What if the Penguins traded for T.J. Oshie in 2015 instead of Phil Kessel?

Here’s a fun angle that might be new to you...Set your mind back five years ago to the summer of 2015. The Pittsburgh Penguins were looking for a big upgrade on the wing to help boost their team. Under Jim Rutherford, they’ve never been afraid to search high and low and try to pull off big trades.

In reality, as well all know, this ended up culminating with Pittsburgh acquiring Phil Kessel from the Toronto Maple Leafs. But it almost didn’t work out that way.

What if the Penguins ended up acquiring trade target T.J. Oshie from the St. Louis Blues instead?

Pensburgh has heard for years now from multiple people in and around the organization that would know such things (seriously, listen to the podcast!) about Pittsburgh’s interest in Oshie. The Pens explored in-depth talks with St. Louis about a swap. The Blues had felt their team had grown stale after three straight first round playoff exits and were ready to move on from Oshie. (Which, indeed they did that off-season).

In fact, one credible report we heard was that the Pens were talking about almost exactly the same package they ended up sending out for Kessel — most notably having prospect Kasperi Kapanen and a future first round pick on the table, as well as Nick Spaling mainly to balance the salaries. This was what was in discussion about sending to St. Louis for Oshie. That part always floored me, and there was multiple source confirmation the Oshie to Pittsburgh proposals were shaping up to be about 100% similar to the actual trade made for Kessel.

Much like the Toronto negotiations, young defensemen Olli Maatta and Derrick Pouliot were both considered untouchable in 2015 and not a part of any trade consideration.

Ultimately, the concurrent talks with STL and TOR ended when Pittsburgh and Toronto struck a deal for Kessel. It was made possible by the Leafs retaining 15% ($1.2 million annually) of Kessel’s $8.0 million salary cap hit. Oshie at the time had two seasons left on a contract with a $4.175 million cap hit.

If Toronto had balked in the final stages of the salary retention, there’s a very, very real chance Pittsburgh wouldn’t have been able to make that math work. In that event, the Pens would have pivoted to completing negotiations with St. Louis for Oshie instead, since Pittsburgh was intent on upgrading their team.

That would be an interesting change in the paths of history if it was Oshie and not Kessel who was the big pickup for the Pens. Many fans are repulsing right now, no doubt. “Eww, T.J. Oshie?” you’re probably thinking.

But those same reasons you dislike him on another team would be the same reasons you love him on your team. Oshie is basically a younger, right-handed version of Chris Kunitz (with a pretty snazzy forehand-backhand deke to boot). Add that for Sidney Crosby or Evgeni Malkin to work with? That would be pretty fun.

Of course, Pittsburgh can have no complaints about the reality of the situation. Kessel scored 303 points in his four seasons with the Pens. Oshie would go onto be traded to the Washington Capitals just one day after Kessel went to Pittsburgh (which isn’t a coincidence on the timing of that trade being finalized after STL missed out on a bigger potential return from Pittsburgh) and Oshie scored 208 points in his first four seasons with the Caps.

Really, if all this went down and the Pens grabbed Oshie, the Caps would have figured to be the big losers in this micro-change of plans. Washington likely wouldn’t have had the cap space or future assets to make a run for Kessel and would have had to search elsewhere to some unknown route to upgrade their team. Or they would have stuck with their status quo of keeping Troy Brouwer for another year, being as he was the main piece sent to the Blues for Oshie.

Toronto would be another big loser if they couldn’t flip Kessel with his high salary and their desire to bottom out. It ended up working well for them, since Kapanen has become a useful NHL player and without Kessel they won the draft lottery in 2016 to be able and secure Auston Matthews and really turbocharge their rebuilding. Such an effort eventually made them agree to take Spaling and eat six years of retention on the contract they regretted signing Kessel too at the end of the day.

Still, what could have been wasn’t to be in this world, as the Pens did opt to swing a deal for Kessel instead of his fellow American forward in Oshie. But it was probably closer to happening than many realize, which makes it another possible hypothetical world to have explored. Deep down, there’s probably a million potential trades that were “this close” to happening, that didn’t happen when plans change or another avenue is taken instead.

Pretty remarkable to think about the differences in how the NHL would have played out. Perhaps any (or all) of the 2016, 2017 AND 2018 Stanley Cup championships end up in different places if the Pens would have completed their trade to add T.J. Oshie.