Sports fans rarely forget guarantees and boasts that are followed through on. However, they also remember when similar language falls short.

While he was the general manager of the Edmonton Oilers, Sather claimed that he would win the Cup “every year” if he had the Rangers’ budget. After all, he had won five Cups as the coach and GM of the Edmonton Oilers.

In the year 2000 Sather became the general manager and president of the New York Rangers. In his tenure as the big cigar-chomping boss, he reached the Cup Final once, but will leave his role as president without winning a Cup.

At one point that quote was far more widespread before New York Rangers fans had more distractions that demanded their attention: a legitimate superstar in Jaromir Jagr, huge free agent signings, John Tortorella and his prickly relationship with the media, the emergence of Henrik Lundqvist, and numerous big trade deadlines and playoff runs. It got to the point where, by the time Sather stepped back into the shadows and let Jeff Gorton take charge as general manager, you almost forgot that he was there.

Really, there is no black and white response to his tenure. Sather is stepping down from his role as the president of the team with 15 years as the general manager, two different stints behind the bench, three trips to the Eastern Conference Final, one trip to the Stanley Cup Final, and finally four years acting solely as the president without the GM duties. It was truly an era. And now, that era is at an end.

As head coach, Sather went 33-39-11-7 (wins, losses, ties, overtime losses) and missed the playoffs in both stints. Over the course of his 15 years as the general manager, Sather oversaw nine playoff seasons, four head coaches (not including himself), and again, no parades.

That is what most people will remember from the Sather era. Despite all of the big trades, big signings, coaching changes, and a world class goaltender, he didn’t win the Cup in New York — let alone win it every year.

Sather did a lot of very good things for the organization, but it was never enough. He went for it, which in a way should be the norm, but certainly isn’t across the board. While other general managers played it safe, didn’t spend, or couldn’t spend, Sather was the opposite. He was the fighter pilot who was trying to break the sound barrier, and he didn’t care what it cost to do so. The man wasn’t afraid to take risks — to a fault — and never sat back when he thought he had a shot at the Cup.

Towards the end, specifically in his final year as general manager, he threw any caution he had left to the wind to try and grab that illustrious title. As a result, the Rangers lost the 2015 Eastern Conference Final in the first Game 7 loss on home ice in the organization’s long history. Yet again, Sather went “all in” and came away empty-handed.

Sather also represented a buffer to James Dolan, which I believe is often overlooked. Dolan trusted Sather, so much so that he took a step back from being involved with the team — which might be the biggest positive he brought to the team in his tenure.

I often look at Dolan — from a business standpoint — as a pretty good owner. He isn’t afraid to open his checkbook to land a big player or to renovate the Garden. You almost never hear about him being directly involved in business decisions. Sure, he raised ticket prices — yes those prices at MSG are insane — but what owner isn’t doing those things? He wasn’t in the spotlight. He trusted Sather, for whatever reason, and because of that the organization was allowed to operate as a hockey organization without Dolan meddling like he does with the New York Knicks.

It’s fair to say that one of the reasons that Sather held the position for so many years — despite rampant failure early on — was because he had Dolan’s loyalty. He believed in Sather and never saw him as part of the problem. Sather extended this loyalty and stability to the people below him as well, which became an enormous problem.

Tom Renney lasted at least a year and a half too long; it required an all-out team mutiny before the Rangers parted ways with Tortorella; Alain Vigneault lasted three years too long — and Sather wasn’t even the one who fired him.

He let loyalty influence major decisions that ended up damaging the team on and off the ice. He handed out money hand over fist to players including Dan Girardi and Marc Staal, but then refused to re-sign Jagr, never even negotiated with Anton Stralman or Carl Hagelin, and never seemed to mind when the coaching staff didn’t mesh with the higher-up’s view of players (think early Chris Kreider here). Much like everything that has to do with the man, it was a mixed bag.

The problem with going all in is that it’s a double-edged sword. Sather always thought the team was a Martin St. Louis away, until it became clear that they were also a Keith Yandle away. Then they were an Eric Staal away, although that was technically a trade made under Gorton; it felt as if Sather’s fingerprints were all over it. That doesn’t even count the contracts dolled out in free agency, like Brad Richards and further back like Scott Gomez and Chris Drury. And we’re not even talking about the pre-salary cap days when Sather was spending so much of Dolan’s money that you would have thought he was getting a commission on it.

Year in and year out the Rangers were spending, be it in cash or assets, and year in and year out they pushed the bill further down the line. A bill the organization and fanbase has been paying for the past two years, by the way.

When Sather hit on his big bets though, the payoff was typically huge. The Jagr acquisition may go down as one of the best trades of all time. The Scott Gomez trade to Montreal for Ryan McDonagh, Chris Higgins, and Pavel Valentenko is one of the best trades in team history. He hit it out of the park when he lured Kevin Hayes to the organization as an NCAA free agent. Sather also signed Mats Zuccarello after a solid Olympic performance and took a chance Anton Stralman after he was released by the Devils on a PTO. He locked down Marian Gaborik in free agency for less than market value, traded up for Staal — who was a different player before his career-threatening injury — in 2005. And most importantly, he unearthed Lundqvist in the 7th round in the 2000 Draft.

The other side of the coin is, of course, that when he failed, he failed just as big. And Sather failed with all the chips in the middle of the table a lot.

Bobby Holik’s contract was madness from the moment it was inked. He traded Brian Leetch on his birthday without ever speaking to him about it. The Bryan Trottier experiment will forever be remembered as pure insanity. He drafted the only player in the entire 2003 first round to never make an NHL impact in Hugh Jessiman (one note: Jessiman suffered a devastating injury his post-draft year that impacted his career, so this isn’t totally on Sather). He passed on players including Vladimir Tarasenko and Evgeni Kuznetzov to pick Dylan McIlrath at 10th overall in 2010. Sather always believed the team needed enforcers, so he signed Donald Brashear less than a year removed from him delivering a cheap shot and injuring then-fan favorite Blair Betts. In that vein, he gave an enormous “why would you ever offer this” contract to Derek Boogaard, who passed away tragically in 2011.

All of this paints a very strange and complicated picture, which is sort of the point. The Rangers outside of the dark ages were always relevant, even when they missed the playoffs. That hurt them in the long run, since they never bottomed out and always missed out on high-end drafting slots. But the tickets always sold, the team was good enough for national appeal, and the wheel kept spinning.

On one hand stability is good and organizational disruption to front offices can sometimes leak into the product on the ice. On the other, it also inherently breeds stagnation. During times when the organization needed an infusion of new blood or new thinking, they never deviated from their path. Part of that was having the same person man the GM role for a decade and a half, but part of that was also the refusal to move on when the organization clearly should have.

Sather very simply never stepped out of his comfort zone. It was as though Trottier ruined his ability to take risks that wouldn’t immediate be defended by the national pundits who appreciate the old school style of the NHL. After that disaster, his staff hires never rocked the boat, almost all had NYR ties, and rarely came without the approval of the old boy’s club.

Renney was part of the organization as Director of Player Personnel, then Vice President of Player Development before he became the head coach. Tortorella, while a far bigger personality than anyone else hired by Sather, was an assistant for the team and had coached four games as interim head coach with the Rangers in 1999-2000 before winning a Stanley Cup in Tampa Bay. Vigneault had the respect of the old boy’s club going into the gig, and was the right call at the time for a team that needed a win-now coach in 2014.

It wasn’t just behind the bench, though. Gordie Clark was brought into the organization in 2002 and has worked his way up to the role of Director of Player Personnel where he’s remained since. The Rangers have seen enormous grand slams during his tenure, but also some incredible failures that never seem to get more than a passing mention. Jim Schoenfeld has been with the organization since 2005 and seen large promotions over that time. Run down the list of other staff members, and it’s littered with former players such as Leetch, Drury, Adam Graves, Richards, Jeff Beukeboom, Steve Eminger, and Jed Ortmeyer. Most of which, by the way, are very good at what they do, but it does show the organization’s preference for familiarity.

The number of people hired by Sather who were seen as innovators or young up-and-comers was nonexistent. The team has a behind-the-times analytics group, that appears from the outside to be under-funded and ignored. Vigneault used a “sophisticated stats package” no one was allowed to see. Quinn’s use of analytics seems to be more advanced, but we still don’t know how high on the priority pole it is or isn’t.

I will have to come to a bottom line result on this when he is officially gone, but I often wonder just how many reputations Lundqvist saved with his magic. Would we look at Sather differently without Lundqvist? Almost assuredly, since the team would have likely been a disaster for a long, long time and I don’t think Sather ever had the ability to not go for it. And if his draft failures are a part of that reputation, he still deserves the nod for the successes, and Hank was the biggest of the bunch.

As with most things, the answer lies somewhere in between the two extremes. Sather was not the worst general manager in the world, but there’s plenty of evidence that he wasn’t even a good one. His biggest accomplishments were off-ice relationship management that, ultimately, made the team better on the ice. His legacy is complicated in New York, which is fine.

He promised a parade every year. The team came three overtime games short of bringing one home. Now he sits on the board to help find his replacement. They assuredly won’t come into New York with the bravado of “winning a Stanley Cup every year,” but the hope is they oversee one. Because Sather didn’t.

At the end of the day, that’s bottom line.

*Editor’s note. An earlier version of this story stated Anton Stralman was signed out of Europe. This has since been updated, and we regret the error.