14 Legendary Trades and Free-Agent Signings That Almost Happened

You miss 100 percent of the shots you don’t take. Michael Scott of The Office famously said that, quoting Wayne Gretzky.

And a lot of teams on this list missed a lot of big shots in both trades and free agency. Whether it be general managers having last-second changes of heart, a union meddling, or some other reason, so many trades with legendary potential fell through over the years just as they were about to change history.

It’s always fun to think of what could have been, especially if your team hasn’t had much to cheer about over the last couple of decades. Had some of the trades on this list happened, they would have altered the history of leagues and franchises—turning losers into winners and winners into losers. Heck, the Montreal Expos might still be in existence if one of the trades on this list went down.

So let’s take a look at 14 trades and free agent signings that almost happened. You probably didn’t even know that most of these even existed. And a trigger warning for Raiders fans: They made the list three times. Narrowly missing out on three Hall of Fame quarterbacks.

1983: John Elway is traded to the Raiders.

When Elway was drafted by the Baltimore Colts in 1983, he made it very clear that he would not sign with them. And the Raiders pushed very, very hard to acquire the Stanford QB when teams were calling the Colts about a trade.

The Raiders were looking to acquire the Bears’ No. 6 overall pick in a trade to send to Baltimore as part of a package for Elway—they were reportedly going to trade Howie Long to Chicago to get the pick. According to Elway’s agent, he was told that there was a deal in place for Oakland to get the 6th pick.

The trade never materialized and thus Elway never became a Raider. But this wasn’t the last time the Raiders narrowly missed out on a Hall of Fame quarterback.

1989: Dan Marino is traded to the Raiders.

The Dolphins had just missed the playoffs for the fourth consecutive season in 1989. Hall of Fame coach Don Shula eventually started discussing trade options with Raiders owner Al Davis, and one of these trade options included Marino. The two actually came to an agreement, according to a 2010 piece in the Miami Herald. It did not specify trade details, but said that Davis confirmed that an agreement was made.

The only reason why a trade never happened is that Shula reportedly upped his asking price on Marino twice after verbal agreements had been reached. Eventually, it was too much for even Davis to pull the trigger. And so Marino played the final decade of his career with the Dolphins.

But this wouldn’t be the last time Oakland narrowly missed out on a Hall of Fame quarterback.

1992: Barry Bonds is traded to the Braves.

The Pirates and Braves agreed in principle to a deal ahead of the 1992 season that would have sent (skinny) Barry Bonds to the Braves for outfielder Keith Mitchell, reliever Alejandro Pena, and an undisclosed prospect. This trade would have been a flat-out steal for Atlanta had it gone through, even with Bonds facing free agency at the end of the season.

Then, Pirates manager Jim Leyland found out about the trade agreement and he was livid. Leyland’s objection is the only thing that kept Pittsburgh from trading Bonds, who was named NL MVP that season. Bonds helped lead Pittsburgh to the NLCS, only to lose to the Braves of all teams. He signed with the Giants as a free agent the following year. This would be the last winning season for the Pirates until 2013.

1992: Charles Barkley is traded to the Lakers.

The Sixers and Lakers actually agreed to a deal in 1992 that would send Charles Barkley to Los Angeles in exchange for James Worthy and Elden Campbell. The deal was so close to happening that Barkley went out and had a couple of drinks to celebrate. Per Barkley, from a 2015 SI interview:

“It was going crazy for two weeks so I knew it would come down to Portland, [the] Lakers or Phoenix. So I get a call from my agent one morning and 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.”

It’s unclear when exactly in 1992 this happened, but Barkley said he played well that night. He was eventually traded to the Suns that off-season, where he took the team to the NBA Finals in his first year in Phoenix.

This trade was very close to becoming reality. Back in March 2016, we outlined how one of the most monumental NBA trades of the 90s almost went down:

Kemp remembers how close the trade was to happening. “[Sonics owner Bob] Ackerley called me and told me they weren’t going to make the trade,” Kemp said. “He was telling me people were calling the local radio stations saying they were going to burn down the stadium if I was traded.” Just prior to the 1994 draft, the Sonics told the Bulls the deal was off.

Then in 1997, the Bulls agreed to send Pippen to the Raptors for a rookie draft pick named Tracy McGrady—but it was rejected by Michael Jordan. McGrady later expressed relief that Jordan nixed the trade, saying “I know I wasn’t qualified to fill the shoes of Scottie Pippen at the moment, I’ll tell you that.”

The Bulls’ dynasty could have ended much differently had either of these trades gone through. Speaking of non-trades that preserved dynasties...

1995: Mariano Rivera is traded to the Tigers.

Rivera was very nearly dealt to Detroit in 1995 for another future Yankee: David Wells.

Then-Yankees GM Gene Michael was actively considering trading the future Yankees closer—who was a starting pitcher in Triple-A at the time—to the Tigers in 1995, and Detroit said they would want Rivera in a prospective trade for Wells. The Yankees were actively contending for their first postseason spot in 14 years, and were looking for help in their rotation.

A trade for Wells seemed to make sense. Then, one perfectly timed scouting report prompted Michael to take Rivera off the block. From the New York Daily News:

"I never said yes," Michael said with a chuckle. "And right about that time, Mariano's velocity in the minors jumped to 95-96. I didn't believe it when I saw our report, but I checked it out with scouts from other teams who were there, and it was true. At that point there was no way I was trading him."

Rivera’s velocity had previously only been in the low 90s. Had he not had this velocity uptick, “Enter Sandman” might have been the most popular song in Detroit for almost 20 years.

1996: Reggie Miller signs with the Knicks.

If you’d ask any Knicks fan to name their most hated NBA player of all time, there’s a good chance they’d tell you it’s Miller. I mean, we’re talking about the guy who dropped eight points in nine seconds on them and made his infamous choking gesture at Knicks superfan Spike Lee.

But had he signed with the team in 1996—which was reportedly a strong consideration—he may very well have his name hanging from the rafters at Madison Square Garden today.

Miller considered teaming up with Patrick Ewing in New York to form a superteam to rival the Bulls. These plans ultimately fell through when the Knicks opted to sign Allan Houston instead. Here’s an excerpt from a 1998 New York Daily News article detailing how that all went down:

The Knicks finally signed Houston, while Miller was in Atlanta for the 1996 Olympics. The Indiana player got the news at the U.S. team's hotel, and went whining to U.S. teammate Grant Hill of the Pistons. "Your guy just ruined my plans," Miller told Hill. Nobody really knew what Miller's plans might have been, including Houston. "I didn't care," Houston said yesterday. "I did what was the best situation for me.

Houston was 25 at the time while Miller was 31, so Houston was seen as having a bigger upside. The Knicks’ shootin guard did indeed make a major impact in New York—before knee injuries prematurely derailed his career.

Still though, the thought of Miller in a Knicks uniform is a strange one. It would have been curious to see whether an Ewing-Miller Knicks squad could have knocked the Bulls off in the playoffs.

2000: Tim Duncan signs with the Magic.

It’s hard to imagine Tim Duncan wearing anything but a Spurs jersey. This almost wasn’t the case though, because the Magic were trying to form a superteam.

Duncan was a free agent in 2000, as were Tracy McGrady and Grant Hill. The latter two, obviously, ended up with the Magic, and Duncan was very close to leaving by his own account. Said Gregg Popovich of Duncan’s 2000 free agency: "It was hell. You get close to a player and you don't want to see him leave. I never let myself believe he was going to stay. I was just getting myself prepared, for sanity reasons. It's no fun.”

Duncan eventually signed a four-year, $45.9 million contract (chump change in today’s NBA) to stay in San Antonio. And while the prospects of a Duncan-McGrady-Hill trio are fun to think about, it’s safe to say that Duncan made the right call in staying with the Spurs.

2000: Albert Pujols is traded to the Expos.

Looking for young pitching, the Cardinals were able to acquire journeymen Dustin Hermanson and Steve Kline from the Expos. They were to give in return reliever Brett Reames and one of two players: Fernando Tatis or Albert Pujols.

The Cardinals were reportedly conflicted as to include Tatis or Pujols in the trade. Comparing these two seems laughable now, but Tatis was an established major leaguer—and just one year removed from a 34-homer, 107-RBI season in 1999. Pujols hadn’t yet played in the majors. Tatis was ultimately the one who was traded, and the rest is history.

Had the Cardinals included Pujols in the deal though, the Expos might still be in existence. Maybe having a lineup that included Pujols and Vlad Guerrero would push the team into the postseason—or at least kept the team competitive—thereby revitalizing interest in the Expos and helping the team secure a new stadium. But it was not to be…

2004: Alex Rodriguez is traded to the Red Sox.

ESPN did a fantastic “30 For 30” short on this non-trade that’s definitely worth a watch. Basically, the proposed trade was a three-team deal with the Red Sox, Rangers, and White Sox. The Red Sox would receive Alex Rodriguez and Magglio Ordonez, the Rangers would receive Manny Ramirez and Jon Lester, and the White Sox would receive Nomar Garciaparra and Scott Williamson. It easily would have been the most star-studded trade in baseball history, and perhaps in the history of sports.

The trade fell apart because it would have included a pay cut for Rodriguez—which he would have agreed to—but the MLB Players’ Association would not. They felt it would create a precedent of players agreeing to pay cuts to get traded.

It would be curious to see if the Red Sox would have still won any of (or more than) their three 21st-century championships had this trade gone down. The Rangers certainly would have received a much better return for this deal then they received from the Yankees when they shipped A-Rod to New York. All Texas got was Alfonso Soriano and Joaquin Arias in the final A-Rod deal.

Oh, and while we’re on the subject of near trades, the Rangers had to chose between two Yankees prospects in the A-Rod deal: Arias or Robinson Cano. They took Arias.

2004: Terrell Owens is traded to the Ravens.

This was another trade that was agreed to, but never officially went through. The Ravens were to send a second-round pick to the 49ers for T.O., who refused to show up for a physical in Baltimore. Owens was ultimately traded to the Eagles, the team he wanted to play for. Since this trade never went through, the Ravens settled with the 49ers and received a fifth-round pick as compensation for the trade that never was.

That season, Owens again drew the ire of Baltimore fans when he impersonated Ray Lewis’ classic dance after scoring a touchdown against the Ravens:

2006: Drew Brees signs with the Dolphins.

It’s very rare that a team would allow a franchise quarterback-type to hit free agency. Heck, it’s rare to find even a solid starting quarterback that hits the open market these days. But after Brees suffered a torn labrum on the last day of the 2005 season, the Chargers offered Brees an incentive-heavy deal that he passed up on in hopes of finding franchise QB-type money in free agency.

The two teams that were most interested in Brees that offseason were the Saints and the Dolphins. Miami, however, opted not to sign Brees after he failed a physical with the team, according to then-Dolphins coach Nick Saban. The Dolphins ended up trading for Daunte Culpepper instead, which prompted Brees to make things official with the Saints. The fortunes of these two franchises went in entirely different directions, with Brees carrying New Orleans to its first Super Bowl title and five playoff appearances.

Saban also said that had Brees signed with Miami, he might still be coaching in the NFL. So a lot of Alabama fans are probably very happy that Brees signed with the Saints.

2007: Aaron Rodgers is traded to the Raiders for Randy Moss.

This one may have been more of a rumor than anything else. But it was apparently serious enough that Deadspin did an article on the matter in 2007 titled “We Repeat: Please Let the Moss Trade Happen,” in which it said that a Moss-Rodgers trade was imminent, citing a Boston Herald report. At this time, Rodgers was Brett Favre’s backup, and the Packers lacked an elite receiver.

According to former Packers exec Andrew Brandt, Moss was indeed almost a Packer. From a 2012 ESPN article:

In 2007, the Raiders made Randy Moss available. We were interested provided we could agree on trade terms and compensation. The Patriots were interested, too.







Moss demanded a one-year deal so he could hit the market after the season and recoup some lost value, but we insisted on a two-year deal. We did not want to be a temporary stop for him before he made another big contract elsewhere. When New England relented on the one-year term, Moss was a Patriot.

The Pats eventually acquired Moss for a fourth-round pick, so it seems unlikely that it would have required a former first-rounder like Rodgers to finish the deal. Green Bay made a huge mistake by not giving in to Moss’ demands; the Packers made it all the way to the NFC Championship game in 2007 without Moss. Imagine what they could have done with Moss.

Kobe Bryant to the Wizards/Clippers/Bulls.

It didn’t always look like Bryant would stick with the Lakers for 20 years. In fact, there were two instances where the Black Mamba nearly left town for other teams.

Kobe, who was a free agent for the first time in 2004, initially hoped to go to the Wizards to play under Michael Jordan. Kobe, an admirer of Jordan, had these dreams dashed when Jordan left the Wizards in 2003. So while a Kobe-Jordan combo may not have been practical or a real possibility, it’s cool to think that the two could have actually been teammates at one point.

When Kobe actually did hit free agency that year, he said he was “very close” to signing with the Clippers. The team was considering a move to Anaheim at the time, which Bryant found to be intriguing, and his feud with Shaquille O’Neal had reached a boiling point. Bryant ended up re-signing with the team the day after Shaq was traded to the Heat.

A couple of years later in 2007, Bryant demanded a trade after a few lackluster Lakers seasons. And the Bulls were his personal top choice to land. But the Lakers were adamant in receiving a young Luol Deng in any trade with the Lakers, and Kobe wanted to play with Deng. This situation is reportedly what killed the deal.

During this time, the Lakers also reportedly offered Bryant to the Pistons for a package that included Rip Hamilton, Tayshaun Prince, and draft picks. But Kobe had no interest in playing in Detroit, so this was never going to happen.