20. Tigers acquire past-prime Lynn
Fred Lynn was a very good player for a long time. He's no Hall of Famer, but if there actually were a such thing as the Hall of the Very Good, he'd be in there. He was not, however, very good in 1988 at the age of 36, when the Tigers dealt for him.
The deal was the Orioles shipping Lynn to the Tigers on Aug. 31 for players to be named later (Cesar Mejia and Robinson Garces) and Chris Hoiles.
Lynn hit .237/.315/.391 in his 144 games with the Tigers in two seasons. They failed to make the postseason with him on board.
Hoiles, by the way, was a nice get for the O's. He played for them for 10 years, hitting 151 homers with a 119 OPS+ and serving as a reliable catcher. The Orioles made the playoffs twice with him on board.Credit: Getty Images
19. Cubs get "one dog"
The Cubs and Mets got together for a pretty big trade on Aug. 8, 1997.
The Cubs got Lance Johnson, Mark Clark and Manny Alexander while the Mets got Brian McRae, Mel Rojas and Turk Wendell.
Johnson, Alexander and Clark had a hand in the Cubs winning the NL wild card spot in 1998 while the Mets would make the playoffs in 1999 and the World Series in 2000.Credit: Getty Images
18. Red Sox acquire Billy Wagner
Remember when Billy Wagner pitched for the Red Sox? We'll forgive you if not. It was only 15 games in 2009. He put up a 1.98 ERA in 13 2/3 innings with 22 strikeouts, helping the Red Sox to win the AL wild card.
Wagner was dealt on Aug. 25 that season for players to be named later (Chris Carter and Eddie Lora).Credit: Getty Images
17. Astros get Garner
On Aug. 31, 1981, the Astros would acquire a man who would become a franchise fixture in Phil Garner. They sent the Pirates Johnny Ray and players to be named later (Randy Niemann and Kevin Houston).
Garner would spend parts of seven seasons with the Astros, making the playoffs in 1981 and 1986. He would later manage the Astros for four seasons, twice making the playoffs and winning the 2005 pennant, the only one in franchise history to this point.Credit: Getty Images
16. Giants get Reuschel
On Aug. 21, 1987, the Pirates sent starting pitcher Rick Reuschel to the Giants for Scott Medvin and Jeff Robinson.
In parts of five seasons, Reuschel went 44-30 with a 3.29 ERA (104 ERA+) for the Giants. Of note, in 1989 Reuschel was the NL starter in the All-Star Game and helped lead the Giants to the NL pennant.Credit: Getty Images
15. Twins acquire Big Papi
The Twins releasing David Ortiz before he became a Red Sox legend has been notorious for years, but they weren't the only team to whiff on Big Papi.
On Aug. 29, 1996, the Mariners decided to trade for Dave Hollins for a player to be named later. That player would be Ortiz.
Hollins only played in 28 games for the Mariners and they missed the playoffs.Credit: Getty Images
14. Canseco heads to Texas
Jose Canseco was in the middle of his prime. He had won a Rookie of the Year and MVP. He was a five-time All-Star. The A's were in the midst of their fourth playoff run in five years.
And yet, the A's broke up the Bash Brothers and traded Canseco to the Rangers on Aug. 31, 1992 for Jeff Russell, Ruben Sierra, Bobby Witt and cash considerations.
In parts of three seasons, Canseco would hit .269/.363/.512 with 45 homers in Texas, but he didn't see the postseason again until he was on the Red Sox in 1995.
The A's lost to the Blue Jays in the ALCS, four games to two, that season and then didn't make the playoffs again until 2000.Credit: Getty Images
13. Expos get Alou
On Aug. 8, 1990, the Expos made a deal with the contending Pirates that sent starting pitcher Zane Smith to Pittsburgh for Willie Greene, Scott Ruskin and a player to be named later.
That player would be Moises Alou.
Smith would go 6-2 with a 1.30 ERA the rest of the way, helping the Pirates win the NL East, though they would lose four games to two in the NLCS against the Reds. He would remain in the rotation the next several years, helping them again to the division title and NLCS before losing there in 1991 and 1992.
Alou would enjoy a 17-year career, hitting .303/.369/.516 with 421 doubles and 332 homers. He made the postseason four different times, winning the World Series in 1997. He did none of this with the Expos, though.Credit: Getty Images
12. Tigers grab future postseason hero
The Tigers grabbed Delmon Young on Aug. 15, 2011 from the Twins for Cole Nelson and a player to be named later (Lester Oliveros). Though Young didn't remain with the Tigers for long or have a great run there, he did make a huge impact when it mattered.
The 2012 ALCS saw Young hit .353/.421/.765 with two homers and six RBI, taking the series MVP as the Tigers won the pennant.Credit: Getty Images
11. Padres pay big for Giles
On Aug. 26, 2003, an established star was traded from one non-contender to another.
The Padres acquired Brian Giles -- who was hitting .299/.430/.521 at the time -- for Jason Bay, Oliver Perez and a player to be named later (Cory Stewart).
It ended up being a hefty price to pay, though it worked out OK. The Padres would make the playoffs in both 2004 and 2005 with Giles as one of their offensive centerpieces.
Meantime, Bay won Rookie of the Year in 2004 and was a very productive slugger for a half-decade. Perez had one great season before falling apart, though he's still hanging on as a reliever more than a dozen years later.Credit: Getty Images
10. Pirates give up on Joey Bats
The Pirates originally had Jose Bautista, but lost him in the Rule 5 draft in 2003. They had him back after a 2004 trade until Aug. 21, 2008. That's when the Pirates dealt him to the Blue Jays for a player to be named later, who would turn out to be Robinzon Diaz.
Diaz appeared in 41 games for the Pirates in 2009.
Bautista would end up being one of the best sluggers in Blue Jays history (he's second to Carlos Delgado in homers for the franchise), finishing in the top eight of MVP voting four times.Credit: Getty Images
9. Rockies deal Walker
Larry Walker spent nearly 10 seasons in Colorado as a fixture for the slugging Rockies. He made four All-Star teams, won five Gold Gloves, two Silver Sluggers and an MVP.
On Aug. 6, 2004, however, the franchise moved on, dealing Walker to the Cardinals for Jason Burch and two players to be named later. Those players would be Luis Martinez and Chris Narveson.
Walker would hit .286/.387/.520 in 144 games for the Cardinals in two seasons. He hit six home runs in the postseason as the Cardinals made it to the World Series, but they were swept by the Red Sox. They made the NLCS the next season, but lost to the Astros. Those would be the longest postseason runs in Walker's career.Credit: Getty Images
8. Red Sox acquire Dave Henderson
It was Aug. 19, 1986 when the Red Sox made a deal that would help them advance to the World Series.
The Red Sox sent Rey Quinones, players to be named later (Mike Brown, Mike Trujillo and John Christensen) and cash to the Mariners for Spike Owen and Dave Henderson.
"Hendu" would end up hitting a series-saving, ninth-inning, two-out, two-run, game-tying home run in Game 5 of the ALCS before the Red Sox took Games 6 and 7 to advance to the World Series.Credit: Getty Images
7. Harvey's Wallbangers grab a Hall of Famer
It was Aug. 30, 1982 when the Milwaukee Brewers acquired Don Sutton from the Astros for players to be named later (Kevin Bass, Frank DiPino and Mike Madden) and cash.
Sutton would help lead those Harvey's Wallbangers Brewers to the only pennant in the history of the franchise. He was the winning pitcher in Game 3 of the ALCS.Credit: Getty Images
6. Twins get Blyleven back
Bert Blyleven spent the first six and a half years of his career with the Twins, but he had been gone for almost a decade when the Twins got him back.
It was Aug. 1, 1985 when the Indians sent Blyleven to Minnesota in exchange for Jay Bell, Curt Wardle, Jim Weaver and a player to be named later (Rich Yett).
In his second Twins stint, Blyleven was good but not great, though he was good in two starts in the 1987 World Series, which the Twins won.Credit: Getty Images
5. Braves load up with Neagle
It's rare to see a mid-prime talent like Denny Neagle traded in August, but that happened in 1996, when the Pirates sent Neagle to the Braves for Corey Pointer, Ron Wright and a player to be named later (interestingly, the stellar Jason Schmidt).
Neagle finished eighth in NL Cy Young voting that season. In 1997, he went 20-5 with a 2.97 ERA and finished third. He started eight times in the postseason for the Braves, helping them win the 1996 NL pennant.
As alluded to earlier, Schmidt went on to have a very good career, though his best years didn't happen with the Pirates but instead the Giants.Credit: Getty Images
4. Mets deal Cone for Kent
On Aug. 27, 1992, the Mets traded All-Star starting pitcher David Cone and ended up getting a gem in return.
Cone went to the Blue Jays, where he'd help them win a World Series ring before hitting free agency and signing with the Royals. The Jays would repeat in 1993 and Cone would end up winning four more rings -- with the Yankees.
Meantime, the Mets got back a young second baseman by the name of Jeff Kent. He would spend parts of five seasons with the Mets, though the club never made the postseason. As we know, Kent ended up with an excellent career and he remains on the Hall of Fame ballot (he got 16.7 percent of the vote last season, his fourth year on the ballot).Credit: Getty Images
3. The Jeff Bagwell Trade
A deal that went down in baseball infamy and served as a cautionary tale for years when it came to coughing up prospects, the Jeff Bagwell trade happened in August.
On Aug. 30, 1990, the Red Sox coughed up the future Hall of Famer when he was just a Double-A first baseman for relief pitcher Larry Andersen. Andersen would pitch to a 1.23 ERA and 0.96 WHIP in 15 appearances the rest of the way, but the Red Sox were swept in the ALCS and then Andersen signed with the Padres in the offseason.Credit: Getty Images
2. The John Smoltz Trade
We can't mention Bagwell without Smoltz. These are the two deals people most often mention in baseball history where a contender gave up a prospect that cost them dearly in the future.
Smoltz was traded by the Tigers to the Braves on Aug. 12, 1987 for starting pitcher Doyle Alexander.
Alexander would actually go 9-0 with a 1.53 ERA in 11 starts down the stretch, helping lead the Tigers to 98 wins and the AL East title. Alas, they were taken down four games to one by the inferior Twins in the ALCS. Alexander would go 20-29 with a 4.38 ERA the following two seasons with the Tigers missing the playoffs.
Smoltz would go on to a Hall of Fame career, pitching in 13 different postseasons for the Braves, winning five pennants and one World Series.Credit: Getty Images
1. The Dodgers-Red Sox blockbuster
One of the biggest deals in MLB history happened on Aug. 25, 2012, when the Red Sox shipped Adrian Gonzalez, Carl Crawford, Josh Beckett and Nick Punto to the Dodgers for Ivan DeJesus, James Loney, Allen Webster and players to be named later Rubby De La Rosa and Jerry Sands.
The Red Sox saved loads of money and used some of that to acquire players and win the 2013 World Series.
The Dodgers won the NL West the following four (and soon to be five) seasons.Credit: Getty Images