1. Bobby Hull / Chicago Blackhawks
In 1972, Bobby Hull decision changed the NHL and the nature of contract forever. Chicago Blackhawks offered Hull a multi-year contract for $250,000 a year to play, $100,000 a year as a coach and $1 million as a GM. Blackhawks didn’t take the offer seriously, but Hull did take it seriously. He signed and started in WHA. This move opened the door to other NHL players to demand larger contracts. Owners were forced to pay them in fear of moving to other leagues.
2. William Nylander / Toronto Maple Leafs
In 2018, a dispute arose between William Nylander and Toronto Maple Leafs. But eight minutes before the deadline, the two sides agreed on a multi-year deal. Nylander was willing to be out of the season due to the contract. The likelihood of being traded wasn’t imminent. But Nylander was almost coming close to be the first NHL player since Michael Peca to miss an entire season due to contract dispute.
3. Danny Heatley / Ottawa Senators
His dispute came one year into his six-year contract with Ottawa Senators. According to ESPN, Heatley requested to be traded in 2009, though he had already signed a $45 million deal a year ago. Senators reached an agreement with Edmonton Oilers, but Heatly refused the deal. He was eventually traded to San Jose ending his long drama.
4. Ken Dryden / Montréal Canadiens
In 1973, Ken Dryden wanted to walk away from Montreal Canadiens. CBC indicated that Dryden didn’t take the offer kindly and he sat out an entire season and returning to his law study at McGill University. However, Canadiens realized his importance after failing to defend the Stanley Cup title. They signed him, and he helped the team with four Stanley Cups.
5. Alexei Yashin / Ottawa Senators
According to Baltimore Sun, Alexei Yashin refused to play for Senators during 1999-2000 season. He thought he would walk in as a free agent after sitting out for a whole year of his final contract. However, this didn’t work out; an attorney said he owed Senators another year. He was forced to play and later, he was traded to New York Islanders for a deal that included Zdeno Chara and Jason Spezza.
6. Steve Larmer / Chicago Blackhawks
Larmer dispute with Blackhawk cost made him not to make history in the NHL. In 1980 to 1990, he played 884 games for Chicago and need one more season to break Doug Jarvis 964 record. He, however, didn’t want to remain in Chicago, but Blackhawks refused to trade him. He missed the first 13 games of the 1993-94 season and thus lost his streak. He was later traded to New York Rangers where they won Stanley Cup.
7. Mark Messier / New York Rangers
He helped Rangers win the Stanley in 1994. Mark took advantage of that and wanted the management to offer him a new deal. He refused to return to training camp due to the contract deadlock. But a few days after the league started, Messier agreed to a new contract despite rumors of trade.
8. Ryan O’Reilly / Colorado Avalanche
In 2013. O’Reilly and Colorado held out for a better contract. They then signed a two year $10 million from Calgary Flames. They later improved the deal to two years $12 million in 2014. The dispute ended in 2015; the O’Reilly was sent to Buffalo Sabres.
9. Brendan Shanahan / New York Rangers
Brendan Shanahan was a combative player for New York Rangers in the 2008-09 season. He sat out half of a season after failing to come to an agreement with Rangers for a suitable deal. New York never offered him another deal, and so he ended to New Jersey Devils in 2009.
10. Barry Trotz / Washington Capitals
CBS reported that Coach Barry Trotz and Washington Capitals were involved in a contract dispute 11 days after winning the 2018 Stanley Cup.
Trotz resigned for feeling underpaid and undervalued. He ended signing with New York Islanders for more than a double of what Capitals were offering him.