The Pittsburgh Penguins aimed for a postseason run in the 2023-24 season after missing the playoffs in 2023 but fell short of expectations, failing to secure a playoff spot. Now, they face a decision: build for a future without Sidney Crosby or give the veteran captain another shot at a championship.

Recently, the Penguins acquired forward Kevin Hayes and a second-round pick in the 2025 NHL draft for future considerations, suggesting they are opting to support Crosby’s pursuit of another Cup. Last season, they added veterans such as defensemen Ryan Graves and Erik Karlsson, and forward Lars Eller. This offseason, Pittsburgh brought in Kevin Hayes.

Nonetheless, the Penguins might still look to add younger players who can contribute both now and in the future. Tristin McKinstry of Clutch Points sees Toronto Maple Leafs forward Nicholas Robertson as a potential trade target. Robertson, who completed his entry-level contract and became a restricted free agent on July 1, remains unsigned as of July 15.

Penguins GM Kyle Dubas drafted Nick Robertson in Toronto when he was the Leafs’ GM from May 2018 until moving to Pittsburgh in 2023. Dubas selected Robertson with the No. 53 pick of the 2019 NHL draft. McKinstry suggests this prior relationship could facilitate a reunion in Pittsburgh.

Since debuting in the 2020-21 season, Robertson has played 87 regular-season games, scoring 17 goals and 17 assists. In the 2023-24 season, he tallied 14 goals and 13 assists in 56 games but did not score in six playoff games. Reports indicate that Robertson has requested a trade due to struggles and injuries in Toronto, seeking a fresh start.

NHL insider Chris Johnston confirmed that Robertson informed the Maple Leafs of his decision not to sign a contract extension before free agency on July 1. Maple Leafs GM Brad Treliving acknowledged Robertson’s frustration and affirmed the player’s value and opportunity in Toronto.

In an interview with Sportsnet’s Luke Fox, Robertson expressed uncertainty about his future with the Leafs, indicating his agent would handle the negotiation process. AFP Analytics projects Robertson to sign a two-year, $2.7 million contract with a cap hit slightly above $1.3 million. According to PuckPedia, the Penguins have $3.5 million in cap space, enough to complete a sign-and-trade for Robertson if they pursue him.