We all love getting a good deal — almost as much as we hate the feeling that comes when we realize we drastically overpaid for something. And no one is immune from overpaying, even general managers of some of the biggest sports franchises in the world. After all, these teams do not possess unlimited resources, and every contract in the MLB, NFL, NBA or NHL counts against their budget. When general managers discover a future Hall of Famer in the sports equivalent of the bargain bin, they get both an elite player for their team and financial savings. As such, the right trade or signing can set up a franchise for a decade — or if it goes wrong, it can leave an organization saddled with underperforming players earning huge salaries that hamper a team for years.
With that in mind, here’s a look at some of the best and worst deals in sports history.
Best Deals in Sports History
Some trades have turned out to be so lopsided, so utterly fantastic for the team getting the better end of it that they’ve become enshrined in the sports lexicon for all time. That’s because an astonishingly great trade or player signing or two frequently occurs at the start of every great dynasty. When teams can flip a player they really can’t use or don’t need for a crucial piece to the team puzzle, it makes it that much easier to build toward long-term success.
Mike Trout With Every Contract He's Signed
You might be reading this and wondering, “Sure, Mike Trout’s good but how great can a deal be when he’s not just one of the highest-paid MLB players in the world, but the highest paid?” Even so, the 12-year, nearly $430 million deal — among the biggest sports contracts of all time — that Trout signed with the Los Angeles Angels in March 2019 would still appear to be a bargain for the Angels. That is, it will be if he plays half as well as he did on his previous, lower-paid contracts.
When you’ve accumulated more WAR — a fancy baseball stat for tracking a player’s overall value — at age 27 than multiple Hall of Famers did over the course of a career (Tony Gwynn, Ryne Sandberg and Ernie Banks, just to name a few), you have to reset expectations. Data journalism site FiveThirtyEight calculated what Mike Trout’s annual salary should be based on the 2018 season. That figure? A whopping $79 million, or more than double the approximately $35 million a year he’ll average under this new deal.
Miguel Cabrera to the Detroit Tigers
If you just look at the pieces involved, this wasn’t necessarily all that lopsided of a trade. The Detroit Tigers acquired Miguel Cabrera — one of the greatest hitters of his era — and a starting pitcher from the Florida Marlins, giving up six prospects in return. Two of them, outfielder Cameron Maybin and pitcher Andrew Miller, went on to become solid major leaguers, but Cabrera already was a star. Acquired at age 24, he was a four-time All-Star selection by then.
Unfortunately for the Marlins, Miller and Maybin didn’t emerge as front-line players while wearing a Marlins uniform. Miller flamed out as a starter for the Marlins, winning just 10 games in three seasons in Florida before remaking himself as an elite reliever, while Maybin’s value as a speedy outfielder with strong defense wouldn’t really emerge until his time with the San Diego Padres three years later. Regardless, the Tigers gave up very little and got the man who anchored their lineup for a decade — winning two American League Most Valuable Player awards in that span — making this a spectacular deal for them.
Brett Favre to the Green Bay Packers
Brett Favre long has been considered the quintessential Packer, building a bond with the team and its Green Bay fan base that’s rarely been matched across the sporting world. But Brett Favre almost never was a member of the Packers.
Favre was drafted by the Atlanta Falcons in 1991, and that season, he saw action in two games. He attempted four passes in a Falcons uniform and two of them were caught — by the other team. That’s why — despite being on the verge of a stroke of luck on a positively cosmic scale — the Packers shot down the trade for Favre internally. Twice. Many simply saw a young quarterback with personal flaws who, literally, threw an interception on every other pass attempt. But, the Favre skeptics ultimately lost out, and the Packers ended up getting their GOAT for one of their two first-round draft picks in 1992.
In 16 seasons in Green Bay, Favre threw for 61,655 yards and led the Packers to consecutive Super Bowls, in 1997 and ’98, winning the first of the two.
Frank Robinson to the Baltimore Orioles
There might be no two words more devastating to longtime Cincinnati Reds fans than “Milt Pappas.” That’s because Pappas, a pitcher, was the centerpiece of the three-player package the Baltimore Orioles sent to the Reds for future Hall of Fame slugger Frank Robinson in 1965. Pappas ended his career with 209 wins, but only 30 of them came in Cincinnati, where he spent two-plus seasons. On the flipside, in his first season in Baltimore, Robinson won the Triple Crown, the American League MVP award and the World Series MVP trophy as he led the Orioles to the 1966 world championship. In fact, Robinson remains the only player ever to win the MVP in both the American and National League while Milt Pappas remains a name not to mentioned in Cincinnati.
Randy Moss to the New England Patriots
The opinion that wide receiver Randy Moss was washed up was wrong. Languishing with the Oakland Raiders, Moss and his NFL contract were shipped to the New England Patriots before the 2007 season, and he resurrected his career on a team that wasn’t dysfunctional.
Once he joined the Patriots, Moss looked like the touchdown machine who terrified the league in Minnesota early in his career. He grabbed 50 touchdown passes in just 52 games with the Pats. And the cost to New England? Try a single fourth-round draft pick that the Raiders used to take John Bowie — a defensive back whose entire NFL career consisted of coming off the bench in some five games.
John Smoltz to the Atlanta Braves
Most of the trades are only among the “best” if you’re a fan of the right team. However, the trade that sent minor leaguer John Smoltz from the Detroit Tigers to the Atlanta Braves for Doyle Alexander in 1987 is a rare gem in that both sides got what they needed. The Tigers needed another arm as they made a push to the postseason, and Alexander tallied a 9-0 record in 11 starts with a 1.53 ERA down the stretch. Detroit fell short of the pennant, losing to the Minnesota Twins in the ALCS.
Granted, the Tigers fell short of the World Series and Smoltz, a Detroit native, spent 20 of his 21 seasons in Atlanta, winning the 1996 Cy Young Award and later being enshrined in the National Baseball Hall of Fame. It’s still worth noting that both sides of this deal got exactly what they needed. Alexander was dominant with Detroit in 1987, and Smoltz was a key piece of Atlanta’s incredible run of success in the 1990s.
All of the Vikings Draft Picks for Herschel Walker
In the history of lopsided trades, there might not be one quite as incredible as the deal that sent running back Herschel Walker from the Dallas Cowboys to the Minnesota Vikings.
And there are multiple aspects to the trade. One is how Walker failed to pan out as the elite running back Minnesota expected him to be. The other is that the Dallas Cowboys got a truly incredible return: five players and six draft picks. And, perhaps most tellingly, it was those very draft picks that ended up turning into a huge chunk of the core that would go on to produce the Dallas dynasty of the early to mid-1990s. So, basically, the Cowboys ended up trading Herschel Walker for… three Super Bowl titles. Which is a GREAT deal.
Lou Brock to the St. Louis Cardinals
It’s satisfying for fans when their team acquires a player who turns out to be everything they hoped — and more — and the player they traded turns out to be a disappointment. It’s even better when a team makes this trade with an opponent in the same division.
That’s what happened in 1964 when a pair of archrivals, the St. Louis Cardinals and Chicago Cubs, each traded three players for three players in return. The principals involved in the trade were pitcher Ernie Broglio and outfielder Lou Brock, and Brock to the Cardinals is the prime example of the baseball adage: Never trade within your division.
Broglio, who later admitted he had an arm injury with the Cubs, lost his stuff, pitching two-plus seasons in Chicago and winning only seven games. He was out of baseball after the 1966 season while Brock played for the Cardinals through 1979. Brock had a lifetime batting average of .293 and stole 938 bases.
For the Cardinals, it was one thing to acquire a future Hall of Fame member, but it was even better for their rival to be reminded of their bad deal in about 20 meetings a year for 15 seasons.
Babe Ruth and the Curse of the Bambino
You’ve probably already heard the tale of the Curse of the Bambino, but here’s a quick review, just in case. After winning the 1918 World Series behind the incredible pitching (yes, pitching) of young star George Herman “Babe” Ruth, Boston Red Sox owner Harry Frazee sold him to the New York Yankees as the owner coped with financial problems. The deal, executed on Dec. 26, 1919, called for a payment of $25,000 upfront and three subsequent annual payments of $25,000. It’s been said that Frazee, a New York theater owner, sold Ruth and other players because he needed the cash after his plays lost money.
With the Yankees, the Babe — whose titanic legacy basically defined the sport for the next century — gave up pitching and played in the outfield. He was with the Yankees from 1920 to 1934 and by the time he retired, he had hit 714 home runs, a major league record that stood until 1974.
The Red Sox wouldn’t win the World Series again until 2004 when the Curse of the Bambino is believed to have been broken, while the Yankees racked up 26 World Titles over the same period.
Cheap Food at Atlanta's Mercedes-Benz Stadium
OK, so this one is here for the fans — and their wallets. For years, fans at pro stadiums and arenas have paid exorbitant prices on beer, hot dogs and all other concession items. It’s outrageous, but it’s been the standard for as long as anyone can remember.
Thank goodness, then, for Mercedes-Benz Stadium in Atlanta, where prices before the 2017 NFL season were cut in half for fans attending Atlanta Falcons games. A hot dog for $2? Perish the thought! But, get this, once vendors stopped pricing food in a way that was transparent extortion, customers were more ready to buy. Per-fan spending increased by 16% despite everything costing half as much. And now, fans of the Falcons and their stadium co-tenant, Atlanta United of MLS, are benefiting from an 11% decrease on the already reduced prices of a handful of popular items. Hot dogs now are $1.50, with chips and salsa costing $2.50. In 2019. Cue the apocalypse.
Worst Deals in Sports History
When you’re a GM trying to build a team that’s going to be good, and also better than every other team in the league, you have to take some chances. And once free agency became the norm across professional sports, that meant that sometimes that fight to be the best actually ended up pushing teams in the opposite direction. Whether it’s mortgaging the franchise’s future by trading away the best young players or turning a past-prime star into the undeserving highest-paid athlete in the league, a really bad deal can cripple a franchise for years.
Jerome James Signed By the New York Knicks
Every once in a while you see a professional athlete act in a way that is pretty familiar: A big-time star signs an enormous contract, only to seemingly lose all drive and ambition once the ink dries. If you were set for life financially, you might think, “Yeah, I bet I’d do the same thing.”
As such, let’s all take it easy on Jerome James. Sure, New York Knicks fans probably expected a whole lot more when the center signed a five-year, $30 million deal with the team prior to the 2006 season. Still, James was out of shape throughout his Knicks tenure, even getting suspended during his first season with the team for being unprepared to practice. But ask yourself this: If you were living in New York City with $30 million, how much attention would you pay to your job?
James played 90 games over four seasons for the Knicks, averaging 2 1/2 points per game.
Mike Hampton, Denny Neagle (and Basically Any Other Pitcher) Signed By the Colorado Rockies
The thin air in the Mile High City has made playing baseball in Denver a very interesting proposition. With less air resistance, baseballs fly farther, turning more routine flies into home runs when you’re playing at Coors Field. That’s been great for Colorado Rockies hitters, but it’s also meant the franchise has had a devil of a time establishing pitchers who keep their spirits up while pitch after pitch has the potential of getting clocked into the stratosphere.
The Rockies have signed some big free-agent pitchers, hoping to buck the trend. And those same huge deals have typically flamed out in the worst way. The two that really stand out? The deals signed by Denny Neagle and Mike Hampton, on whom the Rockies spent $172 million prior to the 2001 season with disastrous results.
In a combined five seasons with the Rockies, they won 40 games. Both saw their ERA swell to over 5.50 during those years.
Albert Pujols Signed By the Los Angeles Angels
Is Albert Pujols the best right-handed hitter of all time? Based on his time with the St. Louis Cardinals, the argument could be made that he is. But limit your observations to his time with the Los Angeles Angels and it would be hard to draw the conclusions that he’s much more than a marginal power hitter. That’s because Pujols did what all humans do: age. And for the Angels, who signed Pujols to a massive 10-year, $254 million deal in late 2011, a few weeks before his 32nd birthday, that means the team probably could (and should) have seen this coming.
Pujols hit .245 in 2018 — about 60 points below his career average of .301 — and got paid $27 million to do it. And whether Pujols ever plays another game for the Angels beyond the 2019 season, he’ll pull down $29 million in 2020. And $30 million the season after that.
Miguel Cabrera Re-signed By the Detroit Tigers
Miguel Cabrera has the interesting position of appearing on this list twice, once because the Marlins overestimated the value of a bunch of Tigers prospects, and now because the Tigers probably overestimated just how much longevity Cabrera would have. Not unlike Albert Pujols, Cabrera is a once-incredible, future Hall of Famer who signed an eight-year, $248 million contract extension in his early 30s that is already looking disastrous. The contract runs through at least 2023 when he’ll be 40.
What makes the Cabrera deal worse than the Pujols contract? The Tigers had the Pujols deal as an example of what not to do. Cabrera already has begun to struggle to stay healthy, and it appears as though the Triple Crown-winning version of Miggy has slipped away.
Gilbert Arenas Re-signed By the Washington Wizards
The story of how the re-signing of local favorite Gilbert Arenas by the Washington Wizards went wrong is truly epic. After all, Arenas was among the league’s best players when he signed the six-year, $111 million pact in 2008. However, Arenas later brandished a gun in the locker room, threatening a teammate over a gambling debt. And, well, that was that.
In Arenas’ defense, the gun was not loaded — rather ironic given that their team was called the Bullets until 1997 — but it still resulted in a suspension. Between that incident and a rash of injuries, Arenas was never quite the same. But regardless, you pay someone $111 million, you really expect them not to pull a gun on a co-worker.
Bobby Bonilla Deferred By the New York Mets
The New York Mets signed free agent outfielder Bobby Bonilla to a five-year, $29 million deal in 1991 that, at the time, made him the highest-paid player in MLB history. The team traded him away, and when he became a free agent again in 1996, he signed a new deal with the Florida Marlins. Fast forward, and Bonilla wound up back with the Mets in 1998. After the 1999 season, the Mets decided to part ways with Bonilla, still owing him the $5.9 million remaining on the contract he signed with the Marlins.
The Mets’ owners — the Wilpon family — wanted to sign other free agents and Bonilla agreed to defer his pay over 25 years at 8% interest. By doing so, Bonilla would receive $1.19 million each July 1 from 2011-35, turning his $5.9 million owed into $29.8 million. A side note: Always take the lump sum if you win the lottery… unless they’re offering you 8% interest to defer.
Why were the Wilpons willing to offer a deal like this? Because they had a magical money manager who routinely produced 12% to 15% annual returns — almost double the interest rate the Mets would pay Bonilla. Not only would that mean deferring Bonilla’s contract would pay for itself, they expected to turn a profit on the deal. The name of that money manager? Bernie Madoff. Oops.
Josh Hamilton Signed By the Los Angeles Angels
Josh Hamilton’s story is a heartwarming tale of redemption that should help everyone have more hope for the future. Unless you’re a Los Angeles Angels fan, that is. The Disney version of Hamilton’s story ended, ironically, right before he arrived in Anaheim.
Hamilton was the No. 1 pick in the 1999 MLB draft but addictions to drugs and alcohol sent his life spiraling out of control, and his once-promising baseball career was shattered. But Hamilton got himself sober and bounced back, ultimately winning the 2010 AL MVP with the Texas Rangers. That helped him land a five-year, $125 million deal with the Angels prior to the 2013 season. Only Hamilton’s story had another reversal, and the Angels gave up on him after just two seasons. He hit .255 with 31 homers in his brief career with the Angels.
Eric Lindros to the Philadelphia Flyers
It’s hard to remember, but Eric Lindros used to be considered a savior in skates. He put up the sort of numbers across his juniors career that had the NHL positively drooling over what his incredible combination of size, agility and hands would mean. As such, the Philadelphia Flyers decided to empty out their farm system to get the guy they envisioned anchoring their franchise for years to come — sending two first-round draft picks, six players and $15 million to the Quebec Nordiques for the young star.
However, Lindros never reached his ceiling, ultimately falling victim to persistent injury problems. And the haul of prospects sent to the Quebec Nordiques? It included Hall of Famer Peter Forsberg and helped set the franchise up to win two Stanley Cup titles after it moved to Colorado to become the Avalanche.
Charlie Weis Re-signed By Notre Dame
So Charlie Weis’ tenure as Notre Dame’s football coach wasn’t necessarily that bad based on his 35-27 record alone. But when you factor in the sort of enormous institutional advantages for big-name schools in college football, 35-27 with Notre Dame is actually pretty bad. Know why that’s so clear? Because when Notre Dame decided to fire Weis, it came at a price so steep it should be clear administrators felt they had no other choice.
Bill Belichick-protege Weis finished 9-3 in his first season at Notre Dame (2005), coming within a foot of knocking off top-ranked USC. That prompted the university to panic that others would pursue him and offer Weis a stunning 10-year extension worth an estimated $40 million. By the time it was clear Weis actually was terrible at coaching college football, it was too late and the school had to buy out his contract. When the deal finally reached its end in 2015, Notre Dame had paid Charlie Weis an estimated $19 million NOT to coach for them.
Matt Millen Re-signed By the Detroit Lions
Few names will send a Michigander spiraling into rage faster than that of Matt Millen. While the rest of the country might see Millen as a wonderful color commentator whose fine career was only somewhat marred by his failed stint as an NFL general manager, Detroit Lions fans have to remember how the season they went 2-14 wasn’t the low point.
While Millen’s initial contract was one thing, his extension prior to the 2005 season was about as indefensible as it gets. Millen’s Lions had amassed a pitiful 16-48 record across his first four seasons leading the team — a team that was a last-second field goal away from the playoffs the season before he took over in 2001. However, Aug. 4, 2005, must have been Opposite Day in Detroit, because instead of firing Millen, the Lions decided to give him another half-decade to work out the kinks. Millen only lasted another two seasons and change. He was fired after Week 3 of a 2008 season in which the Lions became the first franchise ever to finish 0-16.
Wayne Gretzky to the Los Angeles Kings
Why is this among the worst trades? Because everyone lost. Wayne Gretzky, a player of such unparalleled excellence that his nickname is simply “The Great One,” began his career winning four Stanley Cups in five years for the Edmonton Oilers — Canada’s favorite son redefining the national sport. And after a 1998 trade to the Los Angeles Kings, Gretzky played 12 more seasons but never reached the pinnacle of success again.
Gretzky had only one more chance to win a Stanley Cup in the final 10 years of his career, but he didn’t get the chance to do so in front of the hockey-mad Albertans. For Canadians of a certain age, the sight of Gretzky dabbing at his eyes with a tissue as he wept openly at the press conference when he was traded by Edmonton never will be forgotten.
Best or Worst? Ozzie Albies Signed By the Atlanta Braves Is Still Up in the Air
If you want to keep an eye on one deal that seems destined to land on future lists such as this one, watch what happens with Atlanta Braves infielder Ozzie Albies as his career progresses. The 22-year-old phenom agreed to a seven-year, $35 million deal in spring 2019 — one that Sports Illustrated dubbed “insultingly low.”
But is it? There’s clearly a gamble being taken by Albies — who one day could be worth hundreds of millions on the open market. However, the Braves committed to spending $35 million based on what they saw in one full season and part of another.
Either way, this is one deal that could end up among the worst or the best, and only time will tell. But for Albies, it’s hard to argue with knowing that your worst-case scenario is retiring at 29 having made at least $35 million.
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About the Author
Joel Anderson is a business and finance writer with over a decade of experience writing about the wide world of finance. Based in Los Angeles, he specializes in writing about the financial markets, stocks, macroeconomic concepts and focuses on helping make complex financial concepts digestible for the retail investor.