1. The Tigers Trade John Smoltz to the Braves for Doyle Alexander
Granted, I was four when this trade happened, so the specific transaction was not traumatic. I remember less about the Tigers' 1987 pennant than any one of several games of tiddlywinks with my grandmother. But consider how it shaped the course of both teams in my formative baseball years. John Smoltz turned into John Smoltz and I turned into a brief bandwagon Braves fan during the early '90s, as everyone did. Meanwhile the Tigers didn't have Smoltz in their rotation, taking away one more reason to stay a fan of this team. That pared the list down to: they were close and accessible and I lived in their Triple-A town.

No, the trade didn’t make or break the Braves. But they got John Smoltz, along with all the other pitchers. I got the tapering years of Gullickson/Tanana and something called "Brian Moehler."

Once again—and this is for all the general managers who are dads out there—before making a deadline trade, consider the children. My son deserves to grow up watching Steven Moya mash home runs in Comerica Park, and this year’s middle relief will get better. —Matt Sussman

2. The Dodgers Trade Pedro Martinez to the Expos for Delino DeShields
I don't know that the Delino DeShields/Pedro Martinez swap meant that much to me at the time, though as a Dodger hater in the 1990s, it certainly didn't hurt that they were the team getting snookered. But we didn't know they had been snookered at the time. At the time, this was just an incredibly interesting deal, two players so young and so attractive that you couldn't even trade for their baseball cards. I was so interested in it that I went out and got the Sports Illustrated issue with Tim Kurkjian's article on the trade. That piece had so much more than I was used to getting from my daily newspaper:

Quotes with real color. ''Even if we'd had five strikes against him, we couldn't have hit him," said Rich Donnelly about Pedro.

Interesting research: "Reviewing all trades made in the last quarter century, one finds that there was not a one-for-one deal involving proven major leaguers age 25 and younger rivaling this one in terms of talent and potential. On Dec. 8, 1977, the California Angels dealt second baseman Jerry Remy to the Boston Red Sox for pitcher Don Aase, and on Oct. 18, 1973, the Pittsburgh Pirates sent second baseman Dave Cash to the Phils for pitcher Ken Brett. None was older than 25 and all were good players at the time, but neither deal was on a par with DeShields for Martinez."

Backstory: "The roots of this trade reach from May 1992 when DeShields was in a batting slump and L.A. prospect Eric Karros wasn't getting much playing time at first base. The Dodgers did some research on DeShields in contemplating a possible swap, but within a few weeks DeShields got hot while Karros moved into a starting role and was on his way to becoming the National League Rookie of the Year. Then, at the end of last season, Montreal began looking around. The Expos needed a righthanded starter, and they also had to move a high-salaried player if they wanted to keep their 1994 payroll under $20 million. DeShields was coming off a .295 season, and with Mike Lansing (.287 as a rookie) a suitable eplacement, the Montreal brass decided DeShields was their most marketable asset."

Pedro: "Now he wants so much to remain in Montreal that he says his goal in 1994 'is to marry a French Canadian woman.'''

I enjoyed that article so much that I started hoarding SI whenever I could find it–granddad's house, dentist's office, etc. Before long, I was subscribing. That was a trade with a clear winner. (Me. I was the winner. In case that was too subtle.) —Sam Miller

3. The Indians Trade Joe Carter to the Padres for Sandy Alomar, Carlos Baerga, and Chris James
The 1980s ended for the Cleveland Indians a couple of weeks early. On December 6, 1989, the Indians traded the man who had become the "face of the franchise," Joe Carter, to the San Diego Padres. It was devastating because Carter was always good for 30 HR and 100 RBI (I was younger then). He was one of the last pieces left from a young core that once looked so promising that Carter and Cory Snyder were featured on the cover of Sports Illustrated proclaiming them the soon-to-be 1987 World Series champions (whoops). And then Carter was gone. I heard he popped up later with the Blue Jays and did something or other, which is nice for him.

Despite how sad it was to see Carter go, the trade did net the Indians Carlos Baerga (back when he was good) and Sandy Alomar Jr. As an added bonus, they also got Chris James, who is still the answer to an Indians trivia question for once driving in 9 runs in a game. If trading Carter was the symbolic statement that the 80s were over for the Indians, then in retrospect, that was also the day that the 90s began. At the time, we had no idea how much fun the 90s would be in Cleveland. Alomar and Baerga would go on to develop into solid, middle-of-the-diamond players and eventually, part of the first Indians team to make the World Series in 41 years. At the time though, it hurt. My brother had a Joe Carter Starting Lineup figure, and it's not like you could change the jerseys on those things. Other players had come and gone, but Carter? Now that figurine was now just an echo of the glory that once was. Looking back—oh dear, I think I'm about to go all Wonder Years on you—it was the first time I had experienced the transition from one era to another in my fandom and for a kid, that's always a little traumatic. The Indians teams that followed gave Cleveland (and me) some magical memories, but that day in December of 1989 turned out to be one of those strangely formative moments in life. —Russell A. Carleton

4. The Braves Trade Brett Butler, Rick Behenna, and Brook Jacoby to the Indians for Len Barker
Brett Butler was the first minor-league player I ever saw who had the unmistakable skills and aura of a future big-leaguer. He played part of the 1980 season for the Durham Bulls, Atlanta’s High-A farm team, producing a .366/.513/.513 slash line and stealing 36 bases in 66 games. In fairly short order, he was in the majors. In my youthful conception of the natural order of things, he would be the Atlanta Braves’ center fielder and leadoff sparkplug thereafter, until his wheels someday fell off.

Then, pow: After the 1983 season, Butler was traded, along with Brook Jacoby and Rick Behenna—who had thrown a no-hitter in Durham in that same 1980 season—for Len Barker. Butler and Jacoby were PTNBLs two months after the deal was made; the Braves had thrown in an additional $150,000 in late August, when they acquired Barker to help them in the stretch run (they fell short, missing the playoffs).

Barker himself had thrown a big-league perfect game in 1981, when he was an All-Star, but the trade rattled me. Just like that? Butler gone? And Jacoby, who had been so highly regarded in the minors that he skipped high-A Durham altogether? I had thought of the minors as a place with more sanctity than that, where the assets were prized and protected. These were the Braves’ guys, stocks just starting to pay off. How unceremoniously they could be flipped.

Having finally accepted the trade (and appreciating that Barker was a pitcher of no small talent), I then felt the second shock of the deal: the Braves had made a bad one. Butler became one of the game’s premiere leadoff hitters for a decade, and Jacoby was an All-Star, locking down third base for the Indians for the rest of the 1980s. Len Barker was done as a Brave—and, effectively, as a ballplayer—by the end of 1985. —Adam Sobsey

5. The Yankees Trade Rickey Henderson Back to the Athletics for Luis Polonia, Eric Plunk, and Greg Cadaret
It was June 21, 1989, when Rickey Henderson came back home. The Oakland native had come up through the Athletics' system and flourished at the Coliseum in the early 1980s, but he had spent the previous four-plus seasons playing in pinstripes. The A's were coming off of a World Series appearance the previous year and were heavy favorites to repeat in the American League West, sitting 17 games over .500 when they siphoned soon-to-be free agent Henderson from the Yankees in exchange for speedster Luis Polonia and a pair of relief pitchers.

I knew of Rickey's legend, but his playing for the local nine meant that I could witness the Rickey Show first hand. He made quite an impression on a nine-year-old kid who was in the early stages of baseball addiction, and I immediately identified with him as the rare big-leaguer who threw lefty yet batted right-handed, just as I did, and whose greatest asset was his speed on the basepaths. Rickey made baserunning look more fun than hitting, a seemingly impossible concept for a nine-year old to fathom.

Henderson was a spark plug atop the A's order for the rest of that season, and he virtually carried the team offensively in the playoffs. He won MVP honors in the ALCS versus Toronto and continued rolling through the World Series sweep of the cross-bay Giants. His combined numbers for the '89 postseason include a .441/.568/.941 line with 12 runs scored, eight extra-base hits (including three homers), and 11 steals in 12 attempts, all in just nine games. The A's would go on to sign Rickey to a lucrative free agent offer in the off-season, retaining his services and his swagger, and Rickey responded with the best season of his career, culminating in the 1990 AL MVP award and yet another World Series birth. Rickey is responsible for copious memories of my youth, but what I remember most is not the crouched stance, the “I am the greatest” speech, nor the fluorescent-green Mizuno batting gloves that were too expensive for my allowance; what I remember most is how he helped to enhance my enjoyment of the game, whether from the stands, on the field, or reading the sports section of the newspaper each morning. —Doug Thorburn

6. The Rays Trade Fred McGriff to the Cubs for Manny Aybar and Jason Smith
At one point during the McGriff-to-Chicago talks, a local sports reporter threw out the name Julio Zuleta as part of a potential package. Zuleta, forgotten by now, was popular at the time because he practiced "voodoo" in the dugout by setting bats on fire during a slump. Unfortunately when the trade happened, Zuleta was nowhere to be found. Aybar and Smith went on to do nothing for the franchise, and while Zuleta would've been more of the same, at least he would've made things a little more entertaining—sort of like Jonny Gomes. The important childhood lesson learned? Never get your hopes up over trade rumors. —R.J. Anderson

7. The White Sox' White-Flag Trade With the Giants
A lot of people my age cite the players strike of 1994 as the moment their baseball innocence was lost forever, as a sea of cynicism took the place of what was once youthful excitement and unconditional love of the game. I was too stupid to give in to that; my fandom remained intact well after the strike. No, for me the earth-shattering move that shaped my baseball mind for years was the infamous white flag trade between the White Sox and the Giants. I was 11 at the time and very much in love with Wilson Alvarez, the left-handed power pitcher whose obvious talents obfuscated his flaws in my immature mind. He threw a no-hitter once (I totally don’t remember it), and that’s all I cared about. The White Sox were a scant 3 1/2 games out of first place when they traded Alvarez, Danny Darwin, and Roberto Hernandez for Keith Foulke, Bob Howry, Lorenzo Barcelo, Ken Vining, Brian Manning, and… Mike Caruso. I didn’t recognize any of the names the White Sox got back, and I threw a tantrum fit for YouTube. Youthful naivete was replaced by a bitter heart in the short term, but eventually that was similarly replaced by a deeper understanding of prospects and players from other organizations in general, as the White Sox would end up winning the division in 2000 on the backs of some of the players they traded for.

Sure, they straight-up lied to me about Mike Caruso, but in the end they knew what they were doing, even if 11-year-old Mauricio vehemently disagreed. —Mauricio Rubio

8. The Red Sox Trade Nomar Garciaparra to the Cubs in a Four-Team Deal
Yankee Empire ownership of Red Sox Nation peaked on July 1, 2004. That year, the Yankees were still riding high on the dramatic close to the 2003 ALCS. And on that day, the Yankees completed a three-game sweep of their arch-rivals in extraordinary fashion, to go to a 50-26 record—eight and a half games over Boston. The game went into extra innings, tied at 3-3. Derek Jeter infamously dove into the stands to retire Trot Nixon in the top of the 12th He had to be removed from the game, and Gary Sheffield wound up playing third base while DH Bernie Williams moved to center and the Yankees lost their DH slot. Manny Ramirez homered in the 13th to put the Sox ahead, but the unlikely trio of Ruben Sierra, Miguel Cairo, and John Flaherty got consecutive hits in the bottom half to walk off with a win.

For Red Sox management, enough was enough. They noticed the dramatic contrast between Jeter’s heroics and, on the other hand, their own star shortstop. Nomar Garciaparra did not play in that July classic. He was resting from an Achilles’ injury, and his absence from such an important battle compounded the ugly, nagging question of his contract extension. Garciaparra was a superstar in New England—he had five seasons of at least 6.0 WARP in six years—and he wanted to be paid like it.

But Theo Epstein and his bosses didn’t feel like they needed to sue for Garciaparra’s loyalty. The team didn’t lack for offense (Manny Ramirez, David Ortiz, Kevin Millar), starting pitching (Pedro Martinez, Derek Lowe), or fan favorites (Ramirez, Ortiz, Johnny Damon). What they needed was a healthy contributor at shortstop who could help the Red Sox finally get a World Series title in 2004. Theo said in announcing the deal, “If there was a flaw on this club, it was that the defense on this team was not championship-caliber," Epstein said. "We might have gotten to the postseason. But, in my mind, we weren't going to win a World Series with our defense the way it was.” So, in a four-team deal, Garciaparra was shipped off to the Cubs while the Sox received Orlando Cabrera from Montreal and Doug Mientkiewicz from Minnesota—both of them Gold Glove winners.

As a Yankee fan of 15, I took it as a sign that the Red Sox wouldn’t be serious contenders to the Yankees. Yankee dominance would remain eternal. Why would a contending club trade away one of its most recognizable and talented players mid-season? But, as it turned out, the removal of “NOMAH” was actually a blessing for Boston. The team went 42-19 the rest of the year, and Cabrera tacked on 151 points to his OPS at his new home. He also hit .379 and had five RBI in the infamous 2004 ALCS against the Yankees. Boston ice cream chain JP Licks renamed its “Cherry Garciaparra” flavor “Cherry Ortiz,” and all of a sudden the Red Sox became a juggernaut. —Dan Rozenson

9. The Reds and Yankees Swap Roberto Kelly and Paul O'Neill
I wasn’t yet paying attention to baseball on November 3, 1992, when the Reds sent O’Neill and minor-league first baseman Joe De Berry (who never made the majors) to New York for Kelly, who had been one of the few bright spots on the Yankees’ early-90s tire-fire teams and an All-Star in the preceding season. Kelly, who had been regarded as an untouchable part of the Yankees’ outfield future not long before, had been displaced in center by Bernie Williams, and O’Neill had earned a reputation as one of the best defensive right fielders in baseball. Both players were coming off disappointing offensive seasons, but the Yankees liked the way O’Neill’s left-handed swing suited their stadium. Still, the trade was a gamble, as Yankees GM Gene Michael acknowledged: O’Neill was a year and a half older and to that point had been worth 9.1 WARP to Kelly’s 12.6.

After his age-27 swan song in the Bronx, Kelly had his uses but became a journeyman, roaming from the Braves to the Expos, Dodgers, Twins, Mariners, Rangers and, finally, back to the Yankees, for whom he played 10 games in April of 2000. He surpassed 500 plate appearances in only one subsequent season. O’Neill, free of Reds skipper Lou Piniella’s needling and fixation on turning him into a pull-happy power hitter, blossomed into a batting champion and an on-base threat and remained productive into his late 30s. Along the way, he became a classic example of a player who’s beloved at home and hated everywhere else: Yankees fans interpreted his tantrums as the byproduct of his will to win, while everyone else (including Piniella) called him a crybaby. His batting stance and home run stroke are burned into my brain; I’m still trying to make that left-handed toe tap, leg kick, and level swing look anywhere close to as cool from the right side of the plate.

“Everybody hears the horror stories,” O’Neill said about playing in New York, at the time of the trade. “I hope there are some good ones too.” As a Manhattan kid living a few subway stops from the Stadium in the mid- to late-90s, I got to savor more than my fair share of good sports stories. And in many of them, O’Neill played a central role. —Ben Lindbergh

10. The Yankees Acquire Tim Raines for Blaise Kozeniewski
The Core Four/Fab Five deserve (and receive) much of the credit for the Yankees’ late-90s success, but complementary pieces like Raines, Chili Davis, and Darryl Strawberry played an important part in elevating those teams to dynasty status. By the time Raines reached New York in 1996, his body was brittle, and he had little value outside of the batter’s box. In a part-time role, though, he was about as good as bench guys get. Platooning with Chad Curtis, Ruben Sierra, and Mark Whiten sheltered Raines from left-handed pitchers (particularly in ’96 and ’97) and helped him post a combined .293 TAv in three seasons as a Yankee, just one point off his career average. The trade worked out well for everyone except the White Sox: I got to see a great player who still had something left; the Yankees got 4.5 WARP for $5.1 million and a pitcher who never made it past Double-A; and Raines got to wear two World Series rings. —Ben Lindbergh