The days leading up to Monday’s NHL trade deadline have produced a rash of deals that have drawn a clear line in the sand between the franchises going all-in at the deadline in the hopes of a Stanley Cup and those only interested in adding a few small pieces.

The perennial Cup favourite Chicago Blackhawks made the most brazen deal of trading season on Friday night, snagging two-time Stanley Cup winner Andrew Ladd. Ladd was one of the most coveted players available and there were groans throughout the hockey world about the rich getting richer. But Blackhawks general manager Stan Bowman wasn’t finished, quickly adding depth forwards Dale Weise and Tomas Fleischmann from the Montreal Canadiens. Bowman also ensured the Canadiens retained 30% of Weise’s salary and the Jets retain 36% of Ladd’s salary, partly because the Blackhawks are up against the salary cap but also because if you’re going to order dessert, why not add some whipped cream on top?

You can’t fault the Blackhawks for moving for a player of Ladd’s quality. But trades made against a deadline being the dubious moves they are, you have to wonder if this one is actually going to pay dividends in the end.

Every season a handful of teams go all-in at the deadline, making large acquisitions with varying results. The Blackhawks appear keen on bucking their deadline fortunes from last season when they snagged one of the most highly touted available players in the days leading up to the deadline, Antoine Vermette from the Arizona Coyotes. Vermette took a while to find his game and didn’t exactly thrive with the Hawks: he had 1.4 even-strength points per 60 minutes with the Coyotes in 2014-15 before the trade. With the Hawks for the duration of the season including the playoffs, that number fell to 1.1 according to War on Ice. Vermette went from being depended on to be an offensive weapon in Arizona but had difficulty transitioning to a support role in Chicago.

The Blackhawks ended up winning the Stanley Cup so you could argue it’s a moot point. Still, they gave up a first-round pick for Vermette, as they did with Ladd. Despite their win now mentality, flipping future draft picks for players on the wrong side of 30 is a move that could come back to haunt them.

Going back the 10 seasons since the 2004-05 NHL lockout, adding aging veterans with unquantifiable intangibles to benefit the locker room was another trend for eventual Stanley Cup champs. In 2006 the Carolina Hurricanes added 37-year old Mark Recchi at the trade deadline. His 16 points through 25 playoff games was impressive and for a team that featured seven of their top 10 playoff scorers over the age of 32, it seemed perfectly in line with their modus operandi.

The 2009 Pittsburgh Penguins had an alarmingly young core and added 38-year old former Cup champion Bill Guerin to the mix. His 15 points through 24 playoff games was third in team scoring but it was his voice in the room that likely made the biggest difference for Sidney Crosby and the Penguins in their only Stanley Cup since 1992. “You don’t need a letter on your jersey to be a leader,” he told ESPN.com after their Cup win.

The results aren’t always as noticeable. In 2011, the eventual Cup champion Boston Bruins added 32-year old defenseman Tomas Kaberle at the deadline in a deal that most certainly did not put them over the edge. Kaberle managed just 11 points through 25 playoff games and left the Bruins the next season. His average time on ice during the playoffs was a measly 16:02, fifth among Bruins defenseman and he was largely inconsequential. He’d gone eight seasons out of the NHL playoffs and struggled to keep up with the grind of four playoff series. One of the draft picks the Bruins traded for Kaberle turned into scoring center Richard Rakell, who would be a nice addition to their playoff push right now.

The New York Rangers are experts when it comes to big players who fizzle out. They paid a hefty price (Including young scoring winger Anthony Duclair and a first-round pick in this year’s draft) for two-time All-Star puck-moving defenseman Keith Yandle at last season’s deadline and were bounced in seven games in the Conference Finals. Yandle is now rumoured to be on the move again. The previous season, the Rangers pulled a stunner with a late deal, acquiring 38-year old former Hart and Art Ross trophy winner Martin St Louis from the Tampa Bay Lightning for what would turn into two first-round picks. While the Rangers would indeed make it to the Cup final, these two picks would turn into two bona fide scoring forward prospects: Joshua Ho-Sang and Anthony Beauvillier. St Louis turned into a leader on the Rangers and, had they won the Cup, would have been viewed as the ultimate deadline acquisition. Yandle’s offensive abilities generally override his defensive shortcomings (not unlike many puck-moving defensemen). He’s the type of player necessary for a deep playoff run but the obscene price the Rangers paid for him have in turn created more trade rumours as they seek to get value back instead of losing him to free agency.

On Sunday the Rangers made another risky play for a big name, acquiring 31-year old pending UFA Eric Staal from the Carolina Hurricanes for second-round picks in 2016 and 2017 and blossoming Finnish prospect Aleksi Saarela. The aging Rangers now own just five picks in the upcoming draft. Staal still has some scoring prowess left in the tank and can drive possession well but it’s tough to imagine him re-signing in New York. For a team that has a severely depleted prospect pool and now Stanley Cups to show for their efforts, these are deals the Rangers may live to regret.

Now, the Blackhawks seem confident enough in their roster to make another Cup push. But this was a roster that, before their two deals, was already second in the Central Division, the toughest in the NHL. If it doesn’t happen for the Hawks this season and either Ladd, Fleischmann or Weise underperform, the hockey world will keep a keener eye on how the prospects and draft picks they flipped play out.

A late challenger for the Hawks deadline supremacy emerged on Saturday: the upstart Florida Panthers, who traded four draft picks spread over three years for three depth players including Teddy Purcell, Jiri Hudler and Jakub Kindl. After finishing sixth in the Atlantic Division last season the Panthers have surprised the entire league and defied their poor underlying statistics to stay on top of the division this season. Their work on Saturday is nearly as brazen as the Hawks and Panthers GM Dale Tallon said after the deals that Panthers ownership has given him “Carte blanche” to “Go out and get it done.” The Panthers are clearly dreaming big.

“Who says we’re done?” Tallon added, implying they might not be finished making moves.

Of course, both the Panthers and the Blackhawks cannot take home Lord Stanley’s mug this summer, so there is the strong possibility that one, or perhaps both teams, could live to regret these deals.

Another school of thought is that making deadline deals is a sign of faith from management to the team that they’re serious about winning and it instills a hit of confidence in the lineup. The Blackhawks and Panthers moves will inevitably put pressure on the Washington Capitals and the Dallas Stars, two of the other elite teams in the league, to bolster their rosters before Monday’s deadline. There are players available, but as the hours before the 3pm deadline wither away, the asking prices get larger and the risk invariably rises.