Don't want to start a new thread for this question so I'm bumping this one.
The way Ovechkin breaks the record is important right? Right now he's playing well, on pace to score +50 goals and break the record this year. The Capitals are a good team, in a playoff position.
Breaking the record this way, adds far more to his legacy than if were playing poorly, scoring 20-30 goals a year while being a liability on a bottom feeder?
It won't matter to casual fans. But for me, it's important. Here's an
old post where I talk about how the circumstances matter:
1. If Ovechkin gets the all-time record for goals, regardless of how he gets there (see point #3), absolutely it will influence his legacy among casual fans. Most hockey fans don't do deep analysis, so holding a significant all-time record will boost his legacy. (In fifty years, Ovechkin's one-sentence summary could be something like "all-time leader in goals scored, won three Hart trophies, won an Art Ross and Conn Smythe, big hitter, greatest or 2nd greatest LW in NHL history").
2. Regardless of whether Ovechkin gets to #895, I don't think it changes much about his career (beyond superficial bullet points). Career totals have always been a poor way to evaluate a player. Besides, Ovechkin has
already surpassed Gretzky by any reasonable measure of era-adjusted goals.
Weztex and bobholly39 cover this well in their posts. If you don't already have Ovechkin ranked as the greatest goal-scorer all-time when he's at 880-something goals, whether he gets another ten goals beyond that is superficial and arbitrary. To make an analogy - I've seen people say that Peter Bondra didn't deserve to be in the Hall of Fame after 2006 (when he was at 498 goals), but he magically became a HOF'er in 2007 (when he was terrible but scored five more goals). This "line in the sand" type of thinking is completely arbitrary and emphasizes numbers for the sake of numbers. (Stats can be the byproduct of playing well, but they're not the end goal in and of themselves).
3. That being said, it would also depend on how Ovechkin reaches #895. If he scores, say, 45, 40 and 35 goals in consecutive seasons (always playing at a high level), that would make his career more impressive because instead of having a 17 year prime, that means that he'd have a 20 year prime. Very few players have performed as well as Ovechkin in his mid 30's, and if he plays at an all-star level for three more years, he's getting into Gordie Howe and Ray Bourque territory.
On the other hand, if Ovechkin suddenly begins struggling and hangs on for six years as a powerplay specialist (otherwise relegated to the third-line ), and gets 20 goals per year this way, that adds nothing to his legacy. (This is how Dave Andreychuk reached 600 goals). If Ovechkin scores 40-45 goals for two years and retires with ~860 goals, I'd find that more impressive than if he reaches 895 goals, playing six years as a geriatric Dave Andreychuk clone. What counts is the level of performance.
4. I don't think much changes for Gretzky if Ovechkin reaches #895. For the superficial fans (who are looking for bullet points, rather than any deep analysis) - Gretzky still has another 60 records, so he'll be fine. For those doing a deeper dive - a lot of regulars on the History forum (myself included) already don't consider Gretzky the greatest goal-scorer in NHL history (so it's not like he's losing the top spot in this category). Ovechkin will continue to climb the all-time rankings if he continues to play at an all-star level, of course, but what counts is his level of performance (rather than the career totals for the sake of career totals).