On Aug. 6, 2023, new Pittsburgh Penguins general manager Kyle Dubas pulled off a shocker. He acquired reigning Norris Trophy winner Erik Karlsson from the San Jose Sharks.

This deal wasn’t a straight-up one-for-one package. No, this transaction involved nine players, three draft picks, and three teams.

Supposedly, the Penguins had completed the heist of the century. Karlsson was just voted the top defenseman in the league. He collected 76 assists to finish tied third in the NHL behind Connor McDavid (89), Nikita Kucherov (83), and Leon Draisaitl (76).

Meanwhile, Karlsson was the 11th player to surpass 100 points, becoming only the sixth defender in league history to amass that many points in a single season. He finished the year with 101 in 82 games.

However, when we look back at the three teams involved in this trade, none made the playoffs, with Pittsburgh close, while San Jose won the draft lottery.

Let’s revisit this massive trade a year later and determine if anyone has won the deal yet.

Pittsburgh

Karlsson had a rough start to his Penguins career, tallying only 11 goals and 56 points in 82 games. He was plus-4, an improvement on his minus-26 from the season prior, but his production fell 55 points, and he went from a draft lottery team to a club that should have been Stanley Cup contenders.