The Toronto Maple Leafs and Pittsburgh Penguins should make a deal, but unfortunately it may not be for who you want.
If I were to play Fantasy GM and make a trade between the Leafs and Penguins, it would 100 percent include Sidney Crosby or Evgeni Malkin but unfortunately that's not going to be happen. Although the Pens are set to be a bottom-feeder in the NHL once again this year, it feels like Crosby and company will finish their careers in the black-and-gold and not chase another championship.
If Crosby had never won a Stanley Cup, then it would make sense to chase a ring, but realistically what else does he have to prove? If he gets traded to another organization and the team loses in the First Round, doesn't that just tarnish his reputation? If he instead stays loyal to Pittsburgh and does the same thing that Mario Lemieux did, helping the next young crop of players grow, then that shows his true colours which I think is more important.
With three Stanley Cups, multiple awards and gold medals, Crosby is a first-ballot Hall-of-Famer and arguably a "Mount Rushmore" NHLer of all-time, so whether or not he wins again won't really matter.
With Crosby and Malkin most likely off the table, the Leafs should go after the team's best other forwards in either Rickard Rakell or Bryan Rust. Both players make around $5M for the next two full seasons, so their contact's are incredibly valuable, especially as they're both top-six forwards.
Leafs and Penguins should make a deal
If the team were to target either player, I feel like they would be more interested in Rust, primarily because he plays a tougher style of hockey and has a little bit more playoff experience. In 79 playoff games, Rust has 35 points and scored some timely goals during the Penguins back-to-back championship runs.
Rakell would obviously be a big addition because he's a three-time 30-goal scorer, but Rust isn't shy to the back of the net, having compiled six straight 20-goal campaign's himself. He's also been a beneficiary of playing a lot of time beside Crosby over the years so jumping to the Leafs and playing alongside Auston Matthews wouldn't be an intimidating factor to him as well, so he should be able to shine well beside the captain and Matthew Knies.
The only issue that Toronto has when it comes to trading with Pittsburgh is that Kyle Dubas is the current GM, so he may have some resentment towards doing a deal with the Leafs, but at the same time, Dubas is familiar with the Leafs system so there may be a player he's interested in acquiring. Maybe he believes in Nick Robertson or maybe it's another prospect that he drafted that he wants back in Pittsburgh's system, but that could be an opportunity for Toronto and Dubas to strike a deal.
It probably won't happen for another few months but the Leafs should jump on Rust before another team looks to scoop him up at the NHL Trade Deadline.