Yesterday’s report that the Rangers intend to buy out the final year of Chris Drury’s contract signals the end of yet another Glen Sather mistake – something that is becoming a regular occurrence in New York.For the past decade, Glen Sather has essentially dug a hole in the ground and thrown millions and millions of dollars into it. If there was an aging superstar entering free agency you could be sure that Sather was the most persistent suitor for their service. Even if there wasn't a superstar available, Sather would pay someone as if they were a superstar.Now the hot rumour is that the Rangers are going to fall over themselves trying to sign Brad Richards to a lucrative contract. It almost seems unfair that a team can give someone a $7 million contract seemingly every season and wiggle out of these commitments when it becomes apparent they made a terrible mistake. ().What’s confusing is that aside from spending money, Glen Sather is an adept GM.Sather has shown an ability to acquire superstars for close to nothing. He brought in Pavel Bure for two prospects and three draft picks that accumulated a mere 33 games in the NHL; Eric Lindros for Kim Johnsson and spare parts; and Jaromir Jagr for Anson Carter.Injuries curtailed Bure's time in New York, but he scored 50 points in 51 games. Lindros suffered a similar fate, but still gave the Rangers a 70+ point season and a 50+ point one. Jagr was the true steal, scoring 123 points his first season (the 3rd best total of his career), 96 in his second, and 71 in his third. In total, Sather brought in close to 500 points for a bag of rocks.Sather has also finally started building a solid young core of players that includes Brandon Dubinsky, Ryan Callahan, Marc Staal, Derek Stepan, and others.Plus, he seems to find takers for some pretty unattractive contracts (which we’ll discuss in more detail later).This is also a man inducted into the Hockey Hall of Fame. He’s clearly great when given all-world talent to work with. He won four Stanley Cups with the Oilers in the 1980s and played a major role in building team Canada for the 1984 Canada Cup, 1994 World Hockey Championship, and the 1996 World Cup of Hockey.However, his Hall of Fame induction was in 1997, three years before he became this free spending maniac GM.Enough with the pleasantries; you’re reading this for a juicy trash session. Here are the (current) worst moves of the Glen Sather Era. Remember, as long as Sather has money to spend as the Rangers’ GM, this list is a work in progress.Yes, the first signing isn’t actually a player, but a coach. Sather signed Trottier as head coach in 2002, despite having no experience as a head coach (because starting your head coaching career in a market like New York is always a brilliant idea). New York fans hated Trottier and he lasted only 54 games of sub-.500 hockey before being fired.Sather signed Donald Brashear to a two-year, $2.8 million deal, which is peanuts compared to some of the other players on this list, but that’s a lot of money for someone who can’t actually play hockey. Brashear’s signing went over about as well as a fart in church. He received boos at the season ticket holders’ meet-and-greet for laying a brutal cheap shot on Blair Betts during the playoffs a year before. Brashear was eventually put on waivers before completing his first season in New York (foreshadowing alert).Instead of learning that enforcers aren’t the best players to overpay, Sather signed Derek Boogaard to an astonishing four-year deal worth $6.5 million. Boogaard suffered a concussion during a fight with Matt Carkner late in 2010 and did not play another game for the Rangers. Unfortunately, Boogaard passed away last month after accidentally mixing alcohol and oxycodone.In 2002, Sather gave the 30-year-old Kasparaitis a six-year, $27 million deal. In his first season in New York, Kasparaitis played 80 games and was a +5, but logged less than 20 minutes a night. This was the high-point of his New York career.The next three seasons were filled with injuries and ineffectiveness. The Rangers waived Kasparaitis twice in 2007 and eventually loaned him to SKA St. Petersburg of the Russian Superleague.Rozsival signed with the Rangers after the lockout and produced three productive seasons with the blueshirts, accumulating over 100 points and quarterbacking the Rangers’ power-play. Of course that warranted a new four-year, $20 million contract.Rozsival was given $5 million per season despite never breaking 50 points in a season or being regarded as an overly defensive presence on the blueline.Rozsival eventually became a whipping boy in New York as his point totals declined and he struggled living up to the weighty expectations of his over-inflated contract.But, in true Satherian fashion, the Rangers’ GM made his mistake disappear by shipping him off to Phoenix for Wojtek Wolski, who is also a rumoured buy-out candidate.Amazingly, this contract was probably based on the most historical production, but it was still a gross overpayment. Scott Gomez actually scored over 80 points in one season, that being the first season after the lockout. The next season, Gomez produced a reasonable 60 points for the Devils before becoming an unrestricted free agent.Sather called.The Rangers’ GM offered Gomez a hefty seven-year, $51.5 million contract. Currently, that $7.35+ million cap hit is the 11th highest in the league. This for someone whose track record for great performance included a single season. Of course, Gomez did bring valuable Stanley Cup experience, but this can hardly account for the extra millions he received.In the first year of the mega-deal, Gomez scored 70 points, tying his 2nd highest career point total. This still felt like a disappointment considering he was making elite money and was outside the top-30 in scoring. Gomez’s totals declined the following year and it was clear the contract was a mistake.The red flag was that Gomez’s huge 80-point season was the first season after the lockout. Scoring jumped for certain players who were small and quick because the league was still filled with many older, slower players who just couldn’t keep up physically. Plus, the amount of power-plays that first year was ridiculous. Expecting Gomez to replicate this season was unrealistic.This is no longer Sather’s problem as he parlayed Gomez and his anchor of a contract into Ryan McDonagh in a trade with the Montreal Canadiens. I still don’t understand how a team gives up assets in a salary dump trade, but Bob Gainey is in the Hall of Fame; I'm not.Drury signed with the Rangers on the same day as Scott Gomez, which created ripples throughout the league. "Wow, they got both of them... Wow, they're paying them how much!?"Drury was coming off two 30+ goal seasons with the Buffalo Sabres, who were taking full advantage of the first few years after the lockout and were looking like a dynasty in the making (never panned out).Drury’s red flag was that he was over 30 and never broke 70 points in his career.That didn’t stop Sather from paying him like he was 25 and scoring 80+ points. Drury signed a five-year, $35.25 million contract, which put his cap hit at just a touch over $7 million.The Rangers were paying Drury to play like an elite scorer, even though he was better suited for a strong two-way role that could produce in the 60 point range. That’s a good player (like many on this list were), but not for the money he was then making.Drury never again broke 25 goals or 60 points and only scored five points in 24 games this past season.This is another example of a productive player miscast in New York and left to struggle under the weight of a contract they should have never been offered.This signing represents everything that was wrong with the old NHL. Holik was a pretty effective two-way centre during his stay in New Jersey. However, he never scored more than 30 goals and topped out at 65 points.Sather didn’t care: he signed the 32-year-old to an obscene five-year, $45 million contract. Yes, that’s right; at one point Bobby Holik was earning $9 million a season. That really blows my mind. Holik scored 91 points for the Rangers… over two seasons before having his contract bought out (notice the trend here).I’m so happy Sather went nuts here because the Leafs were going just as hard after Holik. Money makes people do crazy things.I feel bad for Wade Redden. It isn’t his fault the Rangers came calling with a huge contract offer two years after he was capable of playing strong, two-way hockey.The Rangers gave Redden a six-year, $39 million contract, despite Redden’s career ceiling of 50 points and two most recent years of sub-40 points. Those previous two seasons also represented two of Redden’s lower +/- campaigns. This statistical dip suspiciously coincided with Zdeno Chara’s departure. Could Chara actually be covering up for Redden’s mediocre defensive play? Sather decided to spend $6.5 million to find out.Like almost everyone else on this list, the Rangers waived Redden before the start of the 2010-2011 season and he now spends his time playing hockey in the AHL.You don’t blame a dog for eating his whole sack of food and subsequently barfing all over the place: you blame the owner. Likewise, you don’t blame these athletes for signing lucrative contracts they can never justify: you blame Glen Sather.For everyone counting at home, here’s how well Sather spent the Rangers’ money.39 years$227.05 millionWithout including Brashear and Boogaard, the average contract Sather gave out averaged 5.5 seasons and was worth almost $6.6 million per. The average amount of games these players lasted in New York was less than two and a half seasons and resulted in approximately 53 points a season for the forwards and nearly 21 points for the defencemen. Not a very good return on your investment.Just remember: Sather managed to escape every single one of these contracts and has another $7 million plus to spend this off-season. Here we go again.