. The Rangers have an 11.5 percent chance of landing the No. 1 overall pick—a shot they owe, ironically, to one of Drury’s best moves. Instead of trading this year’s first-rounder in the J.T. Miller deal last January, he opted to keep it, sending the 13th pick to Vancouver instead.

But for many Rangers fans, the question lingers: Is Drury the man to lead the team back to relevance? After a season that fell far short of expectations—following a historic 2022-23 campaign that saw the team set franchise records with 55 wins and 114 points, earning the Presidents’ Trophy—the pressure is on. The ping-pong balls will tell part of the story Tuesday night, but the real work is just beginning.