So often we delve deep into the analytical side of trades in sports. Which players needed the change more? Which team is going to come out on top? Was there even a winner or loser in the deal? Did they overpay for a star or underpay for a valuable role player?

All these questions drive the discussions that stem from these sorts of transactions in any professional sports league. On top of that, the analysis can go on for some time. It’s never too late – or for some too early – to look back on a deal and raise these questions.

In hockey, we’ve long discussed trades from over the years. From the day Wayne Gretzky was traded by the Edmonton Oilers to more recent deals like the Alexei Yashin trade from the Senators or the Phil Kessel deal that sent him to Toronto or Pittsburgh, it’s a never-ending look into the trade itself.

But what if I told you that there were two trades in particular that cost teams less than what it costs nowadays for a chocolate bar? Yes, that’s right. Forget about the first $1-million man in hockey, let’s talk about two one dollar players that went on to have successful NHL careers.

A Sheppard Worth the Money

The first happened on July 9, 1990, in a trade between the New York Rangers and the Buffalo Sabres.

After the Sabres drafted him in the third round of the 1984 NHL Entry Draft, the team shipped Ray Sheppard to the Rangers for one dollar.

The thing is, Sheppard wasn’t a horrible player to begin with. In fact, he tallied 65 points in 74 games in his rookie season with Buffalo in 1987-88 and managed 114 points in 159 regular season games prior to the trade. Still, the Sabres moved the, then, 24-year-old to the Rangers for cash and future considerations that later turned out to be one dollar.

Sheppard played just one season with the Rangers – notching 24 goals and 47 points in 59 games before signing in Detroit as a free agent in the summer of 1991.

With stops in Detroit, San Jose, Florida and Carolina to finish his career, Sheppard went on to score 357 goals and 657 points in 817 regular season games – retiring after the 1999-2000 season as a member of the Panthers. He added 50 points in the postseason in 81 career games, but never hoisted the Stanley Cup.

While he may not have been one of the most dominant players during his time in the NHL, it’s safe to say that he was far more valuable than the one dollar he was once traded for. But that wasn’t the last time it happened in the NHL.

Trading Paper for Draper

Nearly three years later, the Detroit Red Wings acquired one of their biggest role players of the 1990s and 2000s in Kris Draper for, you guessed it, a dollar. The Wings paid just one dollar to the Winnipeg Jets for Draper who was drafted in the third round, 62nd overall, by the Jets in 1989.

While he was never the most offensive player, Draper became a major cog in the Red Wings success during his tenure. His best offensive season came in 2003-04 when he tallied career-highs with 24 goals and 40 points.

He only recorded 361 points in 1,137 career regular season games for the Red Wings and 364 over his entire career, but it was what he did without the puck that made him such a valuable piece – one the Red Wings held onto for 17 seasons.

From 2000 to 2009 he was continuously in the Selke conversation – even if he was a long-shot to some of the other candidates. That said, he took home the award in 2003-04 and was even in the Hart conversation finishing 28th in voting.

His success continued into the playoffs with the Red Wings where he had 46 points in 220 games en route to four Stanley Cups with Detroit. That included back-to-back wins in 1997 and 1998 with the other two coming in 2002 and 2008.

He was a major role player in the igniting of the rivalry between the Red Wings and Colorado Avalanche and gave the Wings depth up front with defensive responsibility. While he will never be remembered for what he did on the offensive end, he was worth far more than the lone dollar the Red Wings spent to get him.

Whatever the case, Sheppard and Draper are easily two of the cheapest acquisitions the NHL has seen in recent memory.

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