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NHL REGRET ALERT: The Montreal Canadiens used bad strategy and lost Shea Theodore

In the 2013 NHL Draft, the Montreal Canadiens sat with the 25th overall selection after a season that ended in a conference finals loss. Looking to toughen up for a heavy, hard-hitting Eastern Conference, the organization reached for size and physicality. They selected Michael McCarron, a 6-foot-6 forward from the U.S. National Development Team. One pick later, the Anaheim Ducks took Shea Theodore, a skilled, puck-moving defenseman. That single-slot decision has aged into one of the clearer strategic missteps of the Carey Price era.

Drafting McCarron aligned with the Canadiens’ thinking at the time. The team wanted bigger, more aggressive forwards who could match the physical brand of play then dominating the East. McCarron drew comparisons to Milan Lucic—a strong, punishing presence. Offensively he had not been a high producer with the U.S. program, but he had accumulated more than 200 penalty minutes across two seasons, signaling the edge the Canadiens prized.

McCarron did not reach the NHL until 2015 and spent most of that first professional season with the Canadiens’ AHL affiliate. His most substantial stretch with Montreal came in 2016-17, when he appeared in 31 games, recorded five points, and delivered 76 hits. After that, he bounced between the NHL and AHL, hampered by injuries and limited opportunity. In the 2019-20 season the Canadiens traded him to the Nashville Predators, receiving Laurent Dauphin in return. Dauphin lasted one year in the organization before moving on to Arizona. During McCarron’s time in Montreal the club reached the playoffs only once and exited in the first round. Since leaving, McCarron has shown improvement, but the Canadiens retained neither him nor any lasting value from the deal.

Contrast that trajectory with Theodore’s. The defenseman made his NHL debut in 2015 and by 2016-17 was already playing more games in the league than in the AHL. Facing the expansion draft, Anaheim traded him to the Vegas Golden Knights to protect other assets. In Vegas, Theodore thrived. He consistently produced more than 40 points per season, contributed to a Stanley Cup championship in 2022-23, and later made his Olympic debut with Team Canada at the 2026 Winter Olympics.

One of the defining failures of the Canadiens’ recent history is the inability to win a Stanley Cup during the peak years of Carey Price. A mobile, high-skill puck-moving defender such as Theodore would have offered a different kind of support for that goaltender and the team’s transition game. While Theodore is not a heavy physical presence, his speed, vision, and offensive contributions from the blue line could have altered Montreal’s competitive trajectory—potentially helping the club reach the playoffs more consistently and remaining a valuable piece long after the Price era.

Instead, the Canadiens invested in a size-and-physicality strategy that yielded limited NHL production, frequent injury and roster instability, and eventually a trade that brought back little lasting return. The player selected one slot later developed into a Cup-winning, Olympian-caliber defenseman. The gap between those two outcomes underscores how a single draft preference for grit over skill can compound across a decade of contention windows that never fully opened.