Ranking Top 10 Trade Deadlines

August 31st, 2020

As we enter July, the pivot month for Major League Baseball, the month in which everyone decides once and for all whether they are buyers or sellers, we could see some of the biggest names in the sport changing teams. Manny Machado, Cole Hamels, Mike Moustakas, Adrián Beltré, Josh Donaldson and maybe even Jacob deGrom -- it could be spectacular.

But then again: This is an annual rite. Looking back throughout history, we're always quivering with anticipation this time of year. Some non-waiver Trade Deadlines have been snoozers; some have turned out to be more electric than any of us could have imagined.

Today, we look at the 10 most active Trade Deadlines in history (or since 1986, when the July 31 Deadline went into effect). Note that we are tracking activity rather than ultimate import; whether these trades ended up changing who won the World Series isn't the measuring stick here. (If so, the most eventful Deadline trade of the past 10 years might have been the Cardinals trading Colby Rasmus for Edwin Jackson and some bullpen arms in 2011; that trade, thought by many as helplessly foolish at the time, simply launched St. Louis into one of the most shocking two months of baseball in recent memory.)

What matters is the activity. And for what it's worth: We're counting the entire month of July as the "Deadline." These are the busiest months.
So, what Deadlines blew everybody up at the time? Here are the top 10.

1. 2008: This might have been the wildest one, including perhaps the three biggest Deadline trades of the past decade -- all in one year. You had Mark Teixeira, a year after the Braves had traded for him, going to the Angels for Casey Kotchman and a Minor Leaguer. You had CC Sabathia, in the midst of dominating for the Indians, going to the surging Brewers at the beginning of the month, where he would pitch so well he almost won the National League Cy Young Award despite only pitching in the league for two months. And perhaps the most fun trade was the Red Sox shipping Manny Ramirez to the Dodgers (for Jason Bay!), turning the place into Mannywood for two months, hitting .396/.489/.743 in 53 games. And we haven't even talked about the two future Hall of Famers who were traded: Ken Griffey Jr. to the White Sox and Ivan Rodriguez to the Yankees. Of course, the Phillies team that won the World Series was the one that traded for Joe Blanton.

2. 1998: The toughest part of the Trade Deadline in the old days was that it didn't pass in the middle of the day, like it does now: It passed at midnight ET. And sometimes, reports about trades didn't come out until a few hours later, which meant you could find yourself waiting until 2 a.m. to find out if anything happened. This is how it went down with perhaps the most famous Deadline deal of all time, when the Astros traded for future Hall of Famer Randy Johnson at the peak of his powers. Johnson had struggled for the Mariners that season, with a 4.33 ERA, but he was dominant for the Astros, going 10-1 with a 1.28 ERA in 11 starts, leading them to the NL Division Series, where they would lose in four games to the Padres. Johnson would sign with the D-backs the following offseason, and the Astros were out Freddy Garcia and Carlos Guillen -- two players who would be huge parts of the Mariners' 116-win season three years later -- in the process. Other players traded at the Deadline that year: Jeff Shaw (for a young Paul Konerko!), Esteban Loaiza, Ellis Burks and Royce Clayton (for Fernando Tatis). But this will forever be the Randy Johnson year.

3. 2004: Talk about a Trade Deadline-changing history. If anything, the biggest name of this Deadline was the Red Sox player who left: Nomar Garciaparra. The Boston icon was shipped to the Cubs, who were on a playoff push of their own, in a four-team deal that ultimately brought the Red Sox back Orlando Cabrera and Doug Mientkiewicz. Garciaparra was obviously the headliner, but, as it turns out, Cabrera and Mientkiewicz -- along with fellow acquisition Dave Roberts -- would end up, somehow, much larger pieces of Red Sox lore. For what it's worth: Garciaparra still got a ring for that 2004 team. Also earlier that month, the Astros brought in Carlos Beltran as a rental. He would be a monster for them that postseason, though he would have to wait another 13 years for his ring to arrive.

4. 2015: The most famous deal from this Deadline was the one that wasn't made, the one that led the Mets' Wilmer Flores -- who thought he had just been traded from the one franchise he'd ever played for -- to weep right out there on the infield at Citi Field. He ended up staying once Carlos Gomez was dealt to Houston rather than New York, and the Mets ultimately upgraded by trading for Yoenis Cespedes, giving up Michael Fulmer, who, for what it's worth, has put up a higher fWAR total since the trade than Cespedes has. This was the strange year that one of the most active teams at the Deadline was the Royals, who brought in Johnny Cueto and Ben Zobrist ... and got a World Series ring for their troubles. Also traded at this Deadline: David Price, Troy Tulowitzki and Cole Hamels.

5. 1997: Even though the White Sox were only 3 1/2 games out of first, they traded Wilson Alvarez, Danny Darwin and Roberto Hernandez to the Giants for six Minor Leaguers in what became known as the "White Flag Trade." Two of those prospects -- Keith Foulke and Bobby Howry -- were large parts of the South Siders' 2000 American League Central championship squad. Don't forget the other big trade from this year, albeit one that didn't affect the pennant chase: The A's traded Mark McGwire to the Cardinals for T.J. Mathews, Blake Stein and Eric Ludwick. McGwire had so much fun with the Cardinals in August and September that he signed with the team that offseason, and we all know what happened after that.

6. 2016: This was the Deadline turned entirely upside down by the Yankees who, for the first (and probably only) time, were sellers. The selloff of their brilliant -- but sort of unnecessary for them at the time -- bullpen led to Andrew Miller heading to the Indians and Aroldis Chapman going to the Cubs, ultimately populating much of that year's World Series. All the Yankees got in return were Gleyber Torres and Clint Frazier.

7. 2002: We're cheating a little bit here, because the trade happened at the end of June, but we're talking about Bartolo Colon, so you'll have to forgive us. Back before he was your favorite meme, Colon was a Cy Young Award winner and the top asset at the Trade Deadline, which is why it was so surprising that the Expos, of all teams, traded for him. They sure paid through the nose for him: Cliff Lee, Brandon Phillips and Grady Sizemore. The Expos also traded for Cliff Floyd and Wilton Guerrero that year, but it didn't work: They didn't make the playoffs, and never would again. Also at this Deadline: Floyd went to Boston (just 19 days after the Expos had acquired him), Kenny Lofton was dealt to the Giants and Scott Rolen's tenure ended with the Phillies after a trade to the Cardinals.

8. 2009: Roy Halladay was the player everyone assumed would be traded, but he stayed put with the Blue Jays. It was seemingly every other star in the game who was shipped out. Victor Martinez went to Boston. Rolen was dealt to Cincinnati. Jarrod Washburn went to Detroit. Jake Peavy was traded to the White Sox. And the biggest one of all was Lee going to Philadelphia, angering Yankees fans who desperately wanted him. Halladay would join him there soon, but, alas, the only title the Phillies team from this era would win had already happened a year earlier.

9. 2017: This Trade Deadline was awfully unappreciated, and we'd probably talk about it forever if Yu Darvish had been better in the World Series. Darvish was the biggest name on Deadline day, going to Los Angeles as the Dodgers made it clear nothing less than the World Series would be acceptable. But other big trades included J.D. Martinez going to the D-backs (where he turned into a monster), Sonny Gray going to the Yankees and Jose Quintana heading from the South Side of Chicago to the North Side.

10. 2000: Just one massive deal here: Curt Schilling, who spent nine years with the Phillies -- even though Philadelphia absolutely is not the city you think of when you think of Curt Schilling -- heading to Arizona for four players, the best of which might have been Travis Lee. This would of course lead to the dominant Johnson-Schilling one-two punch that almost singlehandedly win a World Series a year later. Though the Cardinals will never forget their trade for Will Clark, who would hit .345/.426/.655 for the team, lead them to the playoffs and then retire.