The Greatest Sports Deals Never Made

If these blockbuster moves had happened, the sports world would look a lot different.

The Greatest Sports Deals Never Made

Golden State Warriors guard Klay Thompson, right, drives to the basket against Chicago Bulls forward Justin Holiday, left, during a 2018 NBA basketball game in Chicago.

In many ways, sports fandom has become more about the transaction than the on-field or on-court results. Checking the rumor mill has become an integral part to being a fan. It’s what feeds the daily fodder of the sports media news cycle. It piques interest in the months without competition. It drives the narrative of "who’s next?" in sports.

The transaction has become the most interesting thing about sports. When and how this changed is up for discussion, perhaps a natural evolution accelerated by the wild success of the sports debate show. What is clear, though, is the public loves the rumor mill. Without it, there would be much less to debate.

The move that doesn’t get done is often more interesting than the one that did, which is why these near transactions are so tantalizing.

Alex Rodriguez, Red Sox Legend?

Texas Rangers shortstop Alex Rodriguez waves to fans at Safeco Field in Seattle before a game against the Mariners on April 16, 2001, in Seattle. The appearance in Seattle was Rodriguez's first since leaving the M's to sign with the Rangers.

Teams involved: Boston Red Sox, Chicago White Sox, Texas Rangers

Players moving: Alex Rodriguez, Nomar Garciaparra, Jon Lester, Magglio Ordonez, Manny Ramirez

The move that wasn’t: Red Sox acquire Ordonez, Rodriguez and prospect Brandon McCarthy; White Sox acquire Garciaparra and Scott Williamson; Rangers acquire Ramirez and Lester

What could have been: Man, oh man, what could have been. The past two decades of Red Sox success mostly hinged upon the MLBPA rejecting a restructuring of the then-record $250 million contract Alex Rodriguez signed with the Rangers. A rare instance where all teams agreed, the players were notified, the league signed off and the union said, "Nope!"

The Red Sox were fed up with Manny Ramirez and his antics at the time, even placing him on open waivers early in the 2003 offseason, hoping someone would bite and take the final five years of his sizable contract off their hands for free. The luster of Nomar Garciaparra had worn off, as his body began to break down, and the combo of Magglio Ordonez and Rodriguez would have more than sufficiently replaced their talent.

This move that nearly happened in December 2003 would have no doubt massively affected the future of the entire league. That is not just in reference to the Red Sox acquiring an all-time great in exchange for two of their own, but moving a 20-year old Lester potentially negates two future World Series championships for Boston.

As it turned out, the Yankees played spoiler (or so they thought at the time) and swept in, flexing their financial muscle to acquire Rodriguez. While the Yankees did win a championship with Rodriguez six years later, the lack of a move ushered in an era of unprecedented success in Boston, which dealt Garciaparra to shore up their infield at the 2004 trade deadline, bringing the Red Sox their first title in 86 years.

Duncan Goes to Disney World

San Antonio Spurs power forward Tim Duncan considered wearing an Orlando Magic uniform.

Teams involved: San Antonio Spurs, Orlando Magic

Players moving: Tim Duncan, Grant Hill, Tracy McGrady

The move that wasn’t: Duncan signs with Orlando as free agent, joining Hill and McGrady

What could have been: Another often-referenced, league-altering move nearly came together in the summer of 2000. Before Chris Bosh, Dwyane Wade and LeBron James took their talents to South Beach, the trio of Grant Hill, Tracy McGrady and Tim Duncan discussed building a big three of their own in another Florida city.

Back in the days before restricted free agency, players became unrestricted free agents following their rookie contracts, and Duncan was exploring his options. Hill, who started his career with the Detroit Pistons, and McGrady, who began with the Toronto Raptors, were the first two players to sign with the Magic. They were recruiting Duncan to join them.

"It will be unfair to the league if all three of us come here," McGrady said at the time. "We have the East. We'll be playing the Lakers for years."

Duncan and Gregg Popovich later gave even more credence to this nearly becoming a reality. It’s especially intriguing given the departure of Shaquille O’Neal to Los Angeles just a few years earlier, creating a cross-coast rivalry.

Would the added ability of Duncan been enough to keep Hill off the injury list, with his usage decreasing? Would his leadership have been the same without learning under the Popovich tree for the next decade?

The Spurs would not have been able to maintain their level of consistency without Duncan. That much is clear. San Antonio struggled to attract free agents even with Duncan, and with him in Orlando, the Spurs may not even have a team right now had the future not been prosperous.

As for the Magic, there is no certainty given Hill’s injury history, but even Duncan and McGrady together would have been an interesting dynamic to watch, mirroring Kobe and Shaq in Los Angeles.

Never More, Never More

Teams involved: San Francisco 49ers, Baltimore Ravens, Philadelphia Eagles

Players moving: Terrell Owens

The move that wasn’t: Ravens acquire Owens; 49ers acquire Ravens’ second-round draft pick

What could have been: One of many in the string of Terrell Owens’ public-relations blowups came in 2004, when a disgruntled Owens was fed up with the mediocrity of the 49ers teams since the departure of Jerry Rice and Steve Young. A love-hate relationship with Jeff Garcia and clashes with the coaching staff led to Owens demanding a trade.

He got what he wanted, except not quite. The 49ers agreed to ship Owens to the Baltimore Ravens in exchange for a second-round pick, which accomplished two goals for the 49ers:

It got Owens off the team.
It kept Owens out of the conference.

T.O. already had begun negotiations with the Philadelphia Eagles at the time and had planned to sign there in free agency. However, Owen’s agent failed to file the paperwork, which meant the 49ers still had his rights. Owens had no time for the 49ers’ goals, or the Ravens, as it turned out, and flat out refused to show up to the Ravens facilities to take the necessary physical.

With no recourse, the Ravens dealt Owens to Philly for some chump change and got back their second-rounder. Without that year with the Eagles, the legend of Owens as both an on-field stud and a locker-room cancer might have been much less prevalent.

Clipper Kobe

Kobe Bryant and Cuttino Mobley — Los Angeles Lakers guard Kobe Bryant, left, chats with Los Angeles Clippers guard Cuttino Mobley during a 2007 NBA basketball game in Los Angeles.

Teams involved: Los Angeles Lakers, Los Angeles Clippers

Players moving: Kobe Bryant

The move that wasn’t: Bryant signs with Clippers as a free agent

What could have been: The mid-aughts were a tumultuous time in Laker land. Just a year removed from appearing as an unbeatable dynasty with the all-time great combination of size and skill from Kobe and Shaquille O’Neal, the Lakers' future was thrown into disarray.

Bryant became fed up with the in-fighting between him and O’Neal, and despite their success as a tandem, essentially gave the Lakers an ultimatum that there were two ways they could go. In the summer of 2004, Bryant hit free agency for the first time, and entertained the idea of becoming the savior for a Clippers franchise that was exploring a move to Anaheim at the time.

Before talks got truly serious, the Lakers shipped Shaq to Miami, and Byrant re-upped with the purple and gold the next day. It’s not unfair to question how sincere Bryant’s meetings with the Clippers were, but had the Lakers decided to stick with the big man, it might be a different color jersey hanging up at Staples Center.

¡Viva Ronaldo!

Teams involved: Arsenal FC, Manchester United

Players moving: Cristiano Ronaldo

The move that wasn’t: Ronaldo signs with Arsenal

What could have been: The ascendency of Cristiano Ronaldo was meteoric, but definitely unsurprising to those who followed his youth career. When Ronaldo was an 18-year-old and a highly sought-after forward for Sporting Lisbon, he landed on Manchester United as his home, playing six seasons with the Red Devils.

However, had it not been for some financial restraints, Ronaldo’s Premier League highlight reel would have him donning an Arsenal kit instead.

According to an Arsenal scout, and head man Arsene Wenger himself, Ronaldo was in the Arsenal crosshairs prior to signing with Manchester United, but before the team could scrape together the funds, he was scooped up by the Red Devils following a breakout performance against them.

Ronaldo grew to become the best player in the world at the end of his six seasons in Manchester, the last three of which ended in Premier League titles. Those league championships might have belonged to Arsenal otherwise, and the transfer fee of 60 million euros that Man U used to set themselves up for future success also may have reaped benefits down the line for Arsenal.

Miami Feels the Brees

Teams involved: Miami Dolphins, New Orleans Saints

Players moving: Drew Brees, Daunte Culpepper

The move that wasn’t: Dolphins sign Brees as free agent

What could have been: Another one from the "what if …" Hall of Fame. Drew Brees was about as close as you could come to being the next quarterback of the Miami Dolphins when he was a free agent in 2006.

Coming off his final season as a San Diego Charger, Brees severly injured his shoulder in the team’s final game, and the Chargers opted to go for the future with Philip Rivers, who had been waiting in the wings, letting Brees go to free agency.

Brees initially met with the Dolphins and was zeroing in on a deal with the ‘Phins, but Miami’s doctors did not think the shoulder was stable enough to hold up long term and failed his physical evaluation. Had he been cleared, Brees might have engineered the 21st century version of Dan Marino’s Dolphins, with weapons Ronnie Brown and Rickie Williams flanking him in the shotgun.

As it turned out, the Dolphins opted for Daunte Culpepper, who had recently shredded his knee. Culpepper never returned to his MVP-caliber form, while Brees blossomed into an all-time great. Had the Miami doctors not been as cautious, New Orleans might not even have a team, let alone a Super Bowl trophy.

Big Shot Sean?

Teams involved: Houston Rockets, Detroit Pistons

Players moving: Robert Horry, Matt Bullard, Sean Elliott

The move that wasn’t: Rockets trade Horry and Bullard to Pistons for Elliot

What could have been: During the 1993-94 NBA season, the Rockets were enjoying one of the best seasons in franchise history and wanted to seize the moment. They had a deal in place to send a couple of their young players to Detroit for Sean Elliott, an All-Star scorer with San Antonio in the previous 1992-93 season.

What happened next was a huge shocker, as the deal was nixed following the discovery of Elliott’s kidney condition in the pre-trade physical. Elliott later would need a transplant and returned to San Antonio after the trade rumors did irreparable damages to his relationship with Detroit. But Robert Horry went on to earn the moniker of "Big Shot Bob" or "Big Shot Rob" for clutch buckets in the Rockets’ championship run.

The trade jarred something in Horry immediately, "I came back with a [forget]-you attitude. I said, 'I'm probably the only player in the history of basketball that got traded for not shooting the ball.' "

That new attitude propelled him to great heights in Houston and later Los Angeles (Lakers) and San Antonio, but had the trade held up, he might have become a top scoring option for the Pistons, which could have potentially disturbed his future as a top-notch role player. As players such as Reggie Jackson, Dwight Howard and others have shown, once you are the top guy, it’s tough to get that out of your head.

Thankfully for Horry, and the Rockets, the trade never happened, and Houston has two banners hanging in the rafters.

A Stern Rejection

Teams involved: New Orleans Hornets, Los Angeles Lakers, Houston Rockets

Players moving: Chris Paul, Pau Gasol, Lamar Odom, Luis Scola, Goran Dragic, Kevin Martin

The move that wasn’t: Lakers acquire Paul; Hornets acquire Odom, Scola, Dragic, Martin and Lakers first-round pick; Rockets acquire Gasol

What could have been: The New Orleans franchise was in a state of flux in 2011. The team was without an owner, and the league stepped in to take control of the franchise. Fed up with mediocrity, star player Chris Paul looked to be traded and had his sights set on the West Coast

In one of the most controversial and debated moves in NBA history, David Stern (who technically owned the team) vetoed a trade that would have sent Paul to the Lakers for a package that would have landed the Hornets a package of Martin, Scola, Odom, Dragic and a first-round pick, while Gasol would have gone to Houston.

The machinations of this "what if" have inescapable reverberations that would have changed the entire future of the league.

It would have instantly turned the Lakers back into title contenders, with a core of Kobe, Paul and emerging big man Andrew Bynum. The Rockets, who had Kyle Lowry and a rookie Chandler Parsons, could have become a competitive Spurs-like squad based on ball movement and passing. The Hornets, who eventually shipped Paul to the Clippers for a much less desirable package, could have stayed competitive with four established NBA vets and the first-rounder.

This also means the Dwight-Nash-Kobe threesome never happens, neither does Lob City, or maybe even the James Harden trade.

Just Not Enough for the Celtics

Teams involved: Miami Heat, Charlotte Hornets, Boston Celtics

Players moving: Justise Winslow

The move that wasn’t: Celtics trade four first-round picks, two second-round picks to Hornets for No. 9 pick

What could have been: Danny Ainge is a genius. The Celtics currently flaunt a starting five of All-Star-caliber players and are one of the favorites to win the Eastern Conference after a strategically savvy rebuild.

Ainge also nearly messed up the entire thing when he offered a king’s ransom for a falling Justise Winslow on draft night in 2015. The only thing in Ainge’s way was the ineptitude of Hornets owner Michael Jordan, who was so set on getting Frank Kaminski at No. 9, he rebuffed the Celtics' offer of six draft picks.

The Heat took Winslow at No. 10, and the Celtics used the bulk of those picks on what look to be future and current stars and a cast of solid NBA players. Could they have been massively protected? Sure, but that type of haul for Frank Kaminski still would be nearly impossible to turn down.

Put Winslow on the Celtics and take away Jaylen Brown, Jayson Tatum and Kyrie Irving (due to the picks involved in trading for him). What’s left for the Cs? Hot garbage. And what happens to those players? Impossible to know the answer to that, but a potential budding future Celtics dynasty would either not exist or look very, very different.

Motown Mariano

Teams involved: Detroit Tigers, New York Yankees

Players moving: Mariano Rivera, David Wells

The move that wasn’t: Tigers trade Wells to Yankees for a package including Rivera

What could have been: In 1995, two of the biggest heroes in modern Yankees history were nearly swapped for one another before either of them earned their pinstripes in New York. Wells, a hard-throwing lefty for the Tigers was targeted by the Yanks, when then-general manager Gene Michael was looking to make a splash to acquire the left-hander.

"I really liked David Wells, and the Tigers gave me a list of eight of our guys who they were interested in," Michael said. "Mariano’s name was one of them, even though he really wasn’t a top prospect."

Rivera blossomed at the right time in the minors, prompting Michael to remove his name from the list shortly thereafter, and Wells ended up in Cincinnati with the Reds.

Had this swap originally gone down, Rivera never flourishes in the closer role for the 1990s dynasty, and never teams with Wells in pinstripes. Rivera's late-inning abilities would have made him a hot piece for the Tigers to deal to a contender in need, and Rivera could have had a much different career with a few different stops.

Premature Barkley Binge

Teams involved: Los Angeles Lakers, Phoenix Suns, Philadelphia 76ers

Players moving: Charles Barkley

The move that wasn’t: Barkley traded to the Lakers from the 76ers for James Worthy

What could have been: This is a rare instance of what happened being more interesting than what could have. Charles Barkley’s name had been on the trade block for weeks in 1992, and he knew he was going somewhere. He just wasn’t sure if it would be Phoenix, Portland or Los Angeles.

Barkley got a call from his agent the morning before a 76ers game with apparently breaking news, "He said, 'Philly has traded you to the Lakers.' " So I went to lunch and started drinking. I'm f---ing so excited that I am going to the Lakers. Three hours later I get a f---ing phone call from my agent saying that the Sixers backed out of the deal. I said, 'Oh, s--t, I'm feeling pretty good right now.' So I went out and played that night."

The search continues for the box score from this now infamous "Drunk Charles" game.

Far beyond the basketball ramifications of a 1992 Lakers team that had just lost Magic Johnson to his shocking HIV announcement, the idea of Barkley in L.A. is absolutely wild off the court. However, Barkley ended up in the desert just east and flourished in Phoenix as a Sun. Still, the thought of Barkley in purple and gold remains a fascinating idea.

No Love for Klay

Teams involved: Minnesota Timberwolves, Golden State Warriors

Players moving: Klay Thompson, Kevin Love

The move that wasn’t: Warriors trade Thompson to Timberwolves for Love

What could have been: In the summer of 2014, Warriors general manager Bob Myers felt he needed to make a big splash. Stephen Curry had just backed up his first All-Star season with another one, and the Warriors were on the verge of busting out with their young superstar. However, Myers felt the team was a move away, and the Timberwolves were dangling their own disgruntled superstar in a trade.

What makes this hypothetical so interesting is twofold:

The trade was signed off on by both parties.
The trade drastically changes the last five years of NBA history.

Everyone was ready to sign on the dotted line, but Warriors adviser Jerry West refused to sign off, causing hesitation and the eventual crumbling of this blockbuster. Love ended up in Cleveland, instantly becoming the foe to the Warriors, and Thompson emerged into a crucial member of the Warriors dynasty.

The idea of a pick-and-roll between peak Love and Curry is a basketball purist’s dream, while many wonder how effective Thompson would be as the focal point of the offense. An even bigger questions is how does this change LeBron James' decision to return to Cleveland, as Love becoming part of the team seemed destined from the exclusion of Andrew Wiggins in LeBron's Lee Jenkins letter.

Brave Barry

Teams involved: Pittsburgh Pirates, Atlanta Braves

Players moving: Barry Bonds

The move that wasn’t: Braves trade Keith Mitchell and prospects to Pirates for Bonds

What could have been: In 1992, Barry Bonds’ approaching free agency loomed large for the Pirates. The team had enjoyed plenty of success with Bonds as their cornerstone, but they couldn’t pay him what he was worth and were desperate to get an asset for Bonds prior to his exit.

Pirates manager Jim Leyland caught wind of this agreed swap and convinced the franchise to hold on to their perennial MVP candidate. The Pirates wound up losing to the Braves in the NLCS in a dramatic play at the plate, where Bonds failed to gun down the winning run at the plate.

Had Bonds been a Brave, that could have put them over the hump. The team lost in six games in the World Series to a very talented Toronto squad, but the added thump and speed of Bonds in the lineup could mean an extra MLB championship banner for Atlanta.

Mariota to Philly

Teams involved: Philadelphia Eagles, Tennessee Titans

Players moving: Marcus Mariota, Sam Bradford

The move that wasn’t: Eagles trade Bradford, Fletcher Cox, two first-round picks, second-round pick to Titans for No. 2 pick in the 2015 draft

What could have been: Chip Kelly was entering his third year as head coach of the Eagles, and despite shooing off many of the big name players on the squad, he had seen some success with his system in the pros. What he lacked was the man to run that system.

The former Oregon coach reportedly was prepared to sell the farm for the rights to draft Mariota, offering a pair of solid pros and a trio of desirable draft picks, but the Titans held their resolve and drafted the leader of their franchise in the Heisman winner.

This move at the very least probably buys Kelly some more time in Philadelphia, wiping out that most recent Super Bowl title and putting Carson Wentz in another team’s jersey. It also could have worked out. Kelly’s time in the NFL, while hot and cold, was largely a strategic success missing the right chess pieces.

Kelly and Mariota could have extended their success as Ducks into the pros, but the Titans liked him too much to give him up.

Gerrard Feeling Blue

Teams involved - Liverpool, Chelsea

Players moving: Steven Gerrard

The move that wasn’t: Gerrard transferred to Chelsea

What could have been: One of the names most synonymous with the Liverpool red nearly diverged from that path to become one of the club’s biggest villains ever. In July 2005, Gerrard handed in a transfer request to the Liverpool brass, fed up with the club’s penny-pinching. Fans reacted poorly, lashing out against the man who just months earlier had one of the most incredible performances in Champions League history.

Chelsea made a large bid, north of 32 million pounds (now $40.7 million) for the then 25-year-old Gerrard, and for a moment, Gerrard looked to be demanding to head there. However, when Liverpool hired manager Rafa Benitez, Gerrard quickly changed his tune, bonding with the new head man and sticking with Liverpool through the next decade.

Had the Benitez-Gerrard relationship not flourished so quickly, Gerrard would have gone down as one of the most vilified names in sports, similar to when LeBron James joined Miami.