Most impactful trade deadline moves in MLB history
4:02 | MLB
Most impactful trade deadline moves in MLB history
Friday July 29th, 2016

Doyle Alexander did just about everything you could ask of a hired gun. Acquired by the Tigers from the Braves on Aug. 12, 1987, the gruff 36-year-old righty went 9–0 with a 1.53 ERA and three complete-game shutouts in 11 starts, helping Detroit overcome a 1 1/2-game deficit in the American League East race. As for the prospect the Tigers sent Atlanta, a former 22nd-round pick getting lit up for a 5.68 ERA in Double A: He didn't seem like anybody who would be missed, even given that he was just 20 years old.

Unfortunately for the Tigers, Alexander fizzled out in the 1987 ALCS against the Twins and then pitched poorly in the next two seasons—the last of his career—and that 20-year-old righty turned out to be John Smoltz, a future Cy Young winner, eight-time All-Star, staple of five pennant winners in Atlanta and ultimately a Hall of Famer. The Alexander-Smoltz trade wasn't exactly a deadline deal, as it occurred during the August waiver period, but it fits the pattern of the contender-sends-prospect(s)-in-exchange-for-veteran(s) trades that are so common in midseason. Sometimes, those trades provide the missing pieces for a playoff-bound team; sometimes, they come back to haunt the team sending the prospect away; sometimes, they do both.

What follows here is a chronological look at six other midseason deals—mainly around the July 31 deadline, but with a bit of latitude for interpretation—where the cost turned out to be far more than the contending team bargained for.

July 21, 1988: Yankees trade Jay Buhner plus two to Mariners for Ken Phelps

The Yankees were just two games out of first place in the AL East when they dealt for Phelps, a 33-year-old lefty-swinging slugger who had hit .260/.414/.539 with 65 homers for the Mariners over the previous 2 1/2 seasons. Along with pitching prospect Rick Balabon (a 1985 first-round pick) and a player to be named later (Troy Evers, New York's '85 second-rounder and also a pitcher), the Yankees included Buhner, a 23-year-old outfielder who had hit .198/.253/.319 for the Yankees in 99 plate appearances in '87 and '88.

Phelps hit .224/.339/.551 with 10 homers in 127 plate appearances for the Yankees the rest of the way, but they sank like a stone in the standings, and just over a year later, he was flipped to Oakland. Buhner, meanwhile, hit 10 homers for the Mariners during the remainder of the 1988 season, and after battling injuries for a couple of seasons, he emerged as a full-blown middle-of the lineup threat and the best friend of Ken Griffey Jr. From 1991 to '97, he clubbed 224 homers, becoming the 10th player in history to hit at least 40 in three straight seasons at the end of that run. This one was such a clunker that less than a decade later, it was referenced in Seinfeld, the most popular sitcom in the country.

Aug. 30, 1990: Red Sox trade Jeff Bagwell to Astros for Larry Andersen

The Red Sox had spent much of the season in a dogfight with the Blue Jays for the AL East lead, and by the end of August, they were pulling away despite a bullpen that aside from closer Jeff Reardon was largely dreadful; the unit's ERA was above 4.00 in every month and at 6.33 in July. General manager Lou Gorman needed another arm, and while he refused to part with Triple A prospects Mo Vaughn, Phil Plantier and Scott Cooper, he agreed to send Bagwell, then a Double A third baseman who had hit .333/.422/.457 with four homers—twice as many as the year before—in 136 games.

Andersen pitched brilliantly down the stretch, posting a 1.23 ERA in 22 innings en route to 1.2 WAR and helping the Sox win the AL East flag, but contrary to what Boston believed upon dealing for him, he left via free agency instead of re-signing. Bagwell shifted to first base the following spring and won NL Rookie of the Year honors, the start of a stellar 15-year run that helped the Astros to six postseason appearances, included an MVP award, and now has him on the doorstep of Cooperstown; he received 71.6% of the vote this past January.

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July 31, 1997: Mariners trade Jason Varitek and Derek Lowe to Red Sox for Heathcliff Slocumb

With a prime-aged Griffey, a peaking Buhner, a sage Edgar Martinez, a 21-year-old Alex Rodriguez and more, the 1997 Mariners had enough power to light up the entire west coast, setting a single-season record with 264 home runs, and they won the AL West for the second time in three years. What they did not have was any semblance of a reliable bullpen: Their relievers were crushed for ERAs of 6.37, 7.29, 4.35 and 6.48 through the first four months of the season, and it seemed just about everything that manger Lou Piniella did resulted in pouring more gasoline on the fire.

For some reason, Mariners GM Woody Woodward believed that Slocumb—who had saved 61 games with a 2.97 ERA for the Phillies and Red Sox over the previous two seasons but had a 5.79 ERA with 34 walks and 36 strikeouts in 1997—was not only the solution, but also worth giving up two players, including Seattle's 1994 first-round pick in the form of Varitek. Slocumb did improve to a 4.13 ERA down the stretch, but he lost his job and was dealt again the following year. Varitek helped the Red Sox to a playoff berth the following year, the first of seven the Sox would make during a 15-year career in Boston that included three All-Star appearances.

As for Lowe, a 24-year-old rookie scuffling along with a 6.96 ERA for the Mariners: He had a more up-and-down run in Boston. He did, however, lead the AL in saves in 1998 and win 21 games and throw a no-hitter in 2002, finishing third in that year's AL Cy Young voting. The high point for his Boston tenure was 2004, when despite a 5.42 regular-season ERA, he became the first player ever to win three clinching games in a single postseason, capped by the one that broke the Red Sox' 86-year championship drought.

June 27, 2002: Expos trade Cliff Lee, Brandon Phillips and Grady Sizemore to Indians for Bartolo Colon

In an attempt to seize the upper hand in negotiations for the next Collective Bargaining Agreement during the 2001–02 off-season, commissioner Bud Selig and the owners named the financially struggling Expos one of four teams that could potentially be contracted. Early the next year, the league facilitated an unholy trio of franchise transactions that allowed Expos owner Jeffrey Loria to buy the Marlins, whose owner John Henry in turn bought the Red Sox, with the Expos becoming wards of the other 29 teams.

Led by Vlad Guerrero, the Expos were a reasonably talented team, but when they were 6 1/2 back in the NL East and five back in the wild-card race, acting GM Omar Minaya thought that acquiring a frontline pitcher would be just what they needed to make a run at a postseason spot. He pulled the trigger on a five-player deal with the Indians that brought in Colon, who had gone 10–4 with a 2.55 ERA with the Indians. The 29-year-old fireballer pitched well for the Expos (10–4, 3.31 ERA), but they soon slipped below .500 and never got back into the race.

The haul the Expos surrendered was massive, and it helped doom baseball in Montreal. Sizemore debuted in 2004 and went on to make three All-Star appearances and average 27 homers and 29 steals from '05 to '08. Lee would finish fourth in the AL Cy Young balloting in 2004 and win it in '08 after being knocked back to the minors in the previous season. Phillips struggled so badly in regular duty in 2003 that he was sent back to the minors for most of two seasons; he didn't emerge as a star until being dealt to the Reds in '06. The fourth player the Indians received, first baseman Lee Stevens, was a bust. Still, it was one of the many crimes done to the Expos during their last leg in Montreal.

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July 31, 2007: Braves trade Elvis Andrus, Neftali Feliz, Matt Harrison and Jarrod Saltalamacchia plus one to Rangers for Mark Teixeira and Ron Mahay

After missing the playoffs in 2006—the end of a remarkable run dating back to 1991 and interrupted only by the ’94 players’ strike—the Braves were in the thick of both the NL East and wild-card races when they acquired the 27-year-old Teixera from the Rangers to replace struggling Scott Thorman at first base. He hit a sizzling .317/.404/.615 with 17 homers in 240 plate appearances for them, and the 36-year-old Mahay pitched to a 2.25 ERA, but the deal turned out to be a heist and a half for the Rangers.

Saltalamacchia was merely an adequate part-time catcher, and high A lefty Beau Jones, who was also in the deal, never panned out. But Andrus, Feliz and Harrison played key roles on the Rangers' 2010 and '11 AL champions as their starting shortstop, closer and starting pitcher, respectively. Feliz was an All-Star and AL Rookie of the Year in 2010; Andrus earned All-Star honors in '10 and '12; and Harrison made the All-Star team in the latter year, as well for a team that lost the wild-card game.

July 8, 2008: Cubs trade Josh Donaldson plus three to Athletics for Rich Harden and Chad Gaudin

The Cubs were 54–36 with the NL's best record and en route to their second straight division title when GM Jim Hendry attempted to upgrade both ends of the pitching staff by acquiring Harden, a brilliant but oft-injured 26-year-old righty, and Gaudin, a mediocre swingman in the midst of a good season. To get the pair, the Cubs gave up fringe outfielder Matt Murton, utilityman Eric Patterson, 22 year-old starter Sean Gallagher and Donaldson, a 2007 supplemental first-round pick who was then 22 and scuffling in Class A.

Harden pitched brilliantly, posting a 1.77 ERA in 12 starts and helping the Cubs win the Central, though Gaudin pitched poorly. Murton, Patterson and Gallagher never amounted to much in Oakland. But while it would take 3 1/2 more seasons and a position change to third base, Donaldson emerged as a useful regular in 2012 and then produced a pair of MVP-caliber seasons totaling 15.0 WAR in '13–14, helping the A's to back-to-back postseason appearances. This was one of Billy Beane's greatest thefts; if only he had fared as well upon unloading Donaldson.

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