The Five Greatest Trade Deadlines in Baseball History

By The Common Man

The trade deadline looms on Sunday, and we’ve already seen some rather large deals. Beltran’s gone, Rasmus has been chained to a chair and put on a train out of Springfield…er, St. Louis, and can you believe somebody actually wanted Kosuke Fukudome? Most of the action has been late this year, with so many teams seeing that they have shots at the postseason and with what seems like relatively few truly valuable commodities readily available. It’s made TCM wonder how this deadline compares to deadlines of the past.

The trade deadline, as we know it, is actually not terribly old. Brian Cronin, of The Fabulous Forum, traces the origin of the trade deadline to the 1920s, when owners banded together to stop Harry Frazee from trading players to the Yankees in the middle of a pennant race. They set the trade deadline at June 15, which would be early enough, conceivably, that most teams would still have theoretical shots at the postseason, and actual contenders might still not have given up on some of their weakest players turning it around. As such, deadline activity was relatively light for much of the 20th century.

The June 15 deadline stayed in place until 1985, when baseball’s labor agreement was set to expire yet again, and players were threatening the second mid-season strike of the decade. In August, the owners and players came to an agreement (which then, of course, the owners proceeded to ignore and collude against the players). As part of that peace accord, owners and players agreed to move the trade deadline to July 31, while setting a separate deadline, contingent on players passing through waivers, on August 31. There was almost no coverage or analysis of this provision in the media at that time.

The next year saw a great deal of confusion as teams tried to adapt to the new rules. The Braves made two separate trades on the same day with the Blue Jays to acquire veterans, since they were just 3.5 back in the NL West. The Padres provided an avenue for the Yankees to ship Ed Whitson out of New York. The White Sox traded Bobby Bonilla to the Pirates for young pitcher Jose DeLeon. The last big trade of that summer was on July 30, when the White Sox sent Ron Kittle, Joel Skinner, and Wayne Tolleson to the Yankees for Ron Hassey and two prospects. Some of the most interesting action, however, took place after the deadline, as teams were not gaming the waiver system well. Perfectly useful players like Mike Heath, Danny Darwin, Dave Henderson, and Spike Owen made it through with ease. The only snag came when the Red Sox tried to acquire Henderson and Owen for four players, two of whom they forgot they had to send through waivers. They were considered PTBNL, and sent a few days later.

Still, deals remained the exception rather than the rule for several years. The playoff structure, with two division winners and no wild card teams, limited the number of teams who saw themselves as contenders, and teams generally hovered between 10-15 deals in July through 1993. The strike ruined the trade deadline in 1994, but the partitioning of the league into six divisions, and the addition of the wild card proved to be a boon for deadline activity. Consider the following graph:

Click to embiggen

As you can see, activity jumped sharply in 1995, and then again in 2000. There is, obviously, still a lot of volatility in the market, given that some years have more competitive races than others, but the trend is clear that teams have taken much greater advantage of the trade deadline since the start of the 21st century, establishing a new paradigm at the end of July that has become part of the fabric of the game. This has coincided with the rise of social media and 24 hour news cycles, allowing fans to be more engaged at the deadline than ever, driving clicks and money to media outlets and Major League Baseball. In short, there’s almost no chance for this paradigm to change any time soon. More deadline activity is good for baseball.

In looking back at all the deadlines, what strikes The Common Man most is how many of these deals don’t pan out. Players acquired for stretch drives bomb or prospects don’t pan out. There are so many guys exchanged and relatively deals work out as intended. But with that said, here are the 5 best deadlines since the trade deadline was pushed back to July 31:

5) 2003

The month of July got off to a quick start in 2003, as future Hall of Famer Roberto Alomar was traded to by* the Mets on the first for three players, including the highly-regarded Royce Ring. The Sox were not giving up, given they were only three games back of the Kansas City Royals, so they traded three prospects of their own (including Frank Francisco) to the Rangers for Jurassic Carl Everett. The Rangers were entirely out of it and were in full-on sell mode, and picked up three prospects from the Marlins for closer and future attempted-murderer Ugueth Urbina. One of those prospects was Adrian Gonzalez, which is clearly more than an attempted-murderer should be worth, but there you go.

The Mets continued to add pieces in the middle of the month, picking up Jeromy Burnitz from the dodgers on the 14th, for three prospects that never panned out. All of this was highly hilarious, since the Mets had started July 36-46, and didn’t improve at all as the month dragged on.* The did, however, sell off Armando Benitez to the Yankees for three minor leaguers two days later.

(Ed. Note: As a commenter points out below, The Common Man somehow transposed these trades in his head so that he thought the Mets were acquiring both Burnitz and Alomar.  He should have realized that didn’t make sense.  TCM apologizes to Steve Phillips, who was the GM at the time, or ever believing he could ever have such a terrible lapse in judgment.)
The Twins, on the other hand, were in the thick of the AL Central race, and traded Bobby Kielty to the Blue Jays for Shannon Stewart, who proceeded to finish .322/.384/.470 and pick up some ridiculously misplaced MVP votes, finishing 4th in the AL. The Cubs, teetering on the edge of relevance, managed to convince the Pirates to take a deal centered around Bobby Hill for Kenny Lofton and Aramis Ramirez. The deal worked out horribly for the Pirates, but the Cubs caught fire and won the NL Central, falling just a Steve Bartman shy of the World Series.

4) 2000

July of 2000 was one of the most active deadlines in baseball history, and started out being all about the pitching. The Braves picked up Andy Ashby for Bruce Chen and change. The Yankees traded for Denny Neagle from the Res for four players, including mega-busts Drew Henson and Ed Yarnall. The Rangers dealt Esteban Loaiza for Michael Young and more. The Diamondbacks landed Curt Schilling from the Phillies for a four-player package that included Omar Daal, Nelson Figueroa, Travis Lee and Vincente Padilla, all of who were or turned into legitimate Major Leaguers. And the Indians traded a package fo four players to the Brewers that included Richie Sexson and Marco Scutaro for Jason Bere, Bob Wickman, and Steve Woodard.

Teams began searching for bats much later. The Red Sox brought in Mike Lansing and Rolando Arrojo from Colorado in a failed bid to shore up their wild card hopes. The Orioles unloaded Mike Bordick to the Mets for four players, one of whom was Melvin Mora. The White Sox upgraded at DH and catcher by getting Harold Baines and Charles Johnson from the Orioles for four players, of whom only Brook Fordyce ever did anything. Meahwhile, the O’s traded BJ Surhoff to Atlanta for three players who never panned out.

The best deal, however, was made by the Cardinals, who were desperate for help with Mark McGwire out for the season. They got Baltimore to trade Will Clark to them for a corner infield prospect who would have just a .262 career on base percentage in 221 big league plate appearances. Clark would hit .345/.426/.655 with 12 homers for them in 197 plate appearances, helping them win the NL Central and reach the NLCS, and retire immediately following the season.

3) 2009

As of July 1, 2009, nineteen teams were within 5 games of their division lead. But aside for Jeff Francoeur going to the Mets for Ryan Church, nothing Earth shattering happened until July 24, when the A’s sent Matt Holliday to St. Louis for three players, including Brett Wallace. Holliday was a monster for the Cardinals, hitting .353/.419/.604 for the last two months and providing good defense in left field. On the 29th, Cleveland launched Cliff Lee’s odyssey around the MLB by dealing him and Ben Francisco to the Phillies for Carlos Carrasco, Jason Donald, Lou Marson, and Jason Knapp. The Giants picked up Freddy Sanchez for Tim Alderson that same day, and the Pirates got Ronny Cedeno and three other players from the Mariners for Jack Wilson and Ian Snell.

The 31st also saw a flurry of big deals, with a lot of players changing hands. The Red Sox traded three players, including Justin Masterson to the Indians for Victor Martinez. The Sox also sent Adam LaRoche (who they had traded for earlier that July) to the Braves for Casey Kotchman. The Reds acquired Scott Rolen for Edwin Encarnacion and Zach Stewart. The Twins shored up their shortstop position with Orlando Cabera. And the Padres acquired four pitchers, including Clayton Richards, from the White Sox for Jake Peavy. 2009 may not have seen the most deals in July, but it definitely seems to have seen the most big deals that actually affected the pennant races.

2) 1989

Sometimes it’s not quantity, but quality. July of 1989 was the first big trade deadline where teams upgraded wildly. The Braves got three prospects for Zane Smith to start things off. Then the Reds traded Kal Daniels and Lenny Harris to the Dodgers for Mariano Duncan and Tim Leary. The Yankees shipped Mike Pagliarulo to the Padres for Walt Terrell.


But two trades truly ruled the month that summer, both of them coming out of the AL West. In the first, the White Sox were 43-60, 20.5 games back of the Angels when they decided to unburden themselves of Harold Baines and Fred Manrique. The Rangers, who were 8 back at the time, got back another 2B, Scott Fletcher, a young left-handed pitcher named Wilson Alvarez, who would pitch a no-hitter at 21, and anchor the Sox rotation for more than four years while Jeff Torborg Gene LaMont pitched his arm off, and a skinny little Dominican outfielder named Sammy Sosa, who would soon fade into obscurity after eventually being traded for George Bell.


The other deal happened just before the deadline, as the struggling Twins sent reigning Cy Young Award winner Frank Viola to the Mets for five pitchers, including Rick Aguilera and Kevin Tapani, both of whom Minnesota would use to great success two years later when they won the World Series. The heartbroken Common Man was stunned when he heard the news, and created a shrine to Frankie “Sweet Music”. Hopefull, the prospects brought back in 2011’s deadline deals will make other 10 year olds forget their idols just as easily.


1) 1998

Things started slowly in 1998. The first salvo actually came from the Dodgers, who were 7 back in the Wild Card race when they traded for Jeff Shaw, giving up prospects Paul Konerko and Dennys Reyes. Shaw was great, but the Dodgers still finished well back of the pack.

By the middle of the month, the Rangers were a half-game behind the Angels and looking to shore up their rotation, and traded Warren Morris and Todd Van Poppel to the Pirates to pick up Esteban Loaiza. The trade was a disappointment, as Morris would finish 1999 3rd in the Rookie of the Year voting, while Loaiza put up a 5.90 ERA in 14 starts over the rest of ’98. But the Rangers won the AL West anyway.

The Indians had a huge lead in the AL Central, but were having problems with their bullpen. So they dealt Shawon Dunstan and Jose Mesa to San Francisco for Steve Reed, and picked up Doug Jones from the Brewers for Eric Plunk. The Giants also used the deadline to pick up Joe Carter from the Orioles. Joe was rejuvenated by the Bay, and put up a .884 OPS over the rest of 1998 before retiring.

The Red Sox wound up sending two prospects (neither of any value) to Toronto to reacquire Mike Stanley, who they had traded to the Yankees in 1997, and Stanley put up a .888 OPS for the rest of ’98, as the Sox cruised to the Wild Card.

Then, on July 31, it hit the fan. Forty-six players changed hands that day, while three more were promised as PTBNL. The Dodgers made a push for the Wild Card, acquiring Mark Grudzielanek and Carlos Perez fromt eh Expos for four prospects, including Peter Bergeron, Wilton Guerrero, and Ted Lilly. The Giants got Ellis Burks from the Rockies, and he’d finish the year with a .850 OPS. The Cardinals traded Royce Clayton and Todd Stottlemyre to Texas for Darren Oliver, Fernando Tatis, and a PTBNL. The Rangers also got Todd Zeile from the Marlins for two minor leaguers who never panned out. It was an upgrade on the magnitude of a couple wins, which helped the Rangers finish three up on the Angels.

But the highlight was undoubtedly the Mariners agreeing to trade Randy Johnson to the Astros for Carlos Guillen, Freddy Garcia, and John Halama. Johnson famously took Houston on his back and went 10-1over 11 starts with a 1.28 ERA. In context, he allowed one more run than he made starts. He pitched four shutouts, and struck out 116 in 84 innings. Halama and Garcia became rotation stalwarts in 1999 for the M’s, and Guillen would be the team’s starting shortstop within two years.

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