Strangest Trades in Sports History

Key Insights

• Baseball has produced the strangest individual trade terms in sports history, including players exchanged for livestock, building materials, and restaurant meals.
• The Herschel Walker trade is the strangest consequential trade in sports history, because the team that gave up Walker got the draft capital that built three Super Bowl championships.
• Several of the strangest trades involved players who turned out to be significantly more valuable than the terms of the deal suggested, which is what makes them strange in retrospect rather than just at the time.

The Baseball Trades That Belong in a Different Category

Baseball has been running long enough, and has operated in enough different economic environments, that its trade history includes transactions that would be impossible to explain to anyone unfamiliar with the sport's early decades.

Lefty Grove Traded for a Fence (1920)

Future Hall of Famer Lefty Grove was sold by Martinsburg to the Jack Dunn's Baltimore Orioles for $3,500, the exact cost of replacing an outfield fence at Martinsburg's ballpark that had been destroyed in a storm.

The fence needed replacing. Martinsburg had an asset they could sell. The transaction produced one of the most direct price discoveries in sports history: a Hall of Fame pitcher was worth exactly one outfield fence in 1920 dollars. Grove went on to win 300 major league games and was considered the best left-handed pitcher of his era. The fence presumably also performed its function adequately.

Johnny Jones Traded for a Turkey

A minor league player named Johnny Jones was traded between teams for a live turkey, which his new organization reportedly raffled off to fans as a promotional item.

The specific details of the transaction, including whether Jones was aware that a turkey was the consideration involved in his transfer, are not fully documented. The turkey's performance during its remaining time with the new organization is also unrecorded. Jones continued his playing career. The turkey's career ended differently.

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Dave Winfield Traded for a Dinner (1994)

The 1994 baseball strike created unusual conditions for several transactions, and Dave Winfield's trade fell into this category. The original terms involved a team dinner as part of the consideration, which the strike disrupted. The sides eventually settled the deal with $50,000 and the promise of dinner at a later date.

Winfield was a future Hall of Famer who had spent most of his career in a high-profile relationship with the Yankees. The dinner-based trade terms arrived late in his career and were more a function of the strike's economic disruption than a genuine assessment of his value, but the documentation of a Hall of Famer being included in a transaction where food was part of the consideration is unusual enough to be permanent.

Tris Speaker Loaned for a Field (Early 1900s)

Boston effectively transferred future Hall of Famer Tris Speaker to Little Rock as payment for the use of their spring training field, with a clause that allowed Boston to purchase him back for $500 if he developed into a major league player.

He developed into a major league player. Boston exercised the option. Speaker went on to win two World Series titles with the Red Sox and was considered one of the greatest center fielders in baseball history. The field rental agreement that briefly included him as a transferable asset is the strangest context in which a cornerstone of multiple championships has ever been involved.

The Consequential Strange Trades

A different category of strange trade is strange not because of the terms but because of what the consequences turned out to be, where the transaction looked questionable at the time and revealed its significance gradually.

The Herschel Walker Trade (1989)

Dallas traded running back Herschel Walker to the Minnesota Vikings for a package of players and draft picks that, through subsequent trades and selections, became the core of the Cowboys teams that won three Super Bowls in four years.

The trade is strange because Minnesota gave up generational draft capital for a running back, and Dallas received that capital and used it to build a dynasty. The Vikings believed they were acquiring a franchise centerpiece. They were correct that Walker was valuable. They significantly underestimated what the draft capital attached to him was worth.

The specific picks and players involved produced Emmitt Smith, Darren Woodson, and Russell Maryland among others, which is a roster core that Minnesota did not have and Dallas did after the transaction. It is the most foundation-building trade in NFL history and simultaneously the worst trade in NFL history, depending entirely on which side of it you were on.

Wilt Chamberlain Traded Mid-Prime (1965)

The San Francisco Warriors traded Wilt Chamberlain to the Philadelphia 76ers in 1965 while he was averaging numbers that no player in NBA history has approached, including a 41.5 points per game season and a 25.1 rebounds per game average.

The return was three players and cash, which was a transaction that required explanation at the time and has required explanation every time it has been revisited since. The Warriors apparently had financial and practical reasons for the deal that made sense in the context of the organization's situation, but the gap between what they gave up and what they received is wide enough that the trade appears on every list of its kind without further qualification needed.

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What Strange Trades Tell Us About Sports

The trades on this list reflect something consistent about how sports organizations make decisions: the value of players is often clearest in retrospect, and the circumstances that produce unusual trade terms often reflect the economic conditions of the organization making the deal rather than a genuine assessment of the player's worth.

Lefty Grove was worth a fence to Martinsburg because Martinsburg needed a fence and had Grove available. The fence was not a reflection of Grove's talent. It was a reflection of Martinsburg's immediate needs and limited alternatives. That pattern, of trades reflecting organizational circumstances rather than player value, produces the strangest outcomes when the player involved turns out to be significantly more talented than the terms implied.

The Herschel Walker trade is the reverse: both sides knew Walker's value. Minnesota just didn't know what the draft capital attached to him would produce, which is a different kind of misjudgment from thinking a Hall of Famer is worth a fence.

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FAQ

What is the strangest trade in sports history?

Lefty Grove for a fence is the strongest answer for individual transaction terms. The Herschel Walker trade is the strongest answer for a trade that was strange at the time and revealed its full strangeness gradually as the picks were used.

Has any team ever traded a player for food multiple times?

The documented record shows it happening in baseball at least twice with different players, which suggests that the sport's minor league system in particular produced enough economic flexibility for food-based transactions to appear more than once.

Why did the Warriors trade Wilt Chamberlain?

Financial pressures and the specific economics of the franchise at that point in NBA history made the deal make sense from San Francisco's organizational perspective even if the player value exchange was clearly unequal. The league was smaller, less commercially developed, and operating under economic conditions that produced decisions which look inexplicable in a modern context.

Did Minnesota ever recover from the Walker trade?

Not within a timeframe that felt proportionate to what they gave up. The Vikings were competitive throughout the 1990s but did not win the Super Bowl during the period when the draft capital they traded was producing championships in Dallas.

Could a trade this strange happen in modern professional sports?

The player-for-livestock trades are impossible in the current economic environment of professional sports. The structurally strange trades, where organizations give up significantly more than they receive because of organizational pressures or misjudged value, continue to happen regularly and are only recognized as strange once the full consequences have developed.

The strangest trades in sports history are the ones where the transaction terms tell you something about the circumstances of the people making the deal rather than the value of what was being exchanged. A fence, a turkey, and a dinner were not assessments of talent. They were solutions to immediate problems that happened to involve human beings as assets. The sport has changed since then. The instinct that produced those trades has not.

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