The Pittsburgh Penguins enter the offseason with a laundry list of decisions that will mold their future on the ice. These choices hold the potential for a transformative impact, but addressing the Penguins’ shortcomings requires courage rather than caution. The team must acknowledge its problems, even if it means confronting beloved players who have become part of the issue. Despite good intentions, some recent acquisitions have exacerbated issues rather than solving them. The stagnant power play was a symptom, not the root cause of the Penguins’ struggles. A lack of scoring wingers and a declining shot at the point from Evgeni Malkin highlighted deficiencies that also affected even-strength play. Only after the arrival of Michael Bunting did the Penguins’ second line show signs of life. The power play improved slightly but remained inconsistent and prone to surrendering shorthanded goals. The third line failed to generate offense, with the exception of Lars Eller. They struggled to find the net in 3v3 overtime situations despite the open ice and speed. The defense displayed glaring weaknesses at critical moments, and the team’s mental fragility led to wild inconsistency. Such teams squander third-period leads, concede goals immediately after scoring, allow shorthanded goals while struggling with a stagnant power play, and crumble under pressure. Otherwise, the Penguins were flawless. General Manager Ron Hextall admitted his surprise and disappointment at the Penguins’ lackluster performance before and after the NHL trade deadline. Despite the presence of experienced leaders, the team teetered on the brink of folding their season in early March. Sidney Crosby initially dragged the team forward, but it was ultimately up to them to pull themselves out of the mire. Now, the Penguins must confront uncomfortable realities head-on instead of sidestepping inexplicable shortcomings. They possess approximately $10 million in cap space for July 1 but are not in a position of strength. To improve more than teams like the New Jersey Devils, Buffalo Sabres, Washington Capitals, and New York Islanders, Hextall will need to take calculated risks. The easy decisions involve contract extensions for Sidney Crosby and Marcus Pettersson, who are set to become unrestricted free agents on July 1, 2025, but can negotiate new deals starting this July. The tough decisions involve the talented players surrounding Sidney Crosby in the lineup. The choices that will shape the Penguins’ future are the as-yet-unknown options to address problems, upgrade weak spots, and reverse negative trends. Creating a more defensively sound blue line, adding middle-six scoring, and lessening the burden on Malkin are just a few starting points for remaking the team and rectifying past mistakes. Last summer, Hextall wisely acquired Reilly Smith as a replacement for the departing Jason Zucker and signed Ryan Graves as a July 1 free agent. These moves were met with little criticism at the time and seemed like logical, straightforward decisions. However, a year later, neither player is considered a clear victory. Quite the opposite, in fact. Hextall acknowledged his dissatisfaction with the trade offerings for veterans with term at the NHL trade deadline. He also expressed regret over not making a mid-season hockey trade that could have altered the team’s sideways trajectory. Perhaps this explains why Smith and others remain with the Penguins despite trade rumors. This summer, Hextall must cast aside the caution that guided his in-season moves. Undoing the mistakes of the past 12 months is paramount. It’s time for the Penguins to trust their instincts and have the courage to make difficult calls that might defy conventional logic for a team seeking immediate success. If the Penguins had embraced risk earlier in the season, such as trading Jake Guentzel for Michael Bunting, they might have awakened from their self-induced lethargy sooner, and the season would still be ongoing instead of a thing of the past. Hextall is unlikely to fully emulate former GM Jim Rutherford’s aggressive approach of making multiple trades in an attempt to fix the roster, but he would be wise to borrow from that strategy to rectify what hasn’t worked despite financial and trade investments. Several players on the Penguins’ roster may be better suited elsewhere. Smith, Graves, and Rickard Rakell are not alone on this list, although Rakell’s past success with the Penguins warrants a more thorough evaluation. Logic might dictate sticking with the current group, as it appears promising on paper. Conventional wisdom might suggest that the trade market is too weak. There will be plenty of obstacles ahead, but the only path forward is through genuine change. There’s no reason to believe the current Penguins are significantly better than the 88 points they finished the season with. It took desperation to turn their season around, but upon closer examination, they still lost four out of 12 games that were essentially must-win (8-1-3). Hextall may not have many good choices. The Penguins lack the coveted draft picks that rebuilding teams seek, and they don’t have an abundance of expendable talent either. The necessary changes will not be easy, and some of them may be unpopular. However, they are absolutely essential. Caution and tepid change will only yield tepid results.