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Five players I wish won the Stanley Cup with the Penguins

A look at players we wish would have won the Cup with the Pens.

Alexei Kovalev and Matrin Straka skate on the ice

The Pittsburgh Penguins have won more Stanley Cups since 1990 than any other team in the league. It’s a wonderful and charmed life to be a Penguins fan. Unfortunately though, you can’t win it every single year. Here’s a list of players we wish could have been champs in Pittsburgh, no particular order.

#1 Marty Straka

Straka deeks

Martin Straka was the Pens 1st round pick in 1992. He made the NHL for the 92-93 season, immediately after being drafted. He even had a 30g+34a season his second year in the NHL! Somehow he got traded to Ottawa in 1995 for a lackluster return of defenseman Norm MacIver and center Troy Murray. Hockey blogs and twitter would have roasted GM Craig Patrick for that one, had they been around.

Straka would bounce between 3 teams (OTT, NYI, FLA) in the next three seasons, not really finding his footing and signing as a free agent with the Pens for the 1997-98 season, after Mario Lemieux retired and the Jaromir Jagr influence was really turning Pittsburgh into Prague West with plenty of Czech players.

This is where Straka would become a legend, scoring 279 points (101g+178a) in 308 games in the next four seasons in Pittsburgh from 1997-2001, in some of the toughest years to score points in the clutch-and-grab days of the NHL’s trap era.

For as great as Jagr was in the crucial 1999 first round playoff series against the Devils (the one the Pens badly needed to win to make more money and help their bankruptcy), Jagr was limited to playing 3 games of that series. Jagr is in franchise lore for playing on a bad groin and scoring in OT of Game 6 to force a Game 7, but it was Straka (6g+5a in the series) that really fueled the Pens.

Straka was a crowd favorite for his size. Or lack of it, listed generously at 5’9 and 180 pounds. To make it in pro hockey, Straka countered this by being one of the fastest skaters in the game, and had tremendous hands and offensive ability. If you never saw Straka, picture Conor Sheary. Now picture him more consistent and with more of an edge and with better hands, vision and playmaking. That’s basically Marty Straka.

Straka was traded away in November 2003. His Pens career spanned parts of 10 seasons and ended up being for 560 games, 165 goals, 277 assists for 442 points in 560 games. He was also a great playoff player scoring 70 points (26g+44a) in 106 games, with 2 OT goals including this series winner in 2001 against the Capitals.

#2 Jiri Slegr

Capitals v Penguins X Dahlen

My list, my rules. I always liked Jiri Slegr. The original #71 in Pittsburgh.

He won a Cup in Detroit in 2002, as something of a franchise whipping boy during that run (sorry he wasn’t a hall of famer like everyone else on that team). He also won the 1998 gold medal along with Jagr and Straka in the Czech’s great triumph in Nagano.

Basically he was a buddy of Jagr’s who tagged around and ended up having a great career. He could skate, he had good size. His offensive instincts weren’t Paul Coffey but Slegr was OK. Defensively he wasn’t a rock but he was solid. Then and now, the Pens weren’t really known for defensemen, but something of Slegr’s style always drew me in. He was a smooht player in his day and a fun one to watch.

#3 Colby Armstrong

The Pens class clown and jokester, Armstrong’s cruel fate and purposes in Pittsburgh was being used as trade bait in the franchise-altering trade that brought Marian Hossa to the Pens. Instead of Armstrong ascending with the young, growing Pens team, he was cast off to Atlanta, where his career would flounder and he wouldn’t see the playoffs from after 2007 with the Pens until all the way in 2013 in his final NHL season.

Armstrong was the first beneficiary of a “Crosby bump” when the former 2001 first round pick was called up to the NHL in 2006 and got his first taste of action in the show playing mainly with Sid on the dreadful 2005-06 team. Armstrong put up 40 points (16g+24a) in 47 games and appeared to be the 1st line right wing of the future with Crosby. That wasn’t to be as his production dried up in the year that followed and he was demoted into a checking line role.

Armstrong was (and is) such a jovial character and good guy, you just wanted to see great things happen for him and for it to all pay off. Unfortunately it never really did.

#4 Ryan Malone

A rare bridge player from the X-Generation days to contending team, Malone is the only forward to have played multiple seasons as a teammate to both Mario Lemieux (2003-04, 2005-06) AND Sidney Crosby/Evgeni Malkin (2006-08).

Malone only played 299 career games as a Penguin, in hindsight it certainly feels like that should have been a higher number. In those games though, he was an important piece; a winger with size, toughness, a nose for the net and some good hands. He could kill penalties, he could post up in front of the net on the power play. He could play left wing or right, on a scoring line or a checking line.

Malone’s shining moments was in the 2008 playoff run where he recorded 16 points (6g+10a) in 20 games, good for 4th on the team trailing only Crosby, Malkin and Marian Hossa. His legacy was cemented in Pens lore when he kept battling and grinding despite a face suffering a broken nose, swollen lip and chipped teeth as a result of being hit with the puck in front of the net.

Malone, along with R.J. Umberger, was also at the head of kids who grew up in Pittsburgh playing hockey and starting to make it to the NHL. It’s a proud tradition that has only grown over the years and would have been really cool if he could have won a Cup with his hometown team.

It wasn’t to be though, Malone’s exquisite 2008 playoff performance put him in-line for a huge raise as he entered unrestricted free agency. The Pens, now and ever, did not have a ton of salary cap move and prioritized signing Brooks Orpik and attempting to sign Hossa at the start of free agency, so they traded Malone’s rights to Tampa. He signed with them and played there for parts of six seasons.

#5 Gary Roberts

Gary Roberts was at the tail end of an illustrious career when he was traded to the Pens in spring of 2007. Pittsburgh was a young team on the verge of making the playoffs for the first time in the Crosby/Malkin era. They needed some vets to show them how to play. Along with guys who would follow with Stanley Cup experience like Bill Guerin, Petr Sykora and Chris Kunitz; Roberts led by example with fiery leadership and a wonderfully fun domination of the Ottawa Senators franchise.

Gary Roberts as Pen was on the cutting edge of memes and twitter. He would have been even bigger later on in the social media era. The old Pensblog pranks of John Fedko’s call-in show in adulation of Roberts were some of the funniest and best jokes around back then.

Whether it was his legendary diet and training programs (which still carry on to this day for many NHL stars), or beating up someone almost half his age, scoring a big goal, throwing a big hit, openly bullying a referee, Roberts was a one of a kind player that any fanbase would fall in love with.

The team fell short in 2008, which ended up as Roberts’ final NHL postseason appearance. He went with Malone to Tampa in 2008-09 but ended up retiring that season.


Who’s on your list? The writer of this list is 34 and you would probably guess that from the list above. Older fans might have names of pre-Lemieux players and have just as valid (if not moreso) due to their perspective having a longer time.


When a guy who has won 2 Cups with the Pens tells you the list needs an addition, the list needs an addition.

#6 John Cullen

Cullen, like Armstrong, is lost in the shuffle since he was the main piece traded to get the Pens Ron Francis and Ulf Samuelsson back from Hartford. Cullen put up 94 points in 65 games as a Penguin in 1990-91 before being traded. As Peter Taglianetti noted, Cullen’s leadership and scoring ability was a prime reason Pittsburgh was competitive for a playoff spot that season, and Phil Bourque once said it “broke his heart” Cullen couldn’t have been a part of the championship team...So yeah, that’s probaly a big whiff on my part to not have him included in the first place.