Friends, the NHL Draft is one of the most fun weekends of the year. Not only does it represent the fulfillment of lifelong dreams for a couple hundred young hockey players, but it’s also a time where the league’s 32 general managers tend to make big trades.

The Calgary Flames have made a lot of trades during the weekend of the NHL Draft – the two days of the draft and the day before – but not all of those trades were gems.

Here’s a chronological rundown of five draft weekend trades that haven’t aged well.

1990: Joe Mullen to Pittsburgh for 1990 second-round pick

The Flames were a year removed from their Stanley Cup win in 1989, and the Flames were upset in the first round of the playoffs by the Los Angeles Kings, losing in six games. The loss led to some introspection from general manager Cliff Fletcher and some changes, as he aimed to revamp the roster to add some youth.

One of the first players on the chopping block in the transition was 33-year-old Joe Mullen, whose offensive production dropped from 51 goals and 110 points in 1988-89 to 36 goals and 69 points in 1989-90. You could argue that the Flames sold low on Mullen, and received a second-round pick that they used to select Nicolas Perreault.

The “aging” Mullen played for seven more years and won two Stanley Cups with Pittsburgh. Perreault never played a single NHL game.

Also 1990: Brad McCrimmon to Detroit for 1990 second-round pick

Nicknamed “Beast” for his intimidating nature on the ice, McCrimmon was the Flames’ captain in 1989-90 and seemingly bore the brunt of the team’s first-round disappointment, as he was shipped off to Detroit for a second-rounder.

The Flames used that second-rounder, 24th overall, to trade up in the first round to select Trevor Kidd. New Jersey used the Flames first-rounder to select obscure QMJHL netminder Martin Brodeur. Wonder what happened to him…

1994: Mike Vernon to Detroit for Steve Chiasson

This one at least made some sense on paper.

Mike Vernon had just turned 31 and had battled a recurring back issue. Trevor Kidd was younger and, with Vernon nearing the end of his contract, likely to be a much less expensive option. So after spending the 1993-94 season as Vernon’s backup, the Flames went all-in on Kidd and sent Vernon to Detroit for veteran blueliner Steve Chiasson. (Vernon’s run with the Flames ended with him as the goalie of record as the club blew a 3-1 series lead in a first-round loss to Vancouver. The Flames were concurrently making moves to revamp their blueline, and Chiasson sort of fit in there, too.)

Kidd didn’t end up being what the Flames hoped, posting a below .500 record in two of three seasons as starter before being traded to Carolina. Vernon back-stopped the Red Wings to two Stanley Cup Finals, including a Cup win in 1997 that saw Vernon named the Conn Smythe Trophy winner as playoff MVP.

2011: Robyn Regehr, Ales Kotalik and 2012 second-round pick to Buffalo for Chris Butler and Paul Byron

By 2011, the Flames had missed the playoffs in each of their past two season and were seven years removed from their 2004 run to the Stanley Cup Final. They entered the 2011 draft with general manager Jay Feaster trying to solve some problems: primarily getting out from under a cap crunch and to figure out a way to retain pending free agent Alex Tanguay.

Shutdown ace Robyn Regehr was 31, carried a $5 million cap hit and starting to show signs that his physical style was wearing him down. Ales Kotalik, acquired in one of the ill-fated Olli Jokinen trades (there were a couple), carried a $3 million cap hit and wasn’t really an NHLer anymore. So the Flames packaged the duo along with a second-round pick as a sweetener and sent them to Buffalo in exchange for a depth defender (Chris Butler) and a depth forward (Paul Byron).

The same day, the Flames used the freed-up cap space to sign Tanguay to a new contract. Feaster was able to keep the band together, so to speak, but the Flames missed the playoffs in the next two seasons and embarked upon a rebuild in 2013. Regehr played for another four seasons, winning a Stanley Cup in 2014.

2017: 2018 first-round pick, 2018 second-round pick and 2019 second-round pick to NY Islanders for Travis Hamonic and 2019 fourth-round pick

In 2015, the Flames made a big splash at the draft, packaging their first-round pick and two second-rounders to Boston in exchange for young blueliner Dougie Hamilton, fresh off his entry-level deal. Hamilton needed a new contract, sure, but he was entering his prime and the Flames bet on that.

Two years later, the Flames packaged their first-round pick and two second-rounders to the New York Islanders for veteran shutdown blueliner Travis Hamonic. On one hand, Hamonic was already under contract, and offered a physical, defence-first style that the Flames didn’t have. On the other hand, this was a definite, significant overpay for what Hamonic provided.

Food for thought: in the two seasons after the Flames acquired him, Hamonic registered 30 points and the club had a minus-34 all-situations goal differential with him on the ice. In the two seasons after the Flames acquired Hamilton, he registered 93 points and the club had a plus-34 all-situations goal differential with him on the ice. They had the same acquisition cost.