Crosby's Superstition, Montembeault's Trade Clock, and the Offseason Stalemates Reshaping October Rosters

Sidney Crosby is eligible to sign a contract extension with Pittsburgh, and the conversation around his next deal has moved beyond whether it gets done—it's about the price tag. Chris Johnston reporting indicates Crosby could command more than his current $8.7 million cap hit in the open market, even at 39 years old. The catch: Crosby is notoriously superstitious, and he's signed at that exact figure for years. The question isn't his market value; it's whether he breaks his own ritual to capture actual raises. This matters for Pittsburgh's salary architecture heading into 2026-27, and it signals whether management believes the window is closing or if they're betting on one more competitive push.

In Montreal, goaltender Sam Montembeault appears positioned as the season's first domino to fall. Frank Serevalli flagged him as the likeliest trade candidate before opening night, a bold call that suggests the Canadiens view him as either redundant depth or expendable in their rebuild. Montembeault's save percentage and goals-against average will be under a microscope in preseason; any dip below his career marks becomes trade-market ammunition for Montreal's front office to move him mid-season at peak value. His workload (starts and backup usage) becomes a leading indicator of where the team's confidence sits.

Kirill Marchenko, Columbus's emerging talent, has gone silent on his future despite his agent Dan Milstein already signaling an exit strategy. Marchenko's refusal to engage the question—deflecting to Don Waddell and the business side—is telling. His agent has already communicated that Marchenko won't re-sign long-term with the Blue Jackets, meaning management is shopping him now or risking a mid-season trade at depressed value. Evgeni Malkin in Pittsburgh compounds the uncertainty; the veteran forward won't commit to playing beyond this season, hinging on how he feels physically. That's a green flag for shedding salary or accelerating a rebuild.

For prop bettors, these situations create operational volatility in the first 30 games. A traded player's line-change history, power-play deployment, and linemate chemistry evaporate overnight. Montembeault's workload and Marchenko's ice time are not stable inputs for prop modeling; if either moves mid-November, any season-long projection built on their early-October usage becomes obsolete. Crosby's contract stance is less relevant to props (he's playing full minutes regardless), but Malkin's day-to-day fitness questions his availability for props targeting Pittsburgh forward production. Pittsburgh's forward group totals, assists leaders, and team power-play point accumulation all carry elevated uncertainty until Malkin clarifies his status and the Crosby extension settles.

The preseason games begin September 19th (already underway), and regular season opening night arrives September 29th, giving bettors less than two weeks to source clarity on Montembeault's role, Marchenko's trade status, and Malkin's availability. Any early season lines assuming baseline usage for these three players risk obsolescence.