1. Don August and Mark Knudson for Danny Darwin
By far, the most important August trade ever to take place was the August 15, 1986 deal sending Danny Darwin to the Milwaukee Brewers for Mark Knudson and… Don August. There are plenty of trades that happen in August, but how many of them actually involve an actual August?
August was the Brewers' Opening Day starter in 1989 (know who else started on Opening Day that year? Jack Morris!) and went 34-30 with a 4.64 ERA in parts of four seasons for the Brew Crew. Darwin was a bullpen acquisition for the Astros for their stretch run, although he didn't appear in the 1986 NLCS. He did, however, pitch in 21 major-league seasons (1978-1998). —Russell Carleton
2. Carl Pavano
After August, the 2009 Twins were just 53-56, in third place, and starting to fade again in the AL Central, 5.5 games back of the division-leading Tigers. They were trying to make a go of a rotation of Nick Blackburn, Scott Baker, Francisco Liriano, Glen Perkins, and Anthony Swarzak, who had combined for a 4.92 ERA on the year to that point. So Bill Smith made the first (and really, the only) truly good deal of his GM career, getting Carl Pavano from the Indians for minor-league control specialist Yohan Pino.
Pavano was not great down the stretch, but compared to what came before, he was a revelation. The Twins lost only four of his 12 starts, and he pitched fewer than six innings in just three of them, sparing the bullpen and providing stability for a team that had had none. Pavano started, and won, game 162 over the Royals, putting the Twins in a tie with the Tigers at the end of the regular season. The Twins won that game before losing to the Yankees (of course), in three games. After the season, they offered Pavano arbitration and he accepted, which turned out to be one of the best accidental decisions in Twins history. Pavano (and his mustache) would lead the AL in complete games and be the club's workhorse throughout their terrific 2010 season. And that, my friends, is why August matters. —Michael Bates
3. Cody Ross
When the Giants claimed Cody Ross off waivers on August 22, 2010, there was little fanfare around the move, and rightfully so. As a member of the Marlins that year, he epitomized the league-average hitter. Seriously, the league average slash line and wOBA in 2010 were .257/.325/.403 and .321, Ross' line and wOBA were .265/.316/.405 and .319. He offered some outfield defensive versatility as he could fake it a bit in center field, but he was really better-served in a corner-outfield spot. Ross would play in 33 games for the Giants during the regular season, accumulating 82 plate appearances in which he hit .288/.354/.466. Definitely a solid line, but if that's where the story ended, he wouldn't be one of the more memorable August acquisitions of all-time.
In the National League Division Series Ross had a big series deciding Game Four. He drove in the Giants first run smacking a home run, and eventually singled in the game-winning run in the seventh inning. His play in the NLDS would serve as the appetizer for the eventual main course, which would be served in the National League Championship Series.
Ross went nuts in the NLCS. In 23 plate appearances, he hit .350/.435/.950 with three home runs. That's right; he slugged .950. He opened the series by leading the Giants to a 4-3 win over the Phillies, drilling two home runs off Roy Halladay. He stayed hot in Game Two (which the Giants lost), whacking his third home run of the series, this one off Roy Oswalt. Ross didn't find the seats in Game Three, but he did drive in the first run of the game, which the Giants eventually won 3-0. He was relatively quiet the rest of the series, but the damage he had already done at the dish was enough to earn him NLCS MVP honors. He had a solid World Series, but it is his play in the NLCS that Giants fans will always remember. —Josh Shepardson
4. Zane Smith
The 1990 Pirates, much like this year's version, were a young team on the upswing. Just five years after the franchise nearly left town, the Pirates were Pittsburgh's darlings, led by such rising stars as Barry Bonds, Bobby Bonilla, Andy Van Slyke and Doug Drabek. However, there was still lingering doubt in the Pirates' clubhouse about their chances of beating out the established powerhouse New York Mets for the National League East title as the season entered its final third.
Then the Pirates traded with the Montreal Expos—remember them?—for left-hander Zane Smith on August 8. Smith went 6-2 with a 1.30 ERA in 11 games, including 10 starts, down the stretch. Most importantly, Smith threw a one-hit shutout as the Pirates beat the Mets in an epic 1-0 game in the opener of a twi-night doubleheader on September 5. Smith gave up a leadoff single to Keith Miller in the top of the first inning and that was it. Bonds won the game with a bases-loaded single off John Franco in the bottom of the ninth and the crowd of 49,793 made so much commotion that I feared the concrete bowl at confluence of the Allegheny, Monongahela, and Ohio rivers might collapse. The Pirates swept the twinbill with a 3-1 win in the nightcap and never looked back on their way to their first division title in 11 years. Five years after being on life support, the Pirates were relevant again the August trade for Smith was a big reason why. —John Perrotto
5. Doyle Alexander
On August 12, 1987, the Detroit Tigers sat in a tie for second place with the New York Yankees, 1.5 games behind the AL East-leading Toronto Blue Jays. They sought statrting pitching help for the stretch drive and found a willing trading partner in the Atlanta Braves, who were nine games back in fifth place in the NL West. The Tigers acquired crafty veteran right-handed starter Doyle Alexander. In exchange, the Tigers surrendered a 20-year-old starter who had struggled to a 4-11 record with a 5.73 ERA while splitting time between Double- and Triple-A.
Over 11 starts down the stretch, Alexander would go 9-0, with a minuscule 1.53 ERA, helping to propel the Tigers to the AL East title. The stellar performance, despite being only 11 starts, was good enough to earn Alexander a fourth-place finish in the AL Cy Young voting. Unfortunately, with the end of the regular season came the end of Alexander's magical run. In two starts in the ALCS, Alexander was 0-2, surrendering 10 runs over nine innings. The Tigers fell 4-1 in the ALCS to the eventual World Series champion Minnesota Twins. Alexander would make the All-Star team in '88 before stumbling to a 6-18 record in the 1989 season, which was his last.
Now, one could argue—and rightfully so—that the Tigers got just what they were looking for, and probably more, in Alexander. However, history tends to forget Alexander's amazing pennant-race performance and regards this as an incredibly lopsided trade in the Braves' favor. Why? That young right-hander the Braves acquired in return was none other than John Smoltz.
Smoltz would join the Braves' rotation in 1988, starting a career that spanned 21 seasons (20 in a Braves uniform). During his career, Smoltz recorded 213 wins and 154 saves, helping the Braves to 14 division titles, including a World Series victory in 1995. He is regarded as one of the great big-game pitchers, based his 15-4 record in post-season play. Smoltz was an eight-time All-Star and a Cy Young Award winner in 1996. A future Hall-of-Famer, he is 13th among all-time career leaders in pitching WARP.
All in all, this was an August trade that paid short-term dividends to the Tigers, but even bigger long-term dividends to the Braves. —William Skelton
6. Larry Anderson and Jeff Bagwell
The Boston end of this trade is often cited as among the worst or most lopsided "deadline deals" in history. And it certainly is that, but I think that when most people hear that, they've got the wrong deadline in mind. The traditional "trade deadline" was long past when this trade was completed at the end of August, just ahead of the waiver deadline, making the deal even more difficult to comprehend from Boston's side—they were paying for one month of a short reliever, not two. They got 22 innings out of Andersen, and for that they gave up the guy whose path to becoming an all-time top-five first baseman would begin the very next season.
There are mitigating factors here. For one thing, there can be no doubt that the Sox sorely needed relief help—aside from Andersen and part-time closer Jeff Reardon, no reliever threw 20 or more innings for the team in 1990 with an ERA+ above 92—and Andersen was one of the best, having emerged from obscurity at age 33 to post a 2.57 ERA and 141 ERA+ in parts of five seasons with the Astros, including a 1.95/191 up to that point of 1990. Indeed, there's a reasonable chance that Andersen was the difference between winning and losing the American League East in 1990; though the Sox were up 6.5 games on the Jays at the time the trade was made, they slumped badly after that and were caught by the Jays three times between August 30 and the end of the season, even falling behind by as many as 1.5 games on September 25 before winning six of their last eight and finishing on top by two. Andersen pitched brilliantly, and in high-leverage situations, throughout that period, was worth 0.9 WARP, a tremendous figure for 22 innings of relief work.
Also, Bagwell was a nice prospect in the midst of a breakout year, but had never before been ranked in Baseball America's top 100 (he'd debut at No. 31 in 1991), and while he'd played third almost exclusively in the minors, he would never play an inning there as a big-leaguer, and the Sox had to have some idea that that wouldn't stick. The organization already had Mo Vaughn, the 1990 76th-best prospect who would enter 1991 all the way up at 10th-best, apparently ready to take over at first base. You might forgive an organization who badly needed an elite reliever for being willing to give up a heretofore non-top-prospect prospect who was blocked within the organization at his best position, if it meant getting one of the best relievers in the game.
You might… but we probably shouldn't. The Red Sox, while they won the AL East, simply weren't very good—their 88-74 record would have placed them third in the West, and closer to the last-place Twins than the first-place, 103-59 A's—and were somewhat predictably steamrolled by those juggernaut A's in a four-game ALCS sweep (Andersen appeared in three of those games, and fared no better than any other Sox pitcher did), so even if acquiring Andersen did buy them their playoff appearance, query how much that appearance was realistically going to be worth. And, of course, there's just no ignoring the reality of the situation: In exchange for 22 very good innings in September, the Sox parted with a breakout prospect who would immediately win the other league's Rookie of the Year Award, and then become one of the very best players in that league every year for the next 10 (never dropping below 5.0 WARP from 1992-2001) and one of the greatest first basemen the game has ever seen. It cost the Astros a lot more than just Andersen to keep Bagwell with the team throughout all that, of course, but it was Andersen who made any of it possible in the first place. The Andersen-for-Bagwell swap was one August trade that mattered, and kept on mattering for more than a decade. —Bill Parker
7. Woody Williams
This trade nearly didn’t qualify for our list, because on July 31, 2001, the Cardinals nearly traded Ray Lankford to San Diego for Woody Williams. Two days later, the teams consummated the deal, and the veteran Williams found a home in St. Louis.
On the day he was acquired, St. Louis sat in third place, 7.5 games behind the Cubs in the NL Central and five back of the Diamondbacks in the wild card. Faster than you could say Doyle Alexander, Williams won seven of his eight decisions by posting a 2.28 ERA, completing three games, and garnering nearly a half win more of WARP in his 11 starts than he did in San Diego.
The Cardinals ended up tying for the division, and as the wild card, lost to Arizona in a thrilling five-game NLDS. But Williams' value went beyond just August and September of 2001. The Cardinals went on to make the playoffs in three of his four seasons in St. Louis, missing only in his 4.9 WARP year of 2003—a year in which he won a career-high 18 games. He eventually started Game One of the 2004 NLCS and Game One of the World Series that year, where he was tagged for seven earned runs in 2.1 innings pitched.
Williams left St. Louis after 2004, and at ages 38 and 39 continued to be effective, starting post-season games for the Padres in both seasons before retiring with Houston in 2007. —Mike Ferrin