For the past 16 seasons, right winger Jarome Iginla has been one of the National Hockey League’s most beloved players. Lauded for his professionalism, class and generous nature, Iginla is noted for his lengthy tenure as captain of the Calgary Flames, his “aw-shucks” demeanor and his goal-scoring. Fans all around the NHL – even in Edmonton, where the hometown boy suited up for the rival Flames – have cheered Iginla’s exploits for years.

Given his treatment by the fans in the past, the lack of tears over his departure from Calgary and arrival in Pittsburgh in late March are hardly surprising. He’s getting on in age – he turns 36 on Canada Day, July 1 – and his former bosses and teammates in Calgary noted his improved chances at winning a Stanley Cup in the Steel City. Flames general manager Jay Feaster was complementary towards Iginla’s participation in the trade process, alluding to the fact that the club could’ve lost Iginla to the free agent market for nothing on July 5.

Much like Ray Bourque’s quest in the springs of 2000 and 2001, Jarome Iginla’s chase for the ever-elusive Stanley Cup – literally the only championship Iginla hasn’t won in hockey – has become one of the sport’s most intriguing storylines down the stretch. Now, two months after Iginla became a Penguin, he’s four wins away from his second trip to the Stanley Cup Finals. However, the road to the finals goes through Boston, and a team and fan-base he miffed during his whirlwind final day in the Calgary Flames organization.

Centre Alex Khokhlachev, D Matt Bartkowski and a 1st. That’s the talk, still unconfirmed. Sounds like Boston is the team for Iginla. — Mark Spector (@SportsnetSpec) March 28, 2013

Later that evening, with the east coast nestled firmly in their beds, Feaster officially announced that Iginla had been traded. But instead of heading to Beantown, as Boston’s fans, media and management were led to believe when they turned in for the night, he was heading to Pittsburgh – in exchange for Kenny Agostino, Ben Hanowski and a first round pick.

If you listened carefully, you could hear dozens of Bruins fans and media awaken with startled expressions. When Iginla and the Penguins made their way to the TD Garden on April 20, for the first time in his NHL career, he was greeted with loud boos and jeering from the Boston fans.

Iginla roundly booed when he touched the puck. Took until there was 3 minutes left in the period which shows type of game he’s had. — Chris Stevenson (@CJ_Stevenson) April 20, 2013

The game was in many ways par for the course for Iginla, given his recent performances – 16 minutes of ice-time, primarily at even-strength, three shots, a power-play goal and a first-period fight with Nathan Horton. The Penguins won 3-2.

In the absence of Iginla, the Bruins kept Bartkowski, Khokhlachev and their first round pick. They went out and acquired the legendary Jaromir Jagr instead – sending prospects Lane MacDermid, Cody Payne and a conditional pick (a first rounder now that the Bruins are in the final four) to Dallas for his services.

Bartkowski has become a crucial component for the Bruins, helping out on their battered blueline. Jagr hasn’t entirely clicked with the Bruins while Iginla has gradually improved in Pittsburgh following a shaky beginning. Jagr has 4 points through two tight rounds for Boston, while Iginla’s 12 points have him sixth in league scoring. As the Eastern Conference Finals approach, no doubt several Bruins fans will look at the performance of the two players and ponder what would happen had Iginla opted for Boston instead – one could argue that Jagr’s finesse game would play better in Pittsburgh, while Iginla’s rugged play may have fit in better in Boston. Notions of what could’ve been no doubt will fuel the reactions of the TD Garden crowd throughout the series.

Eight weeks after nearly becoming a Bruin, and six weeks after his most recent visit to Boston, Jarome Iginla and the Pittsburgh Penguins will tangle with the Bruins in the Eastern Conference Final. Iginla will face being a reviled figure for the first time in his playing career, with a trip to the finals at stake. Given how evenly matched these two teams are, how Iginla reacts to the negativity could very well determine the outcome of the series – and whether he finally gets a Stanley Cup ring.