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Some hits, near misses and what-could-have-beens in Penguin history

Billy G a Capital? TJ Oshie a Penguin?

Pittsburgh Penguins v Washington Capitals - Game Five Photo by Len Redkoles/Getty Images

One of the fascinating things about the NHL is that the way communication goes, teams are constantly and consistently having ongoing conversations about players. Trades aren’t usually made on a whim (unless you’re Chris Pyror and Ron Hextall and jump to grab Mikael Granlund, anyways), but often come as a result of weeks if not months of talking and exchanging ideas until the trigger gets pulled.

Today, we look into a few such examples of what could have been

Billy G, a Capital?

Set your watch back to February 2009. The Penguins had just fired Michel Therrien. Dan Byslma had taken over and started out 6-1-1 in his first eight games as coach, but Pittsburgh still wasn’t in a playoff spot. That was mighty disappointing considering the Pens came within two games of winning the Stanley Cup the prior summer. Sidney Crosby was out at the time with a wonky groin. Long gone were veterans like Marian Hossa, Ryan Malone and Gary Roberts, with their influence on and off the ice being missed big time. The Pens needed something. Miroslav Satan had a decent looking stat-line 17 goals and 19 assists but was uninspiring and sent to the minors to clear cap space (in an era where the full cap hit could be buried penalty-free in the AHL).

That gave general manager Ray Shero enough room to add Islanders captain Bill Guerin. At 38, he was literally a gray beard. He was almost a Washington Capital as well. Guerin was a healthy scratch for trade purposes for two games — and back in 2009 that wasn’t a common occurrence like it is today to shelf players in advance of a trade, let alone a respected captain. But negotiations between Washington and NYI fell through. As ESPN told it:

A deal reportedly was done with an Eastern Conference contender, and Guerin had waived his no-trade clause.

But nothing had happened by Monday, and he again was not in the lineup when the Islanders played the Colorado Avalanche that night.

As it turns out, the original deal fell through, Guerin said during an interview with TSN of Canada.

“It was a pretty painful process,” Guerin said on TSN. “We thought we had a deal done with another team a couple of days ago. We were just waiting for something to happen. But this is a great opportunity for me, going to a talented team like that [in Pittsburgh].”

Shero and the Pens swooped in, and it was one of the best trade deadline pickups possible, especially for the trade cost. The Pens gave up a conditional pick: a fifth rounder if they didn’t make the playoffs, a fourth if they did get in, and a third rounder if the Pens won a round and Guerin played half the games. They would end up giving up the maximum amount, but it would be well worth it. Guerin scored five goals and 12 points in 17 regular season to help the Pens qualify for the post-season. (The Islanders, by the way, used the pick they got to draft a goalie that they elected to not sign and got nothing out of the deal).

Guerin recorded six points in the second round series against Washington, including an overlooked but important second period goal in Game 7 to push Pittsburgh out to a 3-0 lead and help start the blowout win.

What would happen if Guerin was on the other side of that series? We will never know, but it’s not a stretch that the late and somewhat unexpected add for the Pens was crucial in their run for the first Stanley Cup in the Sidney Crosby era, and possibly the difference in advancing to the Eastern Conference Final. The Caps wouldn’t get that far for almost another decade.

TJ Oshie, a Penguin?

In the summer of 2015, it was well-reported that St. Louis was looking to shake up their team by trading away T.J. Oshie. The Pens were involved in negotiations, and perhaps as leverage with Toronto over Phil Kessel or just covering their bases if in need of a backup plan, Pittsburgh reportedly was close to sending to the Blues the main pieces of what they were offering to Toronto (2014 first round pick Kasperi Kapanen and a future first round pick) to acquire Oshie.

As it happened, eventually the Maple Leafs agreed to eat some of Kessel’s salary and take Nick Spaling from the Pens to help even out the money and make a deal work. So the Pens made that trade with Toronto and picked adding Kessel over the opportunity to get Oshie.

Just one day after Kessel went to Pittsburgh, the Blues moved on and made their trade to send Oshie to Washington for the lesser return of Troy Brouwer, a goalie prospect and a third round pick.

Kessel would go onto help fuel the Pens to two Stanley Cups in the next two years. Oshie would come good in Washington, where he remains to this day. Brouwer only played one season in that stint with St. Louis, but they would win a Cup down the line anyways. Not that anyone would have guessed at the time, but the three teams involved with Oshie would go onto earn the next four Cups.

(And, funny enough, the Blues would eventually get Kapanen anyways on waivers way down the road in 2023).

It could have shaken out differently, with the Pens getting Oshie and Kessel remaining in limbo in Toronto. But it didn’t.

Knies, the one who got away

When Ron Hextall and Brian Burke came to Pittsburgh, one thing they said (but didn’t really do) was to emphasize wanting to add bigger and tougher players. Hextall’s first draft pick in Pittsburgh was in the second round in 2021. It has been whispered and confirmed recently by Elliotte Friedman that the Pens were zeroing in on drafting Matthew Knies - a 6’3, 210 pound power forward at pick No. 58.

The only problem was that Kyle Dubas and the Maple Leafs nabbed Knies at pick No. 57, just before Pittsburgh was up. The Pens had to pivot and draft Tristan Broz, a forward who didn’t fit at the University of Minnesota (where, ironically, Knies ended up flourishing) and Broz transferred to Denver for this past year.

Knies would go onto develop quickly and turn pro in time for the 2023 playoffs, showing well and looking like the successor in the Zach Hyman-Michael Bunting mold in Toronto as a complimentary scoring winger on a top line while adding skill and some jam with his big frame.

That one pick alone would not have saved Hextall’s job, but the Pens would in a better spot if they had Knies. Instead, they don’t, and Pittsburgh still hasn’t drafted and developed a quality NHL forward for themselves since Jake Guentzel in 2013 (apologies and caveats to Dominik Simon, Sam Lafferty, Daniel Sprong [who made it three teams later] and Kapanen [who did his developing in the Toronto organization before returning to the Pens]).

As the wheel turns, that will be one area where Dubas will be looking to reverse now that he is with the Penguins to add a future solid forward — perhaps as soon as the first pick in the upcoming 2023 draft.

Which makes for a humorous and circuitous route in hockey to show what could have been, almost was, and actually happened when often the same cast of characters are involved for decisions that shape the teams and future.