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​1. Pirates Acquire RHP George "Doc" Medich at the 1975 Winter Meetings
Christmas came exactly two weeks early for me as an 11-year-old in 1975: On December 11, the Pirates acquired right-hander George "Doc" Medich in a trade from the New York Yankees. The Pirates gave up a lot to get the 6-foot-5 Medich, sending away two right-handers who had pitched in All-Star Games, Dock Ellis and Ken Brett, along with a young second baseman of considerable promise named Willie Randolph. Medich was a bit of a mythical figure where I grew up, north of Pittsburgh in Beaver County. He had starred as a baseball and football player at Hopewell High School—noted most as the alma mater of Heisman Trophy winner and Pro Football Hall of Famer Tony Dorsett—then played both sports at Pitt despite carrying the large academic burden of being a pre-med student. He continued to attend medical school after breaking into the major leagues with the Yankees in 1972 and eventually became an orthopedic surgeon.

Medich had an outstanding rookie season with New York in 1973 when he went 14-9 with a 2.95 ERA in 34 games, 32 of which were starts. In 1974, he won 19 games—remember, wins were the accepted measurement of a pitcher's effectiveness back in the unenlightened era—and pitched 279 2/3 innings. He slipped to 16-16 in 1975, but the Pirates were sure the 27-year-old was just coming into his prime and ready to help front their rotation. Sadly, it didn't work out; he was 8-11 with a 3.52 ERA in 1976, then dealt to the Oakland Athletics in spring training the following year as part of a 12-player trade in which the Pirates gave up an outfielder of considerable promise named Tony Armas and got back Phil Garner. The most notable moment of Medich's career with the Pirates came on Opening Day at Veterans Stadium in Philadelphia, when he jumped into the stands and saved the life of a man having a heart attack. That was certainly more important than anything he ever did on the field during an 11-year career that was spent with seven teams. However, from a baseball standpoint—and an 11-year-old kid standpoint—he was a big-time disappointment. —John Perrotto

2. Indians Sign "Black" Jack McDowell Prior to the 1996 Season
Before the 1996 season, the Indians signed "former Cy Young Award winner and two-time 20-game winner" Jack McDowell. Apparently, that was his given name. In '95, the Indians had come oh-so-close to winning their first World Series since the Truman administration, and did it with the ageless Dennis Martinez and Orel Hershiser at the top of the rotation. Perhaps you don't remember the 1996 world champion Indians as well as I do, primarily because they won that World Series in my head prior to the season getting underway.

I remember that when it was all done, the deal was seen as a bust. McDowell went 13-9 in 2006 with a 5.11 ERA. In retrospect, his peripherals weren't horrible (4.30 FIP), but they were not Cy Young-worthy, either. In 1997, McDowell got hurt, demoted to the bullpen, and never really surfaced again. By 1999, he was out of baseball. It was a lesson in the realities of pitching. As a Cleveland fan and a teenager, I believed in the magic of "knowing how to win" because of those 20-win seasons. I didn't appreciate that a pitcher is a risky signing no matter what, because they get hurt… just because they are pitchers. I was in high school at the time, which is when you discover that life doesn't work in magical ways, no matter how much you want it to. Jack McDowell was just one of those lessons on how baseball will break your heart. —Russell A. Carleton

3. Yankees Trade Jeff Weaver to the Dodgers
To a preteen and teenage me, watching Jeff Weaver pitch was the equivalent of picking scabs over and over again, then filling the bloody wounds with salt and rubbing alcohol. The Yankees had dealt one of my favorite starters, Ted Lilly, as part of a three-team trade to acquire Weaver during the 2002 campaign, so I might have been predisposed to dislike the righty. Even so, his 2003 season didn't earn him any brownie points: In just 159 1/3 innings, Weaver somehow managed to allow 211 hits and 113 runs (106 earned), good for a 5.99 ERA. Granted, his numbers were inflated by a .343 BABIP, but I was still shocked to find that Weaver registered a 4.32 FIP and 1.7 WARP in 2003.

However, what left the worst taste in my mouth was his World Series performance. Though Weaver hadn't pitched in 11 days, manager Joe Torre brought in the northpaw during a tied game. After emerging from one inning unscathed, Torre pressed his luck and sent Weaver out for a second inning of work. He promptly gave up a game-winning walk-off home run.

I hoped and prayed that the Yankees would trade Weaver over the offseason, regardless of the return. My wish was granted. In December 2003, the Yankees traded Weaver, Brandon Weeden, Yhency Brazoban, and cash to the Los Angeles Dodgers for Kevin Brown. As it turns out, I owe my thanks to my colleague, Dan Evans, who was the general manager of the Dodgers at the time. Brown proved to be incredibly fragile and a hot head who broke his non-pitching hand punching a clubhouse wall during a September loss to the Orioles, but his inability to stay healthy primed me for the American Idle era. And credit where credit is due: Weaver notched 220 innings and allowed 219 hits, good for a 3.79 FIP and 3.6 WARP, for the 2004 Dodgers. But I salute you, Dan, for ending Jeff Weaver's Yankees tenure. —Stephani Bee

4. Andre Dawson's Blank Check
Andre Dawson didn’t just want to be a Cub. He wanted to be a Cub more than any player in history. A perennial All-Star who, in a 1983 New York Times poll of major-league players, was called the best in the game, Dawson and his bad knees were desperate to get off the turf of Le Stade Olympique.

But the 1986-87 offseason, was the year of collusion. And that, coupled with the Tribune Company’s unwillingness to increase their payroll (read: participation in the conspiracy), Dawson remained unsigned. Despite his near-frantic pleading.

As a 10-year-old, I didn’t understand the dollars and cents; I just thought that Cubs general manager Dallas Green was a fool. Who could possibly think the slugging Dawson, a force at the plate, on the basepaths, and in the outfield was worse than presumed starter Brian Dayett? How could Green, who in three years had done what no Cubs GM had in nearly four decades—put a team in the playoffs—be so wrong?

Dawson was unsigned in March 1987. But rather than biting the bullet and returning to Montreal while sitting out until May, like teammate Tim Raines was doing, Dawson pressed the Cubs. The outfielder and his agent, Dick Moss, showed up in Cubs spring training offering a blank check to Cubs ownership. “Name you’re price, we’ll sign” was the message.

So the Cubs gave Dawson $500,000. Dawson hit 49 homers and won the MVP that year on a typical Cubs team that faded in the final two months. But here was Dawson, a star who wanted to play for my team.

I’m not really a Cubs fan anymore. I don’t have an allegiance. I love good stories and am lucky enough to talk to many current and former ballplayers as part of my job. I always get nervous when I talk to, or meet, Andre Dawson. He was my favorite player growing up. Still is, actually, because despite the fact everyone tried to stonewall him, he got what he wanted in the end. He chose my team, more than they chose him. And I loved every minute of it. —Mike Ferrin

5. Red Sox Sign Manny Ramirez Prior to the 2001 Season
In 2000, free-agent-to-be Manny Ramirez played in only 118 games. He finished sixth in the MVP voting and might have actually deserved it. During his limited playing time, Ramirez hit 38 homers. That was impressive, but not as impressive as his .457 on-base percentage or his .697 slugging percentage. At that point, Ramirez was a soon-to-be 29-year-old with a career line of .313/.407/.592 and 236 homers to his name. He was also a New Yorker in an age of profligate Yankee spending. That the Red Sox would sign the best hitter on the market and one of the best of his generation wasn’t expected, so when Ramirez inked an eight-year, $160 million contract with the Red Sox, who were coming off an 85-win season, expectations were, needless to say, high.

Over seven-and-a-half seasons in Boston, Ramirez hit .312/.411/.588, remarkably similar to his numbers in Cleveland. In the early part of his career as a Red Sox, he became symptomatic of what was wrong with the Dan Duquette administration. Later, he was a vital cog in two Boston world championships. Ramirez’s time with Boston certainly had its turbulence, but the end result of seven All-Star appearances, seven top-10 MVP finishes, and the aforementioned two World Series wins make it difficult to argue the contract didn’t return value. Many times—more than we’d probably like to imagine—the excitement generated by big free-agent signings goes unrequited. In this instance, the Red Sox got more than they paid for, and those of us who cheered the signing didn’t do so in vain. —Matthew Kory

6. Giants Sign Moises Alou Prior to the 2005 Season
My baseball fan experience as a youth was mostly casual, and I didn't wrap myself up in following transactions. By the time I was in middle school, I began following off-season dealings more thoroughly. Because of that, the first off-season deal I remember being really excited about as a Giants fan was the signing of Moises Alou to join his father, Felipe, who was serving as San Francisco’s manager.

I didn't care that Alou was 38 years old. He was a marquee player coming off a year in which he smacked 39 home runs with 106 RBI. He was a heart-of-the-order bat that would join Barry Bonds in carrying the Giants to the postseason, and, hopefully, a World Series title. Obviously this isn't what transpired, but at the end of December 2004, it was very real in my imagination. —Josh Shepardson

7. Giants Sign Mark Portugal Prior to the 1994 Season
The most important thing about Mark Portugal would have been that he had a 101 ERA+ in nine seasons, but at the time the Giants signed him before the 1994 season, the most important thing I could identify about Portugal was how good he was against the Giants. In 17 career starts up to that point, he was 11-2 with a 1.91 ERA in 118 innings against the Giants. He'd even hit half of his career homers against the Giants. I was smart enough to know that the Portugal I had seen so dominant was not the Portugal the Giants would get full-time (though his breakout season the year before—18-4, 2.77—had me pretty excited about a rotation that would include Portugal, Bill Swift and John Burkett at the top. Swift and Burkett had gone 43-15 with a combined 3.24 ERA in 1993. What a rotation! I would have thought, because I had never heard of regression and I had never heard of the mean.), but I was at least thrilled to know that the Giants wouldn't have to face Mark Portugal ever again. That's a couple wins right there! But when God closes a Portugal, he opens a Steve Trachsel (1.20 ERA in 15 innings against the Giants in 1994), or a Steve Cooke (1.29 ERA in 14 innings), or a John Roper (1.38 in 13 innings). Turns out there's always a lousy pitcher ready to make the Giants look hopeless. Portugal had a 101 ERA+ in the first year of his deal. Midway through the second, he was traded. For Roper. —Sam Miller

8. Dodgers Sign Dave Goltz and Don Stanhouse Prior to the 1980 Season
After losing to the Yankees in the 1977 and 1978 World Series, the Dodgers had a terrible—by their standards—1979 season, going 79-83. In an effort to improve for 1980, they signed veteran right-handers Dave Goltz and Don Stanhouse. I was excited because:

a) Goltz had won 20 games for the Twins in 1977.
b) Stanhouse had saved 21 games for the Orioles in 1979.
c) I was 10 years old, so a) and b) seemed more important than they were.

Goltz went 7-11 for the Dodgers. He had a 5.68 ERA at the All-Star break and lost his spot in the rotation. He fared a little better in the second half before getting shelled by the Astros in Game 163, when he got the start over rookie left-hander Fernando Valenzuela. After doing little of consequence the following season, Goltz was released on April 27, 1982.

Stanhouse didn't last as long. He pitched just 25 innings for the Dodgers, most of them terrible. Among other things, he walked 16 while striking out five. He'd walked 51 while striking out 34 a year earlier, so this was nothing new for Stan the Man Unusual.

My view of free-agent signings probably has been warped by the Dodgers' acquisitions of Goltz and Stanhouse. If I haven't gotten over them after 33 years, I doubt I ever will. —Geoff Young

9. Kenny Landreaux
As a Dodger fan in the late 1970s and early 1980s, the Hot Stove didn't hold a whole lot of promise. As Geoff Young noted above, the team's initial foray into the free-agent market via Dave Goltz and Don Stanhouse was a disappointing bust, and subsequent years would be more about who was departing—Davey Lopes, Ron Cey, and Steve Garvey, three-quarters of the longest-running infield that anchored four NL pennant-winners—than who was arriving. Kirk Gibson would be the team's next big off-season splash, but by that time in January 1988, I had turned 18, and my concerns were more about which college I'd attend than who'd play center field for the Dodgers.

Which leaves Kenny Landreaux. The 1980 Dodgers lost a Game 163 play-in to the Astros (a game started by the bust Goltz instead of the rookie Fernando Valenzuela), and it's not unreasonable to think that they would have gotten over the hump with a better center fielder than Rudy Law, a 23-year-old burner who stole 40 bases but hit an offense-deadening .260/.306/.302, with virtually all of his plate appearances coming in the top two spots in the lineup. A change was needed, but it wasn't until the Dodgers acquired Landreaux from the Twins for Mickey Hatcher (a futility infielder favorite) and two other players during spring training in 1981 that they got one.

I knew Landreaux because of his baseball card. I could even, in that primitive era, see that his .281 average, seven home runs, and 62 RBI were superior to Law's numbers (with one homer and 23 RBI), to say nothing of a fu manchu mustache and sideburns that would have done a Civil War general proud. When we heard the news of the trade, my dad asked me for a full report after his pre-dinner nap. I went to my room, pulled out my Who's Who in Baseball 1981, wrote out his basic stats on a notepad as well as whatever I could find via my my stack of Sports Illustrateds (including this feature): the centerpiece of a trade for Rod Carew in 1979, he had put together a 31-game hitting streak the following year en route to an All-Star appearance. I wasn't actually writing paragraphs, and the World Wide Web hadn't been invented yet, but in a way, it was my first blog entry.

For all of my excitement, Landreaux rarely lived up to his promise as a Dodger, as he developed cocaine problems and retained his job more due to organizational inertia than anything else. But even in the strike-torn 1981 season, when he slumped to .251/.297/.367, he did haul in Bob Watson's fly ball to seal the Dodgers' first world championship of my lifetime—ample reward for my excitement. —Jay Jaffe

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For me it was 1977, the year Reggie Jackson signed with The Yankees and "Mr. October" was born.
December 5th, 1990. Pat Gillick sends Fred McGriff and Tony Fernandez to the San Diego Padres for Joe Carter and Roberto Alomar.

Still the most important moment in Blue Jays history.
1990 KC Royals, coming off a 90-win season signed Mark and Storm Davis. Add in a fading Brett and 'Bo Knows' baseball and ... they won 75 games.
"In the early part of his career as a Red Sox, [Manny Ramirez] became symbiotic of what was wrong with the Dan Duquette administration." That's kind of an awesome typo.
Angered over the loss of Burt Hooten, and the dismantling of the Cubs of my youth (Santo to the White Sox, Williams to the As, Fergie to Texas, Kessinger to St. Louis, Hundley and Beckert to San Diego), the Dawson signing remains one of the great mysteries of my lifetime. I agree - he WANTED to be a Cubs player. That was so cool to me. He was there for Boys of Zimmer in 1989, so he was rewarded (somewhat) for coming to Wrigley.

Dawson, as noted, remains larger than life.
For me it was when the White Sox signed Albert Belle. I was in 4th grade and the White Sox were usually bad and losing divisions to the Indians. I remember hearing the news on WWF Raw (hey I liked wrestling at the time) and ran to my dad to tell him. He didn't believe me because of the source.

The following summer I was a kid at the White Sox training camps they had. Chris Snopek was the player who had to show up for the kids and fielded questions in front of everyone. I asked him if Albert Belle was a jerk.
I assume he didn't answer the question?
He just laughed :
Fun read. Nice to know your writers can be "homers" from time to time too. BTW, pretty sure it should read "symptomatic" not "symbiotic" in Matthew Kory's piece on Manny.
Right you are!
Gregg Jefferies, 1994! The only stats I knew of as a 12 or 13 year old were the top 20 or so batting averages in the league, as listed in the Lehigh Valley's newspaper of record, the "Morning Call". After seeing Jefferies listed at or near the top once a week for a couple years, it was unbelievable to see him join the Phils.
For me it was the Dodgers of 74 acquiring the toy cannon Jimmy Wynn. The fans took to him and he had a great year although I don't have the stats to back that up. Doesn't come close to the Lakers acquiring Kareem from Milwaukee shortly after that but that is for another board.
I would like to suggest the Indians' signing of Wayne Garland to a 10-year deal worth (gasp!) $1.3 million. In today's money it might have been worth it. He did have one decent season.