1) July 5, 1987: San Francisco Giants trade Chris Brown, Keith Comstock, Mark Grant and Mark Davis to the San Diego Padres for Dave Dravecky, Kevin Mitchell and Craig Lefferts
What I knew about Chris Brown was that he was young and could hit. "There's no question in my mind that Chris Brown is the best third baseman in the National League," his GM said a year before this trade. But what my dad told me about Chris Brown the day this trade was made was that his nickname was Chris "I'm Hurt, I'm Hurt" Brown. It was my very first exposure to snark in baseball. His teammates joked that the pitching staff had more complete games than Brown, and Joel Youngblood told a reporter, simply, "He makes me sick." I could probably mount a spirited defense of him in hindsight, pointing out that the undiagnosable shoulder injury he complained of was ultimately diagnosed as a detached tendon, and he later underwent a complicated surgery. But Brown didn't do his reputation any favors. He pulled himself from the Padres' lineup just after this trade with a sore wrist (x-rays revealed no fracture) after he was hit by a pitch in batting practice (for the fourth time!). "He's not playing until he says he's ready," said his new manager. "That's all I can go by." He would later miss time with a bruised tooth. After he joined the Tigers, he sat out after he slept on his eye wrong. Just 25 when the trade was made, he hit eight more home runs in his career.
Meanwhile, Dravecky, Mitchell, and Lefferts combined for 5.9 WARP over the rest of the 1987 season, and the Giants made the playoffs for the first time since 1971; the Padres' four combined for 0.9 WARP that half-season. Dravecky's comeback start in 1989 is the most memorable moment for a generation of pre-Spiezio Giants fans, and Mitchell's MVP season of 1989 burned two numbers into my mind for good: 47 (home runs) and 125 (RBIs). I vaguely recall that one of the Marks that the Giants gave up would win the Cy Young award a couple years later. I quite clearly recall not caring. —Sam Miller
2) July 13, 1987: Chicago Cubs trade Steve Trout to the New York Yankees for Rich Scheid, Bob Tewksbury, and Dean Wilkins
“Lou, I just won you the pennant: I got you Steve Trout.” The Gods hate hubris, and both Steinbrenner and his manager Lou Piniella were rapidly punished for those words. Always a pitcher short, the Yankees of the mid-1980s were ever on the hunt for the veteran starter that would take them over the top. Trout, a soft-tossing, pitch-to-contact lefty was an unlikely choice for a hero: the 29-year-old had a career ERA was 3.95 in about 750 career innings, a league average figure, his strikeout-walk ratio tended to break even at best, and he had never pitched 200 innings in a season. Still, he had a 3.00 ERA through 11 starts at that point and the Yankees’ rotation was a patchwork nightmare that included Dennis Rasmussen and Charlie Hudson, both of whom would be sent to the minors at different points that season in fits of lordly pique by Steinbrenner; Rick Rhoden; and the ancient trio of 36-year-old Ron Guidry, 42-year-old Joe Niekro, and 44-year-old Tommy John.
Trout proved to be perhaps the most disastrous midseason pickup ever. His first start was a 20-3 loss to the Texas Rangers and but for a fluky six shutout innings against the Royals his third time in pinstripes he was mercilessly battered. Soon dropped from the rotation, he would spend the remainder of the year alternating between starting and relief assignments. Overall, he went 0-4 with a 6.60 ERA in 14 games. The Yankees were leading the division by three games when Trout was acquired; they finished nine games out. As for the three pitchers the Yankees gave up, the only one to develop was Tewksbury. It took three years, but he would eventually become one of the best control pitchers of all time. In trading him, the Yankees said that “everything had to be right” for Tewksbury to win. Yes, it’s often like that with rookie pitchers. Patience!—Steven Goldman
3) August 12, 1987: Detroit Tigers acquire Doyle Alexander from the Atlanta Braves in exchange for John Smoltz
Few late-season acquisitions have performed as admirably as veteran starter Doyle Alexander, whose 9-0 record and 1.53 ERA down the stretch for the 1987 Tigers helped Detroit run down Toronto and win the AL East. To this day, however, there are those who cite this as a terrible trade for Detroit given what turned out to be the high cost they paid to acquire the 37-year-old sinkerballer: John Smoltz, future lynchpin of Atlanta’s 1990s dynasty.
To me, however, that opinion doesn’t just miss the forest for the trees; it denies that forests exist at all. Flags fly forever, and Detroit clearly would not have gotten its playoff ticket punched without Alexander’s tremendous work. Losing to the “Dome of Destiny” Twins in that year’s ALCS doesn’t invalidate the decision to go all-in with a squad featuring Trammell, Whitaker, Gibson, and Morris nearing the ends of their peaks and getting production from a 40-year-old Darrell Evans. Moreover, Smoltz was a 20-year-old former 22nd round pick who was in the midst of logging 86 strikeouts and 81 walks in 130 Double-A innings. That’s exactly who you should trade for a veteran starter at the deadline. The fact that Smoltz turned into a winning lottery ticket doesn’t mean the Tigers were wrong for selling him to the Braves at 20 times his face value any more than winning a Keno jackpot proves it’s smart to play Keno at all. —Ken Funck
4) September 21, 1987: Chicago Cubs trade Dickie Noles to Detroit Tigers for a Player to Be Named Later (Dickie Noles)
A veteran swingman, Noles was famous for two things prior to 1987: being the 1980 World Series hero for the Phillies, and being arrested in a bar room brawl in Cincinnati in 1983. A recovering alcoholic who is now among the most respected sports substance abuse counselors in the country, Noles was a non-roster invitee to the Cubs in 1987, made the team, and pitched well enough that the Tigers, looking to bolster their bullpen for the last two weeks of the year, acquired him for a player to be named later. Noles saved two games for Detroit, including a key extra inning game against front-running Toronto.
The Tigers made the playoffs, lost in the ALCS to the Twins, and at the end of October, faster than you can say “Harry Chiti,” Noles was shipped back to the Cubs. Not surprisingly, a team (believed to be Toronto) filed a grievance with the Commissioner. Tigers general manager Bill Lajoie made it clear that the deal was originally the precursor to a bigger, three-way trade that would have sent former AL MVP Willie Hernandez to the Cubs, along with Phillies third baseman Rick Schu, while the Tigers would have received another player and Phillies were to get former All-Star first baseman Leon Durham from Chicago. The reason the deal didn’t go as planned: Phillies President Bill Giles, gave up his GM duties and hired Woody Woodward who had no interest in Durham. Cubs GM Dallas Green resigned just days after Noles was returned (although that had more to do with a power struggle with Tribune Management). Noles made just three more appearances in the big leagues after 1987. It would be another 18 years before a player was traded for himself, when John McDonald was traded from, ironically, the Jays to the Tigers and back.—Mike Ferrin
5) July 21, 1988: New York Yankees trade Jay Buhner, Rich Balabon, and Troy Evers to the Seattle Mariners for Ken Phelps
Two games back in the AL East on July 21, 1988, the Yankees made a move that would earn George Steinbrenner the ire of Frank Costanza and many other Yankees fans for a decade. In return for a hitter with power and not much else, Ken Phelps, the Yankees sent Jay Buhner, Rich Balabon, and a player later to be named (Troy Evers) to the Seattle Mariners. Phelps went on to have a pretty successful remainder of the season for New York, but the team was unable to take advantage and finished in fifth place (although only 3.5 games back in a very tight division). Phelps’ performance, however, dropped substantially in 1989, as did the Yankees, leading to Phelps being traded to the A's for a minor-leaguer named Scott Holcomb. Buhner, on the other hand, went on to a 20+ WARP career with the Mariners, showing good power, a great arm, and becoming a fan favorite. To add insult to injury, Buhner inflicted more damage on the Yankees than on any other team, including a .458/.500/.625 line against them in the 1995 Divisional Series. —Dan Turkenkopf
6) June 21, 1989: Oakland Athletics acquire Rickey Henderson from the New York Yankees in exchange for Greg Cadaret, Eric Plunk, and Luis Polonia
Oakland without the Raiders? Oakland without Rickey? Yeah, things got weird in the 1980s. But in June 1989, the A's viewed Henderson as the final piece of the puzzle and traded Eric Plunk, Greg Cadaret, and Luis Polonia to the Yankees to bring back their homegrown star. Henderson's second act produced MVP honors in the ALCS in '89, a World Series championship later that fall, and the best season of his Hall of Fame career in '90. He was fantastic for the A's until he was dealt to the Blue Jays in '93. Two years later, the Raiders moved back from Los Angeles, though that homecoming hasn't gone nearly as well as Rickey's. —Marc Carig
7) August 8, 1990: Montreal Expos acquire Moises Alou, Scott Ruskin, and Willie Greene from the Pittsburgh Pirates in exchange for Zane Smith
Moises Alou had a fine, albeit injury-plagued, 17-year career in the major leagues that ended in 2008. He had a .303/.369/.515 slash line with 332 home runs while appearing in six All-Star Games and winning two Silver Sluggers. The former outfielder is not Hall of Fame material, but he certainly belongs in the Hall of Pretty Darn Good. What always sticks out in my memories of Alou, however, is that he is the only player I know who was the player to be named sooner in a trade. On the night of August 8, 1990, the Pirates traded for Expos left-hander Zane Smith, giving up left-handed reliever Scott Ruskin, top shortstop prospect Willie Greene, and a player to be named later. The first thing Pirates general manager Larry Doughty said when he addressed the media, however, was, "it's always difficult to give up a player of Moises Alou's caliber." Talk about letting the cat out of the bag!
The reason for keeping Alou's name a secret had nothing to with the fact that the Pirates were in a tight National League East race with the Mets. Instead, the Pirates' Class AAA Buffalo farm club was locked in a battle for the East Division title in the American Association, and Alou was one of the Bisons' top players. Buffalo was the premier minor-league franchise at the time, drawing one million fans a year to Pilot Field as the city angled for a major-league expansion franchise. The Pirates desperately wanted to keep the Bisons' ownership happy in order to retain the affiliation. Eight days after the trade, Major League Baseball ordered the Pirates to send Alou to the Expos. While the Pirates won their division—in large part because Smith went 6-2 with a 1.30 ERA in 11 games—Buffalo came up short in its race, sans Alou, as it finished one game behind the Reds' Nashville affiliate. —John Perrotto
8) July 31 1997: Seattle Mariners trade Jason Varitek and Derek Lowe to Boston Red Sox for Heathcliff Slucumb
Back in 1997, the Red Sox were muddling through the first season of Jimy Williams's tenure as Red Sox manager, eventually finishing six games under .500. General Manager Dan Duquette was looking for any way possible to improve the club for 1998, and moving Slocumb was a good fit. Slocumb was a 31-year-old closer who blew five games in 22 chances by the time he was traded in July. Seattle needed a closer to stabilize their bullpen situation—even one who had his own difficulties closing games. Duquette couldn't deal with the uncertainty at the end of games any longer and sent Slocumb to Seattle for Derek Lowe and Jason Varitek.
In the deal, the Red Sox ended up acquiring two key members of their run to the 2004 championship. Varitek became a mainstay behind the plate, supplanting Scott Hatteberg as the everyday catcher, and cemented his reputation for working with pitching staffs and calling games. Meanwhile, Derek Lowe was used in multiple roles during his time in Boston, saving 42 games in 2000 and winning 21 games in 2002. Both were key contributors to the 2004 championship season with Lowe winning each series-clinching game. Not bad considering Slocumb was out of Seattle by 1998 and out of baseball in 2000. —Corey Dawkins
9) July 31, 1998: Houston Astros acquire Randy Johnson from the Seattle Mariners in exchange for Freddy Garcia, Carlos Guillen, and John Halama
The first thing that comes to mind when I think of this trade is the excitement I had at the prospect of seeing Randy Johnson bat on a regular basis. I know, I know—there was already interleague play by that time. Still, I was thrilled at the prospect. The second thing that comes to mind when I think of this trade is just how dominant the Big Unit was for his two months in Houston, helping lead a ridiculously talented Astros team to 102 wins. In 11 starts in the National League, Johnson threw 84 innings while striking out 116 batters and walking 26. He also gave up a total of 12 runs to his new NL brethren. With all apologies to Rick Sutcliffe and C.C. Sabathia, no midseason acquisition had a more dominant introduction to his new league than Randy Johnson. —Larry Granillo
10) July 31 2003: New York Yankees acquire Aaron Boone from the Cincinnati Reds in exchange for Brandon Claussen, Charlie Manning, and cash
With what I fancied an enlightened appreciation for the unsung value of prospects, I lamented this move when it was made. Claussen had been ranked by Baseball America as the Yankees’ top pitching prospect (and third-best prospect overall) entering the 2003 season, and he’d posted a 2.75 ERA in Triple-A prior to the trade. The Yankees’ rotation at the time featured two quadragenarians and—even worse—Jeff Weaver, so it seemed a shame to sacrifice a viable in-house candidate to fill a forthcoming vacancy. Little did I know that Yankees pitching prospects had a history of being overhyped—Ed Yarnall, anyone?—and that the Yankees had (and continue to have) little use for arms that hadn’t already succeeded elsewhere.
Lost in the aftermath of Boone’s historic homer was his performance before that fateful at-bat against Tim Wakefield, which was unremarkable at best. Boone’s TAv in pinstripes down the stretch was a near-match for his league-average career mark and only a slight improvement over Robin Ventura’s .255 pre-break showing with the bat. Prior to his homer, Boone had flailed his way to a 5-for-31 playoff performance (good for a slash line of .161/.212/.194), looking more like a potential goat than a player who was about to make an epithet his middle name in New England with a single swing.
If we evaluate the trade on a WARP-for-WARP basis, the Reds come out ahead: Manning never made it to the majors with Cincinnati, but Claussen amassed 3.5 WARP for them over approximately 310 innings from 2004-2006, dwarfing Boone’s total in New York. Of course, the Boone trade serves as a reminder that there’s much more to trade evaluation than determining which team won the WARP war. According to Sean Smith, the Yankees’ win probability added as a result of Boone’s ALCS-winning blow was worth roughly .18 pennants and .09 World Series—and if there’s one thing that every team’s supporters know instinctively, it’s that .18 pennants fly forever. —Ben Lindbergh
11) July 30, 2004: New York Mets trade Scott Kazmir and Jose Diaz to the Tampa Bay Devil Rays for Victor Zambrano and Bartolome Fortunato
This one was, and remains, all about timing. At the time, the deal looked like a howler for Jim Duquette and the Mets. Scott Kazmir was the team's top prospect—one that ownership had labeled untouchable before the 2004 season. Zambrano was an unbridled flamethrower who had posted three straight seasons with walk rates above five per nine and ERAs above four. Kazmir had six years of team control left; Zambrano had three. The Mets stood in fourth place and were seven games behind in the NL East on the day of the trade—a day on which they also acquired Kris Benson from the Pirates—a fact that made Duquette's statement to Lee Jenkins that they "still [had] a chance, [were] still in the hunt and [were] still in the mix" quite unbelievable. The Times noted coolly, "Concerns about Zambrano are over his health and his control."
Fast forward to 2011, and exactly the same concerns apply to Scott Kazmir, who remains a free agent after he was released by the Angels earlier this year. Make no mistake; Kazmir was the better bet. He accumulated 17 WARP for Tampa Bay over five seasons. Zambrano compiled just over 2 WARP for the Mets over parts of three seasons. But this wasn't dealing away Randy Johnson or John Smoltz or even Tom Seaver. This was missing the top of the market by a few years. Branch Rickey liked to trade players a year too early rather than a year too late; maybe Jim Duquette just traded Scott Kazmir four years too early. Unlike the cataclysm the trade seemed to portend at the time, the trade now stands for the proposition that pitchers are risky and timing is everything. —Tommy Bennett
12) July 31, 2005: Chicago White Sox acquire Geoff Blum from the San Diego Padres in exchange for Ryan Meaux
The best part about this trade is that Blum was never a very good player outside of a strange 2002 season. Entering the deadline, Blum was hitting .241/.321/.375 with San Diego and had hit .255/.311/.390 in the three seasons prior. He gave the White Sox some insurance at third base and a switch-hitter off the bench, but not much else. Over the rest of the regular season, Blum hit .200/.232/.274 but found himself on the playoff roster. Blum appeared in one playoff game prior to the World Series—gaining an at-bat in a blowout against the Red Sox—but walked to the plate for the second and final time of that postseason in Game Three.
The score was tied at five and it was the top of the 14th inning. Ezequial Astacio—the second most popular Astacio to pitch for Houston during that decade—was on the hill and delivered a 2-0 pitch to Blum. Because this is baseball, and in baseball the most frivolous of transactions can sometimes transcend their nondescript nature in moments of brilliance, Blum homered. It was an expected event, given that you knew nothing of Geoff Blum to begin with. Meaux, by the way, was out of the Padres system by 2007 and out of the league by 2008. —R.J. Anderson
13) July 31, 2007: Pittsburgh Pirates acquire Matt Morris from the San Francisco Giants in exchange for Rajai Davis
Sixth-place teams are not usually buyers at the end of July. But, to borrow Joaquin Andujar’s favorite English word, youneverknow. For reasons as obscure then as now, general manager Dave Littlefield and the 2007 Pirates found themselves in the market for starting pitching despite being 13.5 games out on July 31 and barreling toward 94 losses. And, more baffling still, apparently price was no object.
Meanwhile, San Francisco—en route to 91 losses and a fifth-place finish—had taken on the more conventional role for a team facing a double-digit deficit in the standings with two months to play. The Giants and GM Brian Sabean were looking to sell, shed payroll, or both. In Littlefield, he found the ideal match, shipping 32-year-old Matt Morris and the roughly $15 million left on his contract to Pittsburgh for 26-year-old outfielder Rajai Davis and a minor leaguer.
Morris never quite provided the rotation with the veteran presence the Pirates sought. He threw 84 1/3 mediocre innings in 16 starts before Pittsburgh released him a month into the 2008 season. Fans hoping the trade was a sign that new principal owner Robert Nutting would raise payroll significantly were ultimately disappointed as well. Littlefield was fired five short weeks later. So, if nothing else, the Morris trade helped kick-start Pittsburgh’s rebuilding process.—Jeff Euston
14) July 31, 2007: Atlanta Braves acquire Mark Teixeira and Ron Mahay from the Texas Rangers in exchange for Neftali Feliz, Matt Harrison, Jarrod Saltalamacchia, Beau Jones, and Elvis Andrus
On the final day of July in 2007, Texas Rangers general manager Jon Daniels drove an unmarked white van up to the gates of the Atlanta Braves farm system, opened the sliding door, scooped up a bounty of quality prospects, and the rest of the story is rather graphic. Here’s a brief (and G-rated) summary of the subsequent crime: Mark Teixeira was an excellent addition to the roster, but he couldn’t carry the Braves to post-season glory in 2007 and was sent to the Angels the following summer for Casey Kotchman and Steve Marek. The Rangers developed Andrus into an All-Star shortstop, Feliz into a Rookie-of-the-Year-winning All-Star closer, and Harrison into a quality middle-of-the-rotation starter. Additionally, after failing to develop Salty into a first-division catcher, they flipped him to Boston for minor league fire-baller Roman Mendez. This was a Herschel Walker trade for the Rangers, giving them a much needed shot of talent in the minor league arm and aiding in their eventual ascent to October baseball. For Atlanta, it didn’t push them over the top, but it didn’t exactly push them over the edge either; instead, the Braves get to look back fondly at what could have been without suffering permanent paralysis from the trade itself. The ability to survive is a testament to the Braves’ talent evaluators and developmental staff as they’ve been able to keep the system stocked with impact prospects since that fateful day in 2007. A lesser organization would still be feeling the effects of such a one-sided malfeasance. —Jason Parks
15) July 7, 2008: Milwaukee Brewers acquire C.C. Sabathia from the Cleveland Indians in exchange for Matt LaPorta, Michael Brantley, Rob Bryson, and Zach Jackson
Before the trade, the Brewers were half a game behind the Cardinals in the Wild Card race. The team climbed on Sabathia’s back, and he carried them into the playoffs by one game over the Mets. The Brewers won 14 of the 17 games he started in the regular season, seven of which were complete games. The Brewers received 4.2 WARP from Sabathia along with the playoff berth, while the Indians have received a cumulative one WARP from their haul of prospects so far. LaPorta and Brantley are still young enough to turn into productive major league players, but neither has shown much yet. The Brewers also received two compensation picks after Sabathia left in free agency, with which they selected Kentrail Davis and Max Walla, though neither player has yet sniffed Double-A. Unless one of the prospects received by the Indians has a breakout year, it looks like the Brewers won this trade rather handily despite only getting three months of production. —Chris St. John
16) July 8, 2008: Oakland Athletics trade Rich Harden with Chad Gaudin to the Chicago Cubs for Josh Donaldson, Sean Gallagher, Matt Murton, and Eric Patterson
Being a Cubs fan is the continued triumph of hope over experience. The experience in this case was primarily Mark Prior and Kerry Wood, oft-injured power pitchers that were electric when they were able to take the mound at all. The hope was that a team that had made the playoffs the previous year, could avoid being bounced out of the playoffs after three straight losses by bolstering its rotation. Harden was supposed to supply the answer.
To get him, the Cubs gave up prized pitching prospect Sean Gallagher as well as two players (Matt Murton and Eric Patterson) who seemed like they were never going to get a chance to play in Chicago anyway and a respectable catching prospect named Josh Donaldson. He hasn't panned out yet; neither has Gallagher, who the A's later traded away for Scott Hairston as a player to be named later. Murton ended up setting the single-season hit record in Japan, but before that bounced around the majors, and Patterson has turned into a journeyman as well. Meanwhile, Harden actually stayed healthy and was incredible down the stretch. He made it look so easy to rack up double-digit strikeouts game after game after game. So the deal was a success, right? Well, sure—right until the first round of the playoffs, where the Cubs were once again bounced from the first round without winning a single game. Like I said, it's the triumph of hope over experience.—Colin Wyers
17) July 31, 2008: Los Angeles Dodgers acquire Manny Ramirez from the Boston Red Sox in a three-team trade with the Pittsburgh Pirates.
Once upon a time, when he was a Cleveland Indian, Manny Ramirez was a favorite of mine, but years rooting against him wearing a Red Sox uniform had hardened me to his considerable gifts. Particularly given what they gave up—Andy La Roche and Bryan Morris—and what they needed—a middle-of-the-lineup threat who could force the execrable Juan Pierre out of the lineup—it didn't take much to re-embrace Manny. All he did was hit an ungodly .396/.489/.743 with 17 home runs in 53 games, proving Ball Four author Jim Bouton's point: if you slug .743, you can have hair down to your ass. Ramirez hit .520/.667/1.080 in the postseason, helping the Dodgers to their first playoff series win in 20 years. Whatever the controversies that followed, those three months were absolutely worth it, as fun as anything has been for a Dodger fan in two decades. —Jay Jaffe