10 worst deadline deals in MLB history

Mark McGwire
The A's traded Mark McGwire, who went on to greatness in St. Louis.
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Dayn Perry

Dayn Perry is a frequent contributor to His second book, "Reggie Jackson: The Life and Thunderous Career of Baseball's Mr. October," is available from HarperCollins Publishers. Read more of his work at the NotGraphs blog.


As the July 31 non-waiver trade deadline looms, it's worth remembering that these things we call deadline deals can be risky endeavors.

Indeed, history is littered with trades that may have looked sensible at the time but turned out to be deeply damaging to one of the teams involved. So what are the worst of such deals?

To explore this question, we'll keep the focus on the contemporary era — when the "deadline deal" truly became a phenomenon unto itself. That means the pool of eligible trades will span from 1985 unto the present day, the last 25 years or so. As well, we'll consider only those trades that went down during what can reasonably be considered the non-waiver period (from June 15 through July 31). As such, we'll necessarily exclude a couple of August trades that otherwise qualify as foul-smelling disasters (e.g., the trade that sent Jeff Bagwell out of Boston).

With those criteria laid out, let's count down the 10 worst deadline deals of the modern age…

10. July 31, 1998 — The Astros trade Freddy Garcia, Carlos Guillen and John Halama to the Mariners for Randy Johnson.

To be sure, Johnson was outstanding during his brief time as an Astro. After the trade, he posted a sparkling 1.28 ERA and whiffed 116 batters in 84.1 innings. The Astros went 37-16 after picking up Johnson, but they lost to the Padres in the NLDS in four games. Johnson pitched very well in two playoff starts, but because of a lack of run support he lost both games. For their troubles, the Mariners picked up three players who would fill vital roles in the seasons to come. Garcia gave the M's a half-decade of effective pitching, Halama pretty much did the same, and Guillen established himself as one of the most underrated players in the game.

9. July 21, 1988 — The Yankees trade Jay Buhner to the Mariners for Ken Phelps.

With good cause, this swap stuck in the craw of Frank Costanza. Indeed, Buhner went on to hit 307 of his 310 career home runs as a Mariner. His stay in Seattle also included three straight 40-homer seasons, one All-Star appearance and one Gold Glove. Meantime, Phelps hit for power down the stretch in '88, but he was soon on the log flume out of baseball.

8. July 29, 1988 — The Red Sox trade Curt Schilling and Brady Anderson to the Orioles for Mike Boddicker.

Boddicker was effective in two seasons in Boston, especially so in 1990 (228.0 innings, 123 ERA+), but consider the cost. Schilling, who was a 21-year-old minor leaguer at the time, went to a likely Hall-of-Fame career (part of which would of course unfold in Boston years later). And Anderson also put together a nifty decade or so as an All-Star center fielder. Considering that Boston was unable to dig up a reliable center fielder between Ellis Burks and Johnny Damon — a gap that roughly coincides with Anderson's prime — it's even more of a loss. Interestingly, Schilling was also a part of another deadline stinker: the 2000 deal in which the Phillies sent him to Arizona in exchange for Omar Daal, Vicente Padilla, Travis Lee, and Nelson Figueroa.

7. July 28, 1995 — The Blue Jays trade David Cone to the Yankees for Marty Janzen, Jason Jarvis and Mike Gordon.


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As a Yankee, Cone tossed a memorable perfect game and was a key part of the team's dynastic run in the late 1990s (he was also the co-ace of the legendary '98 squad). As for the Jays, only one of the players they received even made the majors. That was Janzen, and in two partial seasons in Toronto he compiled an ERA of 6.39.

6. July 23, 2003 — The Pirates trade Aramis Ramirez, Kenny Lofton and cash to the Cubs for Bobby Hill, Jose Hernandez and Matt Bruback.

Ramirez has become, without exaggeration, the greatest Cub third baseman since Ron Santo (203 bombs and counting as a Cub, plus two All-Star appearances and two top-10 MVP finishes), and Lofton batted .327 down the stretch in '03 as the Cubs almost won the pennant. In Pittsburgh, meanwhile, Hernandez didn't hit in his half-season of work, Hill never realized his potential, and Bruback never made the majors. That's to say nothing of the fact that the Pirates threw in cash — something they tend not to have much of.

5. July 31, 2007 — The Braves trade Elvis Andrus, Neftali Feliz, Jarrod Saltalamacchia, Matt Harrison, and Beau Jones to the Rangers for Mark Teixeira and Ron Mahay.

Depending on how things pan out in Arlington in the coming seasons, this one could be even higher on the list. When the Braves pulled off this deal, they were just 3.5 games out of first place, but they were only game over .500 the rest of the way. Teixeira raked as a Brave, but they missed the post-season and traded him away at the 2008 deadline for next to nothing. As for the Rangers' side of things, they landed one of the best young shortstops in baseball (Andrus) and one of the best young arms in baseball (Feliz). As well, Saltalamacchia may yet be useful (he's still just 25), Harrison is contributing at the highest level in 2010, and even James looks like he'll have a career as a second lefty out of the pen. The Braves will regret this deal for years to come.

4. July 31, 1997 — The A's trade Mark McGwire to the Cardinals for Eric Ludwick, T.J. Mathews and Blake Stein.

This one requires little explanation. The A's received three players who achieved little in the majors, and Mark McGwire went on to hit 220 homers as a Cardinal, seize the single-season home run record for a time, and help them to a pair of division titles. McGwire, despite playing the healthy majority of his career in Oakland, is now one of the defining players of the late 90s and squarely identified as a Cardinal.

3. July 18, 1993 — The Padres trade Fred McGriff to the Braves for Melvin Nieves, Donnie Elliot and Vince Moore.

In the minds of many, this trade stands as the deadline deal of the modern era. That's a justifiable stance. After the trade, McGriff hit .310 AVG/.392 OBP/.610 SLG for the Braves. He was just as effective the following season, and then in the Braves run through the '95 post-season he was simply devastating. As for the return package, no one achieved anything of consequence on San Diego's watch.

2. July 31, 1997 — The Mariners trade Derek Lowe and Jason Varitek to the Red Sox for Heathcliff Slocumb.

At the time of this ill-fated trade, Slocumb had a 5.79 ERA. This bears repeating: Seattle paid dearly for a reliever with an ERA in sniffing distance of 6.00. In doing so, the M's parted with two players — Varitek and Lowe — who would greatly help the Red Sox become the top organization of the "aughts." Lowe would save 40-plus in one season for Boston and then win 20-plus two years later. Varitek would become captain and key two World Series winners.

1. June 27, 2002 — The Expos trade Cliff Lee, Brandon Phillips, Grady Sizemore, and Lee Stevens to the Indians for Bartolo Colon and Tim Drew. 

Cliff Lee? A Cy Young on the mantle and a deserved reputation as one of the best lefties in the game. Brandon Phillips? A Gold Glove-caliber second baseman with pop. Grady Sizemore? A three-time All-Star who, although injured, is still just 27. For all that, the Expos received three months of Colon. Colon was effective in Montreal, but the Expos missed the postseason and that winter dealt him to the White Sox for much, much less than they paid for him. On the upside, if the Expos/Nationals had held onto Lee, Phillips and Sizemore, then they probably never would've been in position to draft Stephen Strasburg.

Tagged: Red Sox, White Sox, Indians, Tigers, Twins, Yankees, Rangers, Braves, Cubs, Reds, Derek Lowe, Jason Varitek, Cliff Lee, Mark Teixeira, Grady Sizemore, Matt Harrison

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