But this time they nailed it.
This time they finally did what was best for both parties involved.
After seven frustrating years for both the player and the organization, the Flames traded the 24-year-old forward and a sixth-round pick in 2022 to Florida on Monday for a second-round pick in 2022 and prospect Emil Heineman.
Brad Treliving didn’t so much cut bait on the highest draft pick in team history as he cashed in on a playoff reputation that garnered his club a significant haul for an increasingly disappointing player.
As he said about the Bennett deal, and the one that sent David Rittich to Toronto for a third-rounder a night earlier, “these moves weren't going to be available to us beyond today.”
So Treliving made the most of Florida’s desire to add depth via the proven playoff snarl Bennett built his reputation around.
The combination of being mismanaged at times and underperforming most others, the man picked fourth overall in 2014 gets a new chance to start proving he deserved better in Calgary.
“I think if you could do things over in life… it could've been handled a little bit differently,” said a philosophical Treliving after having a long discussion with Bennett earlier in the day.
“I don't put that on Sam. I think at the end of the day, Sam worked hard here. That was never an issue. We've got a good relationship with Sam. We think a lot of the young man. But I think he's going to embrace a fresh start and we wish him all the best.”
Keeping Bennett past Monday’s deadline would have meant either losing him to Seattle in the expansion draft or having to qualify him with a raise on the $2.55 million contract he’s played under for two years, while scoring just 12 goals.
In that time, he dealt with three of the five different coaches who toyed at times with giving Bennett a top-six role he was never able to make good on.
While toiling largely on the third and fourth lines, Bennett still saw himself as someone capable of taking on a bigger role – a vision the organization didn’t share.
It was only in the playoffs the kid who scored 18 goals as a rookie seemed able to reach his potential.
It was then he doubled his regular season points per game from .34 to .63 and was amongst the Flames’ best players in each of the four playoff series he participated in as a Flame.
It all left everyone wondering how a man capable of elevating his emotional, physical and offensive game each spring, could return to being so inconsequential each fall.
"I don’t know exactly the reason – I think I definitely got moved around a lot," said Bennet Monday when asked why things didn't unfold the way he envisioned in Calgary.
"Seemed like I got more opportunity in the playoffs than the regular season and I excelled in that. For whatever reason, it just didn’t click. That happens sometimes. We (he and Treliving) just talked it over and it’s definitely a little sad. I really enjoyed my time in Calgary. I loved my teammates, the city and the fans. I definitely enjoyed all of that."
Bennett figured it always had plenty to do with opportunity, which led to his trade request earlier this year.
The Flames were perfectly content to ignore the request from the RFA, but when the club’s playoff chances were all but officially erased the last few weeks it opened the door for a windfall they never could have received any other time.
And the beauty is that the return doesn’t require protection in the expansion draft.
"At the end of the day you're going to lose a player, you can't get around it,” said Treliving, who would have exposed Bennett.
“We felt this made sense on a couple of different levels other than just the return we got on the player. For both him and David, we've got a job to do. None of this should be perceived as us throwing in the towel. We had to make some decisions on players whose contracts were expiring. We had expansion issues. We felt we got a real good return.”
Sure did, for a fourth-liner and backup goalie.
Heineman was a second-round pick of the Florida Panthers in 2020 and has spent the last two seasons with Leksands IF where the right winger has played 54 games, scoring seven goals and adding eight assists for 15 points. He represented Sweden at the 2021 IIHF World Junior Hockey Championship.
Keep in mind, Treliving acquired a second-round pick for Sven Baertschi and for Kris Russell in 2015 and 2016 respectively, turning them into core pieces Rasmus Andersson and Dillon Dube.
Valuable picks indeed.
"The draft capital doesn't mean a lot right now, but I think it's going to become much more valuable with each day that goes by and as we get into the summer with the pending expansion draft, I think those picks are going to become much more valuable,” said Treliving, who said a recent chat with Rittich’s agent made it clear the signing of Jacob Markstrom last fall meant Rittich would sign elsewhere next year.
“I think it's fair to say that come year-end he was probably going to look for a fresh start, which is fair. You balance that and say 'okay you're going to have a player that more than likely is going to walk at the end of the year, what does the market say?'”
It said, “cash in,” which is exactly what Treliving did.
"There have been lots of ups and lots of downs,” said Treliving of the path Bennett’s career has taken since the GM drafted him a month after being hired in Calgary.
“It hasn't gone perfect.”
But Monday’s move was close.