By Tuesday night, GMs had spent nearly $500 million on UFAs. As always, a ton of that money was spent recklessly and was used to sign future buyouts. Amidst the chaos there were some reasonable deals and some outright steals.

Here's a recap of some of the worst and best contracts handed out on the first day of free agency.

Worst contracts

Deryk Engelland 3 years, $8.7 million

The Flames were having a pretty good day after nabbing both Jonas Hiller and Mason Raymond for relatively short deals worth wholly appropriate dollars. Then everything went to hell when they gave Engelland the Jeff Finger treatment. Engelland has averaged only 14 minutes a night over his career, so that's nearly $3 million a season for a No. 6 defenceman at best.

Dave Bolland 5 years, $27.5 million

Anytime you can add an injury-prone third-line centre who has never cracked 50 points in a season and is coming off a devastating ankle injury, you have to do it. Especially when it costs you top-6 money. This is a disastrous contract, one the Leafs should be joyous they didn't match. Bolland was replaced as the second-line centre in Chicago by Michal Handzus of all people and he isn't any younger, healthier, or with better linemates than he was then.

Brooks Orpik 5 years, $27.5 million

Soon to be 34, Orpik's best days are well behind him. He's been declining for a number of years and his defensive ability is nothing more than a reputation at this point. That didn't stop the Capitals from committing way too many years and way too much money.

Leo Komarov 4 years, $11.8 million

By acquiring Matt Frattin and signing Komorov, it looks like Dave Nonis is trying to get the band back together (except not the good players he let go). Komorov fills the pest role nicely, but he's offense was pretty non-existent in Toronto (9 points in 42 games), despite spending the majority of his time with Nazem Kadri, Mikhail Grabovski, or Clarke MacArthur. You don't pay guys who can't score that much money. For a comparable price over fewer years the Leafs whiffed by letting Raymond walk to make room for Komorov.

Best contracts

Christian Ehrhoff 1 year, $4 million

A good deal for both team and player. Ehrhoff gets a chance to win and can rebuild some major value by quarterbacking a power play that features some serious firepower. Going back to market next year after a 40-50 point campaign means big money, even if Ehrhoff is 33 by then (just look at Orpik). Pittsburgh gets a top-4 defenceman at a bargain price.

Anton Stralman 5 years, $22.5 million

Next to Ryan McDonagh, Stralman has been the Rangers best defenceman for the past two years. Choosing to re-sign Dan Girardi over Stralman is going to one of Sather's biggest mistakes of this off-season. Stralman hasn't put up many points in recent years in large part because he hasn't been used very much on the power play. What he has done is drive play remarkably well. In years past that hasn't commanded big dollars on the free agent market, and although more teams are using analytics, the Lightning were still able to get themselves a top 4 defenceman for less than what a lot of teams spent on worse players.

Tom Gilbert 2 years, $5.6 million

How many top-pairing defenceman can you sign for less than $3 million a season? Not many, but the Canadiens found themselves one. You can argue that Gilbert is a product of Brian Campbell—despite Gilbert's history of making his team better when he's on the ice—but he could get to play with PK Subban in Montreal, which is like an even better Campbell. Gilbert worked out astoundingly well for Florida and he will work out just as well for Montreal.

Mark Fayne 4 years, $14 million

Another top-pairing defenceman who went cheap. Fayne played shutdown minutes for the Devils, and although Peter DeBoer's low-event system may have inflated Fayne's possession numbers, it's pretty rare for a guy getting tough minutes to see his team do better when he's on the ice. He's young enough and a good enough puck mover that the Oilers are still getting Fayne's prime and can let another team take his decline four years down the road.