Philip Tomasino is a scoring winger working hard to develop a complete game. After not qualifying him on Monday, the Pittsburgh Penguins delivered a healthy raise and a one-year contract on Tuesday. On Wednesday, Penguins general manager Kyle Dubas signed Anthony Mantha, who is another scoring winger with plenty to prove to a new team.

Suddenly, the Penguins have more forwards who would be more suited to playing a top-six role because they lack the “hard to play against” physicality than they have spots available.

Read More: Penguins Give Bonus Heavy Deal to Anthony Mantha

One could reasonably argue that Dubas has stocked his roster with top-six replacements for the coming trades of the existing top-six wingers, Rickard Rakell and possibly Bryan Rust.

Make no mistake, it would be a significant drop off from Rakell to Tomasino or Mantha, but the 2025-26 Penguins season isn’t about immediate results. Dubas is methodically aligning the stars for big trades that everyone has been anticipating.

Dubas’s patience appears to be winning as the marketplace opens up and his options get more plentiful. And his players become more valuable, which means a greater trade return.

It does not always work out this way–often, teams make trades, then hit the free agent market to plug holes, fill gaps, or find some hidden treasures. Dubas has done the reverse, starting with trying to find some diamonds in the rough, signing forward Justin Brazeau, and re-signing Tomasino.

Now, he’s plugging future holes by signing Mantha. It seems certain that the trades are next.

In fact, Dubas strongly implied this was his timeline on Monday.

“I know more about the free agent market because of the calls we get on our veteran guys–teams saying that the market is nuts, we might have more interest in doing a deal or a trade,” said Dubas. “So we’re gonna evaluate everything, we’re going to do what’s best for the Penguins.”

There is one more shoe to drop before the Penguins’ wingers hit peak value: Nikolaj Ehlers.

The Vegas Golden Knights hijacked the NHL Free Agent Frenzy by acquiring Marner via sign-and-trade. The Florida Panthers let the air out of the balloon by re-signing all of their key players, including 37-year-old Brad Marchand to a ridiculous six-year contract. The Edmonton Oilers cleaned up their street by dealing Victor Arvidsson to the Boston Bruins and signing Andrew Mangiapane. The Anaheim Ducks made a splash with Mikael Granlund. And the Vancouver Canucks stole someone’s thunder when they re-signed Brock Boeser.

According to TSN reporter Chris Johnston, Ehlers will decide between a few teams on Wednesday. As teams fall out of the running for the top remaining winger on the free agent market, the trade market for the Penguins’ assets only gets bigger.

So, on July 2, there are only Ehlers and Rakell left. One team will overpay Ehlers, and Dubas surely hopes one team will overpay the Penguins.

One New Challenge

Teams chasing the Stanley Cup and feel like they are legitimately on the shortlist of teams able to compete for it have altered their strategies based on the very unique salary cap spikes. Never in the NHL’s salary cap era has the salary cap gone up by as much and is projected to keep going up as much as this year and the next few years.

Ordinarily, Stanley Cup contenders chase veterans with proven track records, then fill in the remainder of the roster spots with what cap space might be left over.

However, teams like the Carolina Hurricanes and Edmonton Oilers are chasing the restricted free agents that Dubas planned to chase–and the contenders can spare more prospects, spend more draft picks, and have more urgency to acquire players such as K’Andre Miller or even prospect Isaac Howard than do the Penguins.

It’s a good strategy. Imagine the Penguins of the 2010s had pursued the same strategy instead of chasing players like Derick Brassard, Jarome Iginla, David Perron, Jason Zucker, and Patrick Marleau.

Hindsight is 20/20, and it seems there has been a shift by some forward-thinking GMs to learn the lessons of Stanley Cup winners of the recent past to add young players instead of veterans.

It doesn’t make much sense for Dubas to spend prospects and young players when that’s exactly what he’s trying to acquire. It becomes a lateral move for the Penguins but not so for Edmonton or Carolina who don’t need quantity, but can focus on small-batch quality.

It’s yet another challenge for the Penguins in a rebuild that is about to begin the most painful part.