The 25 Strangest Trades in Sports History

Trade season has become a 12-month event in professional sports, as teams constantly look for ways to make themselves better. Even when one league’s trade deadline passes, another pops up in its place to fill the void and supply ravenous fans with the kind of intrigue and rampant speculation that helps feed the 24-hour sports news cycle. In the end, though, most trades end up being pretty boring: players are swapped for other players, or sometimes cash or draft picks. This lack of variety can be, dare we say, boring.

However, some general managers dare to be different. We don’t always give them the credit they deserve, but some are capable of being very creative. While this rarely happens in the major professional leagues nowadays, there are still instances where a coach like Doc Rivers will make headlines as part of an odd compensation exchange.

The smaller, more fringe leagues are where strange things tend to happen, and immortalize guys like Ken Krahenbuhl and Walter Restrepo who become the centerpieces of absurd deals. Whether it’s in exchange for food, equipment, or something else entirely, here are the 25 Strangest Trades in Sports History

25. Ozzie Guillen for Two Players to be Named Later

Year: 2011

This may not come as a surprise to you, but managers neither throw the ball nor swing the bat. Their ability to win or lose games for their club is minimal when compared with the impact an actual player has. However, in a fit to get some publicity, teams sometimes lose sight of that, which leads to things like the Marlins "acquiring" manager Ozzie Guillen from the White Sox in exchange for two players to be named later.

As usually happens in these types of deals, it didn't really work out for anybody; Guillen is no longer with the Marlins, and prospects Jhan Mariñez and Osvaldo Martínez are no longer with the White Sox organization.

24. Stan Van Gundy for Draft Picks

Year: 2007

It's funny to think of a time when Stan Van Gundy was an NBA coach in high demand, but that was indeed the case during the 2007 offseason. The "master of panic" had been forced out by Pat Riley (or resigned of his own volition, depending on who you believe) in 2005-06, but still had his contract controlled by Miami. He actually turned down an offer from the Pacers first, but then became the default choice of the Magic when Billy Donovan backed out of his original deal with Orlando.

The Heat in return received the Magic's second round draft pick that year, and either the right to swap first rounders or another second round pick and cash the following year.

23. Jon Gruden for Draft Picks and $8 million

Year: 2002

There was something about the infamous "Tuck Rule" game that ruined Oakland for Jon Gruden, and after the 2002 playoff debacle he was ready to move on. Apparently so was Al Davis, who was not enamored of Gruden's low-risk passing philosophy and was thus all too happy to let "Chucky" go when it came time to discuss whether the situation could be salvaged. The Buccaneers swooped in with a monster offer, giving up their first round picks in 2002 and 2003 as well as second rounders in 2002 and 2004. Since Tampa won the Super Bowl that year, we'll go ahead and guess it was worth the sacrifice.

22. Chuck Tanner for Manny Sanguillen

Year: 1977

Chuck Tanner's first year as manager of the Oakland A's was marginally successful, but the team ended up finishing 2.5 games out of first and missing the playoffs. Loaded with expensive veterans who were past the prime, Oakland was ready to turn the page and start over; apparently, that also meant moving on also from their manager. The A's dumped Tanner to Pittsburgh in exchange for aging catcher Manny Sanguillen, who actually was a pretty solid player in his younger days and owns the tenth-highest batting average for catchers in MLB history.

Things worked out just fine for Tanner, who led the 1979 "We Are Family" Pirates to a World Series championship.

21. Lou Piniella for Randy Winn

Year: 2002

How much is a manager really worth? If you ask the Tampa Bay Devil Rays, they'd say more than an All-Star outfielder. That is the only justification we can find behind their decision to acquire manager Lou Piniella from the Seattle Mariners while sending them Randy Winn, who was basically Tampa's only decent player. Predictably, this trade did not work out especially well for the Rays; Piniella lasted just three years, going 200-285 and accepting a $2.2 million buyout to bring an end to his borderline-disastrous tenure.

20. Kerry Ligtenberg for $720 Worth of Baseball Equipment

Year: 1996

While Kerry Ligtenberg was not drafted out of college in 1994, he found his way into a Major League organization thanks to his team's need for some additional equipment. Pitching in the independent Prairie League and with just one class credit to go until he got his degree in engineering, Ligtenberg looked like he was on his way out of baseball in early 1996. However, his manager convinced the Braves organization to take a chance on the young reliever who had very briefly appeared as an MLB replacement player in 1995.

Since he was going to use the extra cash for equipment anyway, the manager cut out the middle man and asked for a purchase price of twelve dozen baseballs and two dozen bats. Not surprisingly, the Braves had no problem affording that.

19. Doc Rivers for a First Round Draft Pick

Year: 2013

The Celtics actually got pretty lucky with this one, considering that coach Doc Rivers was definitely going to leave no matter what as soon as they traded Kevin Garnett and Paul Pierce to Brooklyn. We can't say we blame him, either; would you want to have a front row seat for three years of The Gerald Wallace Show? The Clippers' willingness to fork over their 2015 first round pick in exchange for Doc's services made this an easy deal, and one that has worked out well for both teams to this point.

18. Bill Belichick for Draft Picks

Year: 2000

We're pretty sure the Patriots would do this one again. When Bill Parcells stepped down as head coach of the Jets, he had already appointed defensive coordinator Bill Belichick as his successor. The only problem was that, apparently, Belichick wasn't into it. Rather than introduce their new coach at the pre-scheduled press conference, the Jets were shocked as Belichick scribbled a typically-terse resignation letter (the entirety of which read "I resign as HC of the NYJ") and about a month later was hired as head coach of the Patriots.

Because he was still technically under contract with the Jets, though, the Patriots were forced to "trade" their 2000 first round pick in exchange for the coach's rights.

17. Lefty Grove for a Fence

Year: 1920

Ah, the good ole days when a baseball team could be so cash-poor that they didn't even have a fence around their field. Such was the case for the Martinsburg Mountaineers of the Blue Ridge League, who lacked financial resources but had one major asset: Lefty Grove. When the minor league (at the time) Baltimore Orioles came clamoring for Grove's services, Martinsburg saw an opportunity and took it. They sold their ace for $3,500, enough for them to finally get that dream fence around their field. The players probably appreciated it, considering to that point they had been forced to play the entire regular season on the road because of the condition of their home field.

16. Tim Fortugno for a Bag of Balls and $2500

Year: 1989

Tim Fortugno was the definition of a minor league journeyman, a left-handed reliever who managed to pitch in 450 games before finally making it up to the Majors in 1992. With an MLB career that lasted just 76 appearances, it's a wonder we remember him at all. However, Fortugno has two entries in the annals of baseball history that keep his legacy alive: he surrendered George Brett's 3,000th career hit, and in 1989 his Reno Silver Sox team sent him to the Brewers organization in exchange for a little cash and a fresh bag of baseballs.

15. Harry Chiti for Harry Chiti

Year: 1962

Harry Chiti, who was primarily a backup catcher, was also a pioneer when he became the first man to functionally be traded for himself. His Cleveland Indians squad traded him to the New York Mets at the beginning of the season for a little cash and a player to be named later. By June, the Mets decided that they no longer wanted poor Chiti (who was hitting .195 at the time), and decided that he should be the aforementioned "player to be named later." Since the deal in essence was a little cash in exchange for his temporary services, he was in fact the first literal "rent-a-player" in modern baseball history.

14. Cy Young for a Suit

Year: 1890

If we were to tell you that you could acquire the winningest pitcher in the history of baseball in exchange for a fine suit and $300, is that something you might be interested in? That's all it took for the Cleveland Spiders to get Cy Young, who was then pitching for Canton, Ohio in the Tri-State league. At the time, he was actually known as "Dent," a shortened version of his real first name Denton. He would come to be known as Cy the next year, when his teammates began to call him "Cyclone" due to the speed and movement of his pitches.

13. Bill Parcells for Draft Picks and a Charitable Donation

Year: 1997

In what would turn out to not be the last coach swap between the organizations, the Patriots and Jets wrangled over compensation after Bill Parcells decided to leave New England after falling in the Super Bowl. The Jets had decided to work around a clause in Parcells' contract that prevented him from coaching anywhere else by hiring his lead assistant Bill Belichick as head coach, then bringing on Parcells as an "advisor." When the Patriots threatened legal action, commissioner Paul Tagliabue brokered a deal that saw the Pats receive the Jets' third and fourth round pick that year, their second round pick the following year, their first round pick the year after that, and a $300,000 donation to the Patriots' charitable foundation.

12. John McDonald for John McDonald

Year: 2005

The "player to be named later" is a staple of MLB trades, and it often signifies that a team just wants to dump a player and does not care who they get in return. Toronto fan favorite John McDonald was a part of one such trade, shipped out of town in July of 2005 to Detroit in exchange for the aforementioned "future considerations." When it came time for the Blue Jays to collect on the Tigers' debt, they were repaid with a familiar face: John McDonald. Despite a decent enough stint as a backup for the Tigers, they decided they'd actually give Toronto a little extra cash for the trouble of taking their old player back.

11. Keith Comstock for a Bag of Balls

Year: 1983

Keith Comstock actually went on to piece together a long career for himself, which considering where he started was a big accomplishment. After starting in professional baseball in 1976, he spent 14 years in the minor leagues before making it up to the Majors and winning seven games out of the Mariners' bullpen in 1990. Along the way, he was given the double indignity of not only being traded for a bag of baseballs (and $100), but having to deliver said baseballs to the minor league facility of his new team.

10. Joe Gordon for Jimmy Dykes

Year: 1960

Fan bases and team management alike can quickly grow weary of their managers when the losses start to pile up, and after a year of frustration the Detroit Tigers and Cleveland Indians began to feel that way about their respective skippers, Jimmy Dykes and Joe Gordon. So what did they do? The teams decided in August to swap managers, with the two beleaguered bosses changing sides in an attempt to spice things up for their teams. The move did not really work out as hoped, as both teams missed the playoffs and failed to improve in any discernible way.

9. Cliff Dapper for Ernie Harwell

Year: 1948

It's rare nowadays for announcers to be so beloved that teams keep them around for more than a couple years. Back in the 1940s, though, broadcasters were apparently all the rage. With their regular play-by-play man ailing, the Brooklyn Dodgers called the Atlanta Crackers to inquire about "calling up" future legend Ernie Harwell. Sensing an opportunity, the Crackers' owner demanded a player in return for letting Harwell out of his contract; the Dodgers ended up surrendering minor league catcher Cliff Dapper, who had accumulated just 19 career MLB plate appearances and who would never earn another one, toiling away at the lower levels of professional baseball until retiring following the 1957 season.

8. Walter Restrepo for Two Nights of Hotel and Transportation Arrangements

Year: 2014

Nobody ever said playing in the second-level professional soccer league in the USA was especially glamorous. When you run one of these threadbare teams, you do what you can to make things work financially, including making any kind of creative deal you can find. Midfielder Walter Restrepo found that out the hard way just after the New Year in 2014, when his Fort Lauderdale Strikers team sent him to the San Antonio Scorpions in exchange for hotel accommodations and transportation to and from the game on their two visits to San Antonio this season.

Restrepo (who had been part of the league's Best XI in 2012) will suit up for San Antonio when the season starts in April.

7. John Odom for a Bag of Baseball Bats

Year: 2008

We won't say too much about John Odom, whose most notable moment of his career was being traded for a bag of bats in June of 2008. The pitcher struggled with a lot of personal demons, which caused him to quickly bounce from the Giants' minor league system to the independent Golden Baseball League, and sadly to overdose and lose his life in November of that same year.

6. Fred Roberts for Two Preseason Games

Year: 1986

6'10" Fred Roberts was not an athletic specimen by any stretch, but he did enjoy a long and reasonably productive professional career as he spent time in both the NBA and Europe. After attending BYU, Roberts came back to Utah to play for the Jazz in what was one of the most natural fits of all-time. The defending champion Boston Celtics, though, needed depth in the frontcourt and made Utah an offer they couldn't refuse: a third round pick, and the right to play the Celtics twice the following preseason. Apparently, the Jazz didn't think much of Roberts after all.

5. Ken Krahenbuhl for 10 lbs. of Catfish

Year: 1998

OK, so there was a bit more to the trade of Ken Krahenbuhl from the Pacific Suns to the Greenville Bluesmen than just 10 pounds of catfish. The Suns did also receive a player to be named later and some cash. But really, what's the fun in that? Perhaps motivated by being exchanged for a heinously ugly fish, Krahenbuhl went out in his first start after the trade and promptly threw a perfect game.

4. Dave Winfield for Dinner

Year: 1994

Dave Winfield is a Hall of Famer, but that doesn't mean he is immune from the weird world of baseball trades. His involvement came at the very end of his career, when the Twins were looking to part with their 40-year-old outfielder during the 1994 players' strike. They struck a deal with the Indians to swap Winfield for a player to be named later, but when the season was canceled, the teams were stuck. To ensure the trade went through, the Twins' executives took their Cleveland counterparts out for dinner and paid the tab, effectively trading Winfield for some steaks masquerading as "cash."

3. Johnny Jones for a Turkey

Year: 1931

Joe Engel (the man in the picture) was a circus promoter masquerading as a baseball man, a guy who is really the godfather of turning minor league baseball games into a spectacle. As director of baseball operations for the Chattanooga Lookouts, Engel was known for putting on all manner of publicity stunts; he had a duck lay an egg on second base, and one game had the team ride into the field on elephants. Perhaps his crowning achievement, though, was when he decided to trade light-hitting shortstop Johnny Jones to the Charlotte Hornets in exchange for a 25-pound turkey.

His justification? "The turkey was having a better year."

2. Tom Martin for a Bus

Year: 1983

Tom Martin did not end up getting a ton of on-ice action in the NHL, but that doesn't mean he wasn't useful. In addition to being a standout on the minor league level, he also helped his Seattle Breakers team secure some fresh wheels when their old team bus broke down. The Victoria Cougars just happened to have two (side note: what minor league hockey team just has an extra bus laying around?), so a deal was quickly struck and Martin would thus forever be known around the league as "Bussey."

1. Babe Ruth for "No No Nanette"

Year: 1919

OK, so technically this trade was just for cash, but that cash was allegedly earmarked for a specific purpose: funding a Broadway musical. Infamous former Red Sox owner Harry Frazee was so enamored of the theater that he was willing to sacrifice star pitcher and emerging power hitter Babe Ruth, who had just set the single-season record for most home runs (29). "No No Nanette" became the impetus for the Yankees acquiring one of the greatest players in the history of baseball, at least according to legend.

The exact nature of Frazee's need for immediate financial relief is not actually known, and it can't be ignored that Ruth was also making the outlandish (at the time) demand for a $20,000 per year salary.