We are back with our first formal NHL Saturday piece in awhile, as it is postseason time, and our local San Jose Sharks are not participating for the eighth spring in a row. That’s sad, considering prior to 2020, the Sharks had only missed the playoffs six total times in their franchise history, dating back to their 1991-1992 expansion season. So, yeah, it’s been an extremely long dry stretch in Silicon Valley, but as we’re exploring today, there are bright spots on the horizon if the San Jose front office doesn’t blow it now.

That’s because the Sharks defied the draft lottery odds to snag the No. 2 overall pick—the third time in three years the team has landed a Top 2 pick. San Jose struck gold with Macklin Celebrini in 2024, and the jury is still out on No. 2 overall pick Michael Misa (2025), although the early returns were not good. Faced now with the probable selection of Swedish sensation Ivar Stenberg, the San Jose organization has an amazing chance to stockpile top talent and build for the next decade plus, really.

We immediately think of two teams in the last two decades who were in similar positions: the Pittsburgh Penguins (2002-2006) and the Edmonton Oilers (2010-2016). The Pens used five straight years of Top 5 picks to build a team that won three Stanley Cup titles (2009, 2016–2017), while the Oilers had seven consecutive Top 7 picks—including four No. 1 overall picks—to construct a team that reached the Cup Finals in both 2024 and 2025. The Sharks should consider themselves capable of either outcome now.

The draft rules are different now, too, so getting five or more straight years of premium picks is no longer possible; plus, the Sharks were on the brink of the postseason this year, and they probably can make the leap back to the Stanley Cup playoffs in 2027, meaning no more high draft picks to build on this streak of good fortune. So it’s even more important now to nail this No. 2 pick, which is why random chatter about the San Jose front office trading the pick should be sheer nonsense, considering the past.

Let’s examine what Pittsburgh did right:

  • 2002, Pick 5: defenseman Ryan Whitney (traded away mid-2009 before team’s Cup win)
  • 2003, Pick 1: goaltender Marc-André Fleury (62 playoff wins, 10 playoff shutouts, three Cup titles)
  • 2004, Pick 2: center Evgeni Malkin (Calder winner, Hart winner, three Cup titles)
  • 2005, Pick 1: center Sidney Crosby (two-time Hart winner, three Cup titles)
  • 2006, Pick 2: center Jordan Staal (one Cup title, traded after 2012 season)

The Penguins really only nailed three of these five picks—and yet that talent was enough to form the core for three NHL championships over a nine-season stretch, which also included one Eastern Conference Finals appearance in 2013. We marvel at the fact Pittsburgh could get so fortunate in three straight drafts to get three future Hall of Fame players; what Fleury, Malkin, and Crosby were able to accomplish as transcendent talents is amazing, and any team should be so lucky to find themselves so blessed.

Which brings us to Edmonton next:

  • 2010, Pick 1: left wing Taylor Hall (traded after six seasons, won Hart in 2018 with New Jersey)
  • 2011, Pick 1: center Ryan Nugent-Hopkins (804 points in 1,031 games in 15 seasons with the Oilers)
  • 2012, Pick 1: right wing Nail Yakupov (111 points in 252 games with Edmonton, out of the league after six seasons overall)
  • 2013, Pick 7: defenseman Darnell Nurse (324 points in 798 games in 12 seasons with the Oilers)
  • 2014, Pick 3: center Leon Draisaitl (Hart winner)
  • 2015, Pick 1: center Connor McDavid (three-time Hart winner, six-time scoring champion)
  • 2016, Pick 4: right wing Jesse Puljujärvi (112 points in 317 games with Edmonton, only 70 games with three other teams)

The first three No. 1 picks were all underwhelming, especially Yakupov who was traded away for little after four seasons. Hall didn’t flourish until he left the Oilers organization, and Nugent-Hopkins has never been a star despite being a moderately productive player with the team for a long time—and being a part of the two Western Conference title teams, too. The same could be said for Nurse, although much more probably was expected from both those long-term team contributors and middling guys.

Clearly, the team nailed the Draisaitl and McDavid picks, while totally whiffing on the final premium pick in this sequence. We know not all drafts are created the same, and we also know generational talents are not sitting atop each draft board every spring. It’s a hit-or-miss proposition to begin with, and then a team has to hit on what it can when it can. Considering four of these seven picks have been players the team has kept for the duration of their respective careers, the Oilers did about as well as the Penguins.

Winning a Cup is also a random thing at times; it can be said more often than not that the Cup wins you rather you winning the Cup (apologies to the U.S. Open golf tournament, where we think the phrase originated). Again, both the Pens and the Oilers did decently with their draft fortunes, and now the Sharks would love that kind of success, even if across a shorter span of premium draft picks. Celebrini has been great, while Misa is not trending well, historically speaking in terms of sabermetric value, at all.

San Jose has to nail this No. 2 pick: the top pick goes to the Toronto Maple Leafs, who probably will pick Gavin McKenna, leaving Stenberg for the Sharks. Is he a lock? No. But if Misa manages to become even as productive as Nugent-Hopkins, that would be a plus. Then adding Stenberg to the equation and hoping he becomes something in the ballpark of Celebrini, San Jose could have a great foundation for the next ten seasons, at least. All this in conjecture, but we have to wonder how the Sharks feel.

To recap:

  • 2024, Pick 1: center Macklin Celebrini (178 points in 152 games, 18.7 career Point Shares in two seasons)
  • 2025, Pick 2: center Michael Misa (21 points in 45 games; 1.9 Point Shares in one season [15th on the team])

The best the Sharks and their fans can hope for is Celebrini continuing to set records, Misa developing into something at least as good as Nugent-Hopkins, and taking Stenberg at No. 2 watching him blossom into something like Hall—while still with San Jose.