Ask any Leafs fan of any age and they’ll be able to tell you about some kind of big trade that ended up in disaster. Rask for Raycroft, the Toskala trade, trading away the pick that ended up being Scott Niedermayer. There have been some bad ones.

A recurring theme when I talk to Leafs fans is all the “win-now” moves the team made in the early 2000s. I’ll often hear, “We traded away all those picks for rental players; that’s what bit us!”

But which rental players?

Doug Gilmour (the 2003 edition) and Phil Housley are popular ones, mostly because they were barely even used after the Leafs got them. Ron Francis is another name that comes up a lot and I covered that trade awhile back.

You know who nobody seems to remember the Leafs trading for?

Brian Leetch.

After researching the March 2004 deal, I found some pretty strange stories attached to it all. Let’s take a look at the Brian Leetch trade tree between the Leafs and New York Rangers.

Whoa! OK, at first glance there, it looks like the Leafs gave New York a lot and the Rangers turned that into even more. Eh, not quite.

The Leafs used 14 defenders during the 2003–04 season. Out of those 14 guys, four of them reached 70 games with the Leafs that season: Aki Berg played the most with 79, Bryan McCabe and Bryan Marchment played 75 games each, and Tomas Kaberle played 71. Health and depth on the back end were a bit of an issue so the Leafs looked to add. Leafs GM John Ferguson Jr. signed 37-year-old defender Calle Johansen, for example.

That wasn’t the big splash, though. With the New York Rangers in fire-sale mode, the Leafs sent a first-round pick, a second-round pick and two prospects to New York in exchange for veteran all-star defender Brian Leetch and a pick.

In 54 games with the Rangers that season, Leetch had 36 points and 13 of them were goals. In 15 games to close out the season with the Leafs, Leetch put up two goals and 13 assists for 15 points — a point per game.

Leetch went on to add eight assists in a 13-game playoff stint in Toronto that featured yet another series victory over the Ottawa Senators. Unfortunately for Leetch and the Leafs, the Philadelphia Flyers defeated them in the Eastern Conference semi-final.

The Leafs were still hoping get plenty of use out of Leetch, though. You see, he wasn’t just a “rental” player as he still had a year remaining on his contract. That’s right, the Leafs had Leetch under contract for the 2004–05 season.

There was just one problem: The 2004–05 season never happened.

Toronto paid a small fortune for Leetch in hopes of two deep playoff runs and close to 100 regular-season games if he stayed healthy. Instead, they got just 15 regular-season and 13 playoff games out of him. Then to rub salt in the Leafs’ wound a bit, Leetch signed with the divisional-rival Boston Bruins for the 2005–06 season.

To make matters even worse, the Leafs didn’t get anything out of Roman Kukumberg, the 2004 fourth-rounder the Rangers gave the Leafs. After scoring just eight points in 54 AHL games with the Paul Maurice-coached Toronto Marlies, Kukumberg returned to Europe to play in the Slovak league and KHL. He’s actually still playing pro hockey in the Czech Republic this season.

Great. But what about the other side of the trade? Well, here comes the part where I tell you the picks and players the Leafs gave the Rangers turned into Henrik Lundqvist, Ryan McDonagh, Wayne Gretzky and Batman.

Believe it or not, that didn’t happen.

Jarkko Immonen, a 2002 eighth-round pick of the Leafs, showed some promise in the Rangers’ AHL system and even in 20 NHL games, but ultimately decided to return to Europe. Immonen played in Finland and the KHL, and is still playing in Switzerland this season.

Maxim Kondratiev, a 2001 sixth-round pick of the Leafs, only ever played 40 NHL games: Seven in Toronto, 29 with the Rangers and four with the Anaheim Ducks. The Rangers did manage to flip Kondratiev to Anaheim for a fourth-rounder and Petr Skykora, though. Even still, Sykora had 31 points in 40 games for the Rangers before bolting to Edmonton. The draft pick was later traded and that move didn’t bear any NHL fruit at all.

Alright, the Rangers didn’t get much out of the prospects they got from Toronto but surely the first- and second-round picks panned out, right?

No.

With the 2005 second-round pick the Leafs gave the Rangers, New York selected defender Mike Sauer. As a rookie, Sauer looked promising with three goals and 12 assists in 76 games.

However, early in Sauer’s sophomore season, this happened:

On Dec. 5, 2011, Leafs captain Dion Phaneuf absolutely demolished Sauer with a hit in Madison Square Garden that sent his helmet flying off. This was the last professional hockey game Sauer ever played.

As for the 2004 first-rounder the Leafs gave New York, the Rangers flipped it in a deal with the Flames. Calgary gave New York the 19th-overall pick and an eighth-rounder, back when eighth-rounders were still a thing. In exchange, the Rangers gave Calgary the 24th-overall selection, the pick they got from the Leafs, as well as the compensatory second-round draft pick the Rangers originally received because they couldn’t sign former Vancouver Canucks first-rounder R.J. Umberger.

With the 19th-overall pick, the Rangers selected Lauri Korpikoski. He scored in his first-ever NHL game, a playoff game against the Pittsburgh Penguins. In his rookie season, however, Korpikoski put up just 14 points in 68 games with the Rangers before getting traded to the Arizona Coyotes for Enver Lisin. That didn’t really work out either as Lisin put up just 14 points in 57 games before bolting to the KHL where he plays to this day.

Unrelated to the Leafs but the second-rounder New York gave Calgary ended up being Adam Pinault, who played in only three NHL games. The first-rounder New York gave Calgary, which originally belonged to Toronto, was used to draft Kris Chucko, who played in just two NHL games before having to retire early due to concussion issues.

There is one more player we’re forgetting: The eighth-round pick the Rangers got from Calgary.

With the 247th pick in the 2004 NHL Entry Draft, the Rangers selected Jonathan Paiement. Now, Paiement never made the NHL but he was part of the biggest story in hockey one day while in the Carolina Hurricanes farm system. On Feb. 19, 2009, Paiement was one of the players injured in the infamous Albany River Rats bus crash. In fact, Paiement is cited as one of the players who was injured the most seriously. If you’re unaware of this incident, I highly recommend you read this 2014 post from the AHL’s Charlotte Checkers, who took over as the new Hurricanes affiliate after Albany.

Paiement was done in the AHL after that season but he continued playing in Germany and then later the LNAH in Quebec for several seasons.

Usually when I write these trade trees, I try to figure out the “how” or “why” of a deal and I usually try to say who I think won the trade. What makes this trade so noteworthy is that there are so many players and moving parts involved, and for a variety of reasons, nothing seemed to work out for anybody.

Leetch was supposed to play a full season for Toronto: Lockout. Sauer was in his sophomore season with the Rangers: Career-ending injury. Kris Chucko, the first-rounder the Leafs originally gave New York before it ended up in Calgary: Career-ending injury.

Who in this trade tree worked out the most for the Rangers? If it’s not Sauer, who played in 98 NHL games, then it has to be Sykora, who was with the Rangers for just 40 games.

This isn’t to say the Leafs “gave up nothing” for Brian Leetch.

What did the Leafs need to draft back in 2004? If Toronto’s actual draft is any indication, and with an aging Ed Belfour in net, the Leafs needed goaltending.

In 2004, the Leafs used their first pick, a third-rounder at 90th overall, to draft goaltender Justin Pogge.

At the following draft in 2005, the Leafs got the 21st pick. With that pick, the Leafs selected Tuukka Rask.

Let’s say Toronto keeps their first-rounder, which was 24th overall in 2004. You know who I suspect the Leafs might have drafted? Just two picks later at 26th overall in 2004, the Vancouver Canucks selected Cory Schneider.

If the Leafs had drafted Schneider in 2004, would they have taken Rask in 2005? Maybe doing so could have prevented the infamous Rask-for-Raycroft deal. That’s purely speculation though.

When the Rask-for-Raycroft deal was made, Schneider still had one season remaining at Boston College. Clearly the Leafs wanted a goalie who could play right away. Maybe in some alternate reality, the trade was Schneider-for-Raycroft and then that’s what Leafs fans would be complaining about today.

Let’s say the Leafs had drafted Schneider in 2004 and decided not to draft Rask in 2005. T.J. Oshie went three picks after Rask, Andrew Cogliano was the pick after that, and Matt Niskanen went two picks later. Even names like James Neal and Marc-Edouard Vlasic were picked shortly after.

On both sides, the 2004 Brian Leetch trade between the Leafs and Rangers is a bizarre deal full of questions of what might have been.