Worst Sports Trades of All Time

Trades within sports are as old as the games themselves. It used to be the primary form of player movement within leagues — free agency did not exist before the 1970s for MLB and the NHL, and unrestricted free agency began even later for the NBA (1988) and NFL (1993).

Some trades have kick-started dynasties by stockpiling draft picks or landing prized prospects. Other trades have ended great teams before they started. This has happened for a variety of reasons, including a lack of patience for young or developing players, teams overestimating what they’re receiving in return, and even financial issues requiring a hefty contract to be moved.

Let’s look back at the worst of the worst one-sided trades. Some of the moves were recent, so the full ramifications have not been felt yet. Others were bizarre and didn’t even involve the trading of players, draft picks or money. But all of these trades were lopsided and had teams wishing for a mulligan.

The Tampa Bay Buccaneers have the worst win percentage of any sports team from the big four leagues (NFL, MLB, NBA, NHL). What they did in 1987 is a big reason why.

First, they forfeited their rights to Bo Jackson, and the Raiders drafted him. Then, the Bucs traded their 1984 first-round pick, Steve Young, because they felt he was a bust.

Young had a 3-16 record in Tampa, but those results were due more to a lack of talent around him, both on the field and in the front office.

Bill Walsh and the 49ers saw something special in Young, and he became Joe Montana’s eventual successor during the 49ers’ dynasty.

In exchange for Young, the Bucs received two draft picks. Those picks became Winston Moss and Bruce Hill. They were solid players, but Tampa needed stars, and the Bucs let two get away from them in a matter of weeks.

Former Chicago Bulls general manager Jerry Krause has received a lot of flak for his infamous quote: “Players and coaches don’t win championships. Organizations do.”

Of course, the Bulls had the best player in the world, Michael Jordan. But Krause still deserves credit for getting a cornerstone of that dynasty, Scottie Pippen, in one of the most lopsided trades in history.

Krause moved up in the 1987 draft by sending the Seattle Supersonics a couple of draft picks highlighted by Olden Polynice. A 15-year journeyman, Polynice is best known for being arrested for impersonating a police officer. Pippen became an all-time great in Chicago on the way to winning six NBA championships.

Years after the trade, Krause admitted that he knew he was fleecing Seattle’s GM, Bob Whitsitt. “I gave him everything I had, all the garbage I had,” Krause said. “I didn’t have any more to give him.”

The then-Florida Marlins had another one of their offseason fire sales in 2007 as they traded away their best two players in Miguel Cabrera and Dontrelle Willis. They got a haul of six players in return, but only two of them ever did anything notable in the majors, and that wasn’t even in a Marlins uniform.

Cabrera became arguably the game’s best hitter in his new location of Detroit as he won four batting titles, two MVP awards and one Triple Crown.

It seems unfathomable that the Marlins would get rid of a 24-year-old four-time All-Star, but they are a franchise strapped for cash and felt that younger, cheaper players fit their long-term profile more so than an established star.

The Marlins made the same type of trade a decade later by sending away Giancarlo Stanton to the Yankees.

Late Raiders owner Al Davis always loved sticking it to the rival Denver Broncos, and in 1967, he straight-out hustled coach/general manager Lou Saban.

The Broncos were a losing franchise with cornerback Willie Brown, so they figured they couldn’t be much worse without him and sent him to Oakland for a third-round draft pick.

Brown already was a two-time Pro Bowler in Denver, but he became a Hall of Famer in Oakland, making another seven Pro Bowls and four All-Pro teams.

Brown played in 17 postseason games in a Raiders uniform while the Broncos had just four playoff games over the same span.

As for the person Denver drafted with that third-round pick, Mike Current, he turned into a starting offensive tackle but not an impact player like Brown.