Look at the names and look at the trades.

There’s almost no way to win when a NHL general manager decides to deal his captain –especially in situations like the one Jay Feaster found himself in with Jarome Iginla.

You simply can’t replace the heart and soul of the franchise in one fell swoop. Five first-round picks from the Pittsburgh Penguins wouldn’t have even guaranteed good value for Iginla, although it obviously would have been a good bet to.

The point is when a player means as much to a franchise as Iginla did to the Flames. it will likely take years to fill the massive hole he leaves behind.

Hockey Central Trade Tracker | #Iginla, #Flames trending

Even if college prospects Kenneth Agostino and Ben Hanowski turn out to be solid NHL players (no sure bet) and the Flames draft another quality prospect with the Penguins’ first-round pick, the haul probably won’t look like enough years down the road.

No one was more aware of that than Feaster, who found himself in an unenviable position as the triggerman on this transaction.

“I told Jarome, I said `This is not why I came to Calgary, to be the guy that traded Jarome Iginla,” Feaster said Thursday. “I came because I wanted to win a (Stanley) Cup with Darryl (Sutter) as GM and Jarome as the captain. It’s an unfortunate and difficult part of this business.”

How do you go about trying to replace the franchise leader in goals, points and games?

Even if the player is in the twilight of his career — as Iginla certainly is — it’s not easily done. That helps explain why it is pretty rare to see a captain traded away.

Ray Bourque once became Brian Rolston, Martin Grenier, Samuel Pahlsson and Martin Samuelsson — and later returned to Boston for a summer celebration with the Stanley Cup. Another Bruins captain, Joe Thornton, was flipped for Brad Stuart, Marco Sturm and Wayne Primeau.

At the height of his career, not long after leading the Edmonton Oilers to a fifth championship, Mark Messier was dealt for Bernie Nicholls, Steven Rice and Louie DeBrusk.

And let’s not get started on Wayne Gretzky, who was involved in two no-win transactions during his legendary career.

Among the names going the other way in those deals out of Edmonton and Los Angeles?

Jimmy Carson, Craig Johnson, Patrice Tardif, Roman Vopat, Martin Rucinsky, Nick Stajduhar, Peter Hogan and Matt Zultek.

You get the picture.

The Iginla situation was very similar to what Mats Sundin went through with the Toronto Maple Leafs at the trade deadline in 2008 — only with a different outcome.

Back then, Sundin refused to waive his no-trade clause because he felt like it would be akin to “giving up” on the team he had captained for so long.

Some fans in Toronto still haven’t forgiven him for it.

Years later, Sundin acknowledged the parallels to Iginla’s dealings with the Flames now and detailed the delicate dance for ownership, management and the player himself.

“It’s a challenge, no matter (how) you’re involved,” Sundin told sportsnet.ca Wednesday. “Whether you’re an organization or a coach or a player it is tough. … You just wish that everything goes down well and all parties are happy.”

In reality, that’s not likely to happen.

Happiness for Iginla will obviously come from a winning a Stanley Cup.

In Pittsburgh, the veteran winger will be reunited with Canadian Olympic teammates Sidney Crosby and Brenden Morrow, who had been the Dallas Stars captain until being acquired by the Penguins last weekend.

The Flames will set about moving forward by dealing away more players before Wednesday’s deadline in what is likely to be a rebuild in everything but name.

The one unanswerable question is whether the Flames could have got significantly more back for Iginla a year or two ago, when calls for the organization to part ways with the captain first surfaced.

History shows us it probably wouldn’t have made that much of a difference.

It was only in recent weeks when Feaster decided the time had finally come to trade Iginla — something many thought would never happen after 16-plus years with the Flames.

“I approached Jarome and had a number of conversations with him about where we are and what our thinking is going forward and asked him to submit to us a list of teams where he would be willing to go,” explained Feaster. “He did that and we started discussions with the teams that were on the list that he provided.

“We began negotiations with teams and in the final analysis we had offers from three different clubs.”

They had to find a way to make it work with the Penguins. Iginla essentially had control of the process because of the no-movement clause in his contract, and it’s pretty clear that he wanted to pursue a championship in The Steel City.

Feaster obliged.

The deal might not look very impressive on paper, but truth be told that was always going to be the case.

A look back at some notable trades involving captains:

Wayne Gretzky (Edmonton) — Aug. 9, 1988

Gretzky traded to Los Angeles by Edmonton with Mike Krushelnyski and Marty McSorley for Jimmy Carson, Martin Gelinas, a first-round pick (later traded to N.J.) in 1989 draft, a first-round pick (Martin Rucinsky) in 1991 draft and a first-round pick (Nick Stajduhar) in 1993 draft, plus $15-million in cash.

Mark Messier (Edmonton) — Oct. 4, 1991

Messier traded to N.Y. Rangers by Edmonton for Bernie Nicholls, Steven Rice and Louie DeBrusk.

Ron Francis (Hartford) — March 4, 1991

Francis traded to Pittsburgh by Hartford with Grant Jennings and Ulf Samuelsson for John Cullen, Jeff Parker and Zarley Zalapski.

Wayne Gretzky (Los Angeles) — Feb. 27, 1996

Gretzky traded to St. Louis by Los Angeles for Craig Johnson, Patrice Tardif, Roman Vopat, a fifth-round pick (Peter Hogan) in 1996 draft and a first-round pick (Matt Zultek) in 1997 draft.

Ray Bourque (Boston) — March 6, 2000

Bourque traded to Colorado by Boston with Dave Andreychuk for Brian Rolston, Martin Grenier, Samuel Pahlsson and a first-round pick (previously acquired from N.J., Boston selected Martin Samuelsson) in 2000 draft.

Jaromir Jagr (Pittsburgh) — July 11, 2001

Jagr traded to Washington by Pittsburgh with Frantisek Kucera for Kris Beech, Michal Sivek, Ross Lupaschuk and future considerations.

Joe Thornton (Boston) — Nov. 30, 2005

Thornton traded to San Jose by Boston for Brad Stuart, Marco Sturm and Wayne Primeau.

Ryan Smyth (Edmonton) — Feb. 27, 2007

Smyth traded to N.Y. Islanders by Edmonton for Ryan O’Marra, Robert Nilsson and first-round pick (Alex Plante) in 2007 draft.

Mike Richards (Philadelphia) — June 23, 2011

Richards traded to Los Angeles by Philadelphia with the rights to Rob Bordson for Brayden Schenn, Wayne Simmonds and a second-round pick (later traded to Dallas) in 2012.