Any critics who act as though they came out of nowhere are only fooling themselves and will continue to play the role of fools the longer they refuse to acknowledge what\u2019s plain as day: The Canadiens have entered their window to contend for the Stanley Cup. And, with that, it may be somewhat foolish to bet against them\u2026 but, if one absolutely must (say, if you\u2019re a Toronto Maple Leafs fan), these, the likeliest candidates to regress in 2026-27<\/a> are the ones to bet against specifically:<\/p>\n Cole Caufield<\/p>\n Add an asterisk beside Cole Caufield\u2019s name, because, as the 25-year-old enters his prime, having just hit point-per-game territory for the first time in his career with 88 on the season, he\u2019s just getting started in some respects. That having been said, after he became the first Canadiens player to score 50 goals<\/a> (51) since 1990 (Stephane Richer), it will be hard for him to replicate that level of success.<\/p>\n It\u2019s always difficult to hit 50 goals, based on the historical accuracy of that last sentence. If you need further proof to that effect, Caufield trailed only Nathan MacKinnon (53) of the Colorado Avalanche in that department. They were the only two to score 50 this season, and MacKinnon, a perennial Hart Memorial Trophy candidate, had only reached the highwater mark once before in his 13 professional seasons (2023-24). Based on Caufield\u2019s unsustainably high 19.8% shooting percentage, when he has one of 14.2% in his career, he\u2019s more so a candidate to regress here.<\/p>\n Mike Matheson<\/p>\n Defenseman Mike Matheson<\/a> is coming off something of a rebound season after scoring seven goals and 37 points. In 2024-25, he scored six goals and 31 points after hitting a career-high 62 the previous season. Call it the Lane Hutson effect. As the sophomore defenseman has established himself as the team\u2019s premier offensive blue-liner, there\u2019s less ice time in the offensive zone to go around on the back end, especially with the acquisition of Noah Dobson last summer.<\/p>\n So, Matheson, fresh off a $30 million, five-year extension that comes into effect next season, faced having to reinvent himself as a shutdown defenseman instead. He should be commended for doing so, and was with a Bill Masterton Memorial Trophy nomination<\/a>. Results were however mixed. Not only did Matheson not have any business winning that award, which recognizes the player who best exemplifies qualities like perseverance (and obviously didn\u2019t), but the penalty kill, which he was charged with managing game in, game out (with a co-league-leading 3:56 time on ice each contest), ended up with a mediocre 78.1% success rate.<\/p>\n Full voting table for the Bill Masterton Memorial Trophy, won by Avalanche captain Gabriel Landeskog. #GoAvsGo<\/a> #NHLAwards<\/a> <\/p>\n Link to all ballots from @thePHWA<\/a>: https:\/\/t.co\/sW2vfFIfJd<\/a> pic.twitter.com\/VfSTZQnnGk<\/a><\/p>\n \u2014 NHL News (@PuckReportNHL) June 9, 2026<\/a> <\/p>\n That\u2019s not bad per se. However, when it takes away from Matheson\u2019s clear strength as a puck-carrying and moving defenseman, it\u2019s something that should be reconsidered. Chances are it won\u2019t be though, and the now 32-year-old\u2019s offensive production will continue to suffer as time goes on, with him scoring just four points over his last 18 games of the season.<\/p>\n Oliver Kapanen<\/p>\n Life certainly isn\u2019t fair. In a just world, rookie-forward Oliver Kapanen<\/a>, who scored a third-ranked 22 goals in an overwhelmingly successful first full NHL season, deserves more recognition for his accomplishments and respect in general. In reality, he was effectively sat in the playoffs as the warts in his game became apparent (or hit a wall as a rookie, according to the official narrative). Whatever the case may be, amid a constant barrage of reports that the Canadiens will look for a No. 2 centre this offseason to play with Ivan Demidov, who was seen as the primary driver of Kapanen\u2019s success on the second line, the latter will probably slide down the lineup.<\/p>\n I’d be worried if the model said Kapanen was driving his line\u2026 He’s playing his role well enough right now, finishing and filling in blanks. His results away from Demidov are catastrophic, and I don’t know that his 22.5% sh % with Demidov is refelctive of his true talent. https:\/\/t.co\/eYdysLWZX6<\/a> pic.twitter.com\/0BIaEAKOqA<\/a><\/p>\n![\"Cole](\"https:\/\/www.rawchili.com\/nhl\/wp-content\/uploads\/2026\/06\/Cole-Caufield-Canadiens-4-1200x800.jpg\")
Montreal Canadiens forward Cole Caufield \u2013 (Jess Starr<\/a>\/The Hockey Writers)<\/p>\n