Our best-ever MLB winter meetings trades, rumors and untold tales from the lobby


In a normal year, baseball’s winter meetings are a gathering of team executives of all stripes, player agents and journalists where the hot stove starts gaining steam and the trade and free-agent markets start buzzing. This, of course, is not a normal year.

Instead of crowding into the lobby of the Omni Dallas Hotel and the Kay Bailey Hutchison Convention Center, where the 2020 winter meetings were scheduled to be held this week, the gatherings will be held virtually. That leaves our collection of baseball reporters to recall winter meetings past, including their favorite blockbuster deals and rumors, moments they’ll never forget, what they’ll miss (and what they won’t) with the meetings being held through computer screens and their favorite untold tales from the lobby.

What one move is the biggest winter meetings move ever?

Tim Kurkjian: The biggest trade I ever covered at the winter meetings came on Dec. 5, 1990, at the meetings outside of Chicago. The Toronto Blue Jays sent first baseman Fred McGriff and shortstop Tony Fernandez to the San Diego Padres for second baseman Roberto Alomar and outfielder Joe Carter. McGriff had hit 105 home runs in his previous three seasons combined; someday he might be a Hall of Famer. Fernandez had made the All-Star team in three of his previous four seasons, an excellent player in his prime. Carter had averaged nearly 30 homers a year for the previous four seasons; he, of course, hit the walk-off home run to win the 1993 World Series for the Blue Jays. Alomar was the best player on two World Series championship teams (1992 and 1993) in Toronto and would be a first-ballot Hall of Famer. The day of the trade, some in the media called it the Fred McGriff trade, the Joe Carter trade, the Tony Fernandez trade. Blue Jays general manager Pat Gillick whispered to me late that night, “This will always be known as the Roberto Alomar trade.”

Jeff Passan: As partial as I am to the Carter/Alomar/McGriff/Fernandez blockbuster trade in 1990, the only answer is the Texas Rangers signing Alex Rodriguez to a 10-year, $252 million deal at the 2000 meetings in Dallas. It’s the single most consequential contract in sports history.

Joon Lee: Recency bias! The Chris Sale trade in 2016 from the Chicago White Sox to the Boston Red Sox is a move that had ramifications for the Red Sox franchise beyond the team’s World Series title in 2018. Dave Dombrowski’s decision to sign Sale to a massive extension (paired with the four-year, $68 million contact given to Nathan Eovaldi) eventually put the franchise in a financial position where it felt the need to trade Mookie Betts and David Price to the Los Angeles Dodgers, which obviously played a big role in crowning the most recent World Series champion.

David Schoenfield: Instead of a trade, I’m going with two landmark free-agent signings: Dave Winfield’s 10-year, $23 million contract with the New York Yankees at the 1980 meetings and Kevin Brown’s seven-year, $105 million deal with the Los Angeles Dodgers in 1998. Both deals rocked the sport and led to the inevitable cries that baseball was broken. Both were star players, but not necessarily the best in the game, and Brown was 34 years old. Just a year before Winfield’s contract, Nolan Ryan had become the sport’s first million dollar-a-year man, signing a four-year, $4.5 million contract with the Houston Astros. Yankees owner George Steinbrenner blew that away. Eighteen years later, Brown crossed baseball’s version of the 4-minute mile with the first $100 million deal (skipping past $14 million in annual salary to reach $15 million). The deal enraged front offices around the game. “There is no appropriate comment,” commissioner Bud Selig said. Brown lasted five seasons with the Dodgers — and they never made the playoffs.

Bradford Doolittle: The San Francisco Giants‘ signing of Barry Bonds during the 1992 winter meetings was seismic. It’s not every day a franchise acquires a best-in-the-game player in the prime of his career. Love Bonds or hate Bonds, it was a watershed move in baseball annals.

Alden Gonzalez: I don’t know if this is actually it, but I’ll go with the Los Angeles Angels signing Albert Pujols in 2011 at least partly because of where I was at the time — in my early 20s and a month into my first beat, covering, of course, the busiest team of all. The final day of the winter meetings is typically uneventful; the Rule 5 draft takes place in a giant conference room early in the day, then all the executives and reporters rush out of the hotel to catch their flights back home. But it started to feel as if this year’s version would be completely different the night before, when word began to spread that the Angels — with two legitimate first basemen already on their roster — were serious about signing a man who at that point was still the game’s greatest player. The following morning, just before those conference-room doors opened to the media, the Angels landed Pujols with a historic contract. Within the hour, C.J. Wilson agreed as well. On one of the industry’s most tedious days, the Angels spent more than $300 million. I might have blacked out.

Jesse Rogers: In 1999, Johan Santana was a Rule 5 pick by the Marlins from the Astros, and then was dealt to the Minnesota Twins in a prearranged deal. Santana is regarded as the second-best Rule 5 pickup ever. (The Rule 5 draft wasn’t done at the winter meetings when the Pirates selected Roberto Clemente from the Dodgers.) Getting a player of that caliber without giving up inventory is an executive’s dream.

Which team, in which year, made the all-time biggest winter meetings splash — and how did it end up working out?

Schoenfield: Let’s look at what Whitey Herzog did for the St. Louis Cardinals at the 1980 winter meetings. The Cardinals had been stuck in neutral for more than a decade and finished 74-88 in 1980. Hired as the club’s GM in August, Herzog made himself the manager as well, then set out to remake the club. He signed Darrell Porter as a free agent, then made three big trades involving 23 players, trading away 12. He acquired two future Hall of Fame relievers (Bruce Sutter, Rollie Fingers) and then traded away Fingers and another Hall of Famer, Ted Simmons. The deals involved four All-Star catchers (Porter, Simmons, Gene Tenace, Terry Kennedy). He traded away a future Cy Young winner (Pete Vuckovich). In all, 11 of the 23 players accumulated at least 10 career WAR and most were still in their primes or early in their careers at the time. And that wasn’t all. The following offseason, Herzog used two of the players acquired in 1980 (Sixto Lezcano and Lary Sorensen) to help acquire Ozzie Smith and Lonnie Smith. The Cardinals had the best record in the NL East in 1981 and won the World Series in 1982 — and basically have been good ever since.

Kurkjian: The biggest splash at the winter meetings was made in 2000 in Dallas by the hometown Rangers, with owner Tom Hicks leading the way. The Rangers signed free-agent shortstop Alex Rodriguez to a record contract worth $240 million, twice as much as any team had offered. It was a stunning amount of money back then. Rodriguez’s agent, Scott Boras, set up in the hotel lobby, and explained every line of the contract to all who wanted to listen. Rodriguez had three brilliant years in Texas, with a combined OPS of 1.030. He finished sixth, second and first in the MVP balloting. He won two Gold Gloves. But the day of the deal, a member of the Rangers told me, “He’s great, but this was a bad signing. We don’t have any money left for anyone else.” Indeed. The Rangers went 216-270 in Rodriguez’s three years, finishing in fourth place each year in the American League West, a combined total of 99 games out of first place. On the final day of the meetings, an ice storm of biblical proportions clobbered the Dallas-Fort Worth Metroplex. Was it a sign of things to come?

Doolittle: I go back to one of the most epic deals in winter meetings history, when the Blue Jays sent McGriff and Fernandez to San Diego for Carter and Alomar. Toronto won back-to-back World Series in 1992 and 1993, with Alomar serving as a catalyst and Carter providing a historic World Series-ending homer in 1993.

Gonzalez: Relative to their revenue streams, I’ll go with the Miami Marlins in 2011. They were heading into a new, taxpayer-funded stadium, ownership promised to spend on the rosters, and so Jeffrey Loria, David Samson and Michael Hill patrolled the Hilton Anatole Hotel in Dallas like wannabe mobsters, negotiating with the agents of all the biggest free agents and at times pressuring them into quick decisions. They ultimately signed Jose Reyes, Mark Buehrle and Heath Bell over a five-day stretch — and it went about as poorly as you could imagine. Seven months later, the Marlins traded away most of their good players and went into another full-scale rebuild.

Rogers: It doesn’t sound like a big deal now, but when the Yankees inked Winfield to that 10-year contract in 1980, it shocked the sports world. The concept of free agency was still in its infancy and players simply weren’t getting mammoth deals back then — though it was worth only $23 million. Winfield was fine for them, but the Yankees didn’t win anything during his tenure in New York.

Passan: White Sox owner Bill Veeck literally unveiled an “Open For Business” sign at the 1975 meetings in Fort Lauderdale, Florida, and proceeded to make six trades. It did not work out well. Chicago went 64-97.

What is your personal favorite winter meetings move?

Lee: The series of small transactions the Red Sox made at the 2012 winter meetings, signing Shane Victorino and Mike Napoli, didn’t make major headlines or set any contract records, but proved that the most important signings don’t need to be with the highest-profile players. Victorino (.801 OPS, 15 homers, 26 doubles) and Napoli (.842, 23 homers, 38 doubles) provided depth to the Red Sox’s roster and played critical roles in Boston’s 2013 World Series run.

Kurkjian: My favorite trade of the winter meetings occurred on Dec. 4, 1988. The Orioles, the team I covered for The Baltimore Sun, sent star first baseman Eddie Murray to the Dodgers for pitchers Jay Howell and Brian Holton, and shortstop Juan Bell. Murray would be a first-ballot Hall of Famer just from his 12 years in Baltimore. It was an enormous deal for both teams, but it had been kept so secretive until we discovered that Roland Hemond, the GM of the Orioles, and Fred Claire of the Dodgers, had met in a hotel in Chicago shortly before the meetings to discuss the deal. When I called Hemond in his hotel room, he said, “You ask tough questions,” and answered none of them. Hemond is an all-time favorite; he did everything honestly, by the book. So when I walked with him on his way to the podium to officially announce the Murray trade, I asked for the third player the Orioles were getting. Hemond said, “Sorry, I can’t tell you until the deal is done.” Ten seconds later, he announced the trade.

Schoenfield: The four-team trade in 1977 involving the Rangers, Pirates, Mets and Braves, involving 11 players. Hall of Famer Bert Blyleven was the best player, going from the Rangers to the Pirates. The Rangers acquired outfielder Al Oliver, a three-time All-Star at the time, from the Pirates, and Jon Matlack, one of the best lefties in the game, from the Mets. The Braves acquired prospects from the Rangers and sent first baseman Willie Montanez, an All-Star in 1977, to the Mets. The big winner? Pittsburgh, as Blyleven would help the Pirates win the 1979 World Series. We definitely need more four-team trades! (Make it happen, Jerry Dipoto.)

Gonzalez: When the Cubs signed Jon Lester in 2015, largely because of what it meant — that the “Lovable Losers” were suddenly a force. The Cubs were a last-place team in 2014, but Joe Maddon had arrived, Kris Bryant was on his way and Jake Arrieta had emerged. There was a sense heading into those meetings that the Cubs might do something significant. Then they signed Lester to a whopping six-year, $155 million contract — topping the Boston Red Sox, San Francisco Giants and Los Angeles Dodgers for his services — and proved they were serious. Word spread through downtown San Diego late on a Tuesday night. I was returning from dinner in the Gaslamp Quarter. And walking directly in front of me was Maddon, who was on his way to see Theo Epstein. He was, as you might expect, beaming.

Passan: Eminent Washington Post baseball writer Dave Sheinin ordering Hattie B’s hot chicken to be delivered to the Gaylord Opryland hotel — and saving me from passing out due to low blood sugar.

What is one rumor — that never came to be — that rocked a winter meetings?

Kurkjian: My favorite rumor at the winter meetings wasn’t a rumor for long, and, like so many rumors, turned out to be nothing. Phillies GM Paul Owens, “The Pope,” as he was known, was a character. Famously, after several drinks at 1:30 a.m. at one winter meetings, Owens, dressed in a coat and tie, demonstrated the proper way to execute a hook slide on the floor of the lobby bar. At the 1979 winter meetings, Owens called the Phillies beat writers at 2:30 a.m. to tell them that he had just acquired Sutter. The writers, at least for a minute, thought he meant Bruce Sutter, the star closer for the Cubs. Owens laughed mightily, then told the writers that the Phillies had acquired a minor leaguer, pitcher Burke Suter.

Passan: The Marlins being players in the Albert Pujols derby in 2011. Lest you think they dodged a bullet, the Marlins wound up instead committing $191 million to Jose Reyes, Mark Buehrle and Heath Bell.

Doolittle: Alas, my winter meetings history is recent, which means the totality of my experience is waiting around for something to happen and then nothing ever does. Even the rumors have been dull the past few years.

What is the most bonkers quote you’ve ever heard at the winter meetings?

Rogers: The speaker of the quote is easy; picking just one from Scott Boras is another story. There are many, but how about this one, regarding the Yankees being slow to make moves one offseason: “When the nurse comes into your room with a thermometer, the issue isn’t the temperature of the patient that day. It’s their health when they’re ready to leave the hospital. And they’re not ready to leave the hospital.”

Kurkjian: My favorite quote from any winter meetings came in 1982. The lowly Rangers, the team I covered for The Dallas Morning News, had gone to the meetings with big hopes of making several major trades or signings, all of them necessary. Instead, all they came home with was reliever Odell Jones in the Rule 5 draft. I asked how the team was going to explain the disappointing meetings to its fans. Assistant GM Paul Richards, a venerable baseball man, said, “Well, we’re going to have to sell the s— out of Odell Jones.”

Passan: “I’m going to burn your f—ing house down.” — One unidentified agent to another during a parking-lot fracas at the 2013 meetings. The involved parties remain unknown.

What will you miss most/least about the meetings now that they’ve gone virtual for 2020?

Kurkjian: What I will miss the most — and the least — about the winter meetings are the millions of trips through the lobby. There is so much to love there, so much to learn and so much misinformation to fear. The lobby has changed dramatically over the years. Now, it’s hard to find GMs in the lobby; they’re locked in their private suites with their armies of assistants, none of whom can complete a hook slide in the lobby bar at 1:30 a.m.

But one thing never changes: the number of rumors you hear, some of them ridiculous. A few years ago at the winter meetings, my duty one day was to walk through the lobby and report back with the most outrageous rumor I heard. One team executive, not a GM, much lower on the chain, cupped his mouth like a pitcher talking to his catcher in a mound meeting, then warned me about an available free agent.

“I heard,” the executive said, “that he killed someone.”

I won’t miss that.

Lee: The fact that the entire baseball world congregates in a hotel lobby and you have an opportunity to catch up with sources and friends from around the industry whom you see only a handful of times a year, often at the big baseball events like the All-Star Game or the World Series. It’s a great annual reminder that the world is a lot smaller than it can sometimes seem.

Passan: I will miss the 3 a.m. drinks in hotel suites where I hear a funny story or get a great tip. I will not miss the alarm going off at 6:30 a.m.

Doolittle: The only real highlights to the meetings I’ve been to the last couple of years is the announcement of the Hall of Fame Era committee selections that have taken place the first night of the meetings. Agree with the picks or not, these are mostly players who were overlooked while on the BBWAA ballot and it’s always moving to see them glory in the knowledge that they are bound for Cooperstown. I won’t miss standing around hotel lobbies. At all.

Rogers: Reconnecting with executives and agents you don’t see during the year but only talk to will definitely be missed. Running through enormous hotels to track people down won’t.

Gonzalez: What I’ll miss the least is the overall concept; it got to a point when executives hardly ever appeared in the lobby, which at times made it seem rather pointless to report on site. And so what you had was a ton of loitering media members, a few of them scrounging for any morsel of information — much of it, because of the circumstances, either inconsequential, misleading or incomplete — and a few others merely pretending to work. What I’ll miss most is the nights — gathering with reporter friends over dinner, everyone anxious over the threat of major news interrupting everything, then congregating at the hotel bar and not knowing which executive or coach or agent or even player might be there. That’s when the real reporting happened.

What is your best previously untold tale from the winter meetings lobby (or bar, or elsewhere)?

Passan: At the 2015 meetings, my colleague at the time, Tim Brown, got a tip: Cincinnati closer Aroldis Chapman, who was on the verge of being traded by the Reds, had gotten into trouble off the field. He didn’t have any firm details.

So we started hunting around and found what we thought might be a promising lead: police reports in the area near where Chapman lived. One problem: They needed to be picked up in person. And, well, Nashville isn’t exactly driving distance to Miami.

Thankfully, my friend Max is a schoolteacher in South Florida, and he said he’d be happy to hustle over to the police department and request the documents. A few hours and 17 cellphone pics later, we had the full file — and a story about Chapman allegedly firing a gun indoors that scuttled the Reds’ trade with the Los Angeles Dodgers, which wound up landing him with the Yankees, and eventually led to the first suspension under MLB’s new domestic violence policy.

Doolittle: This is personal and speaks to the fact that I’m a walking bag of personality disorders. You’ve heard the term “fanboy,” right? Whatever the opposite of that term is, that’s me. If I encounter someone whom I don’t know but hold in high esteem, I cannot bring myself to acknowledge that person, no matter what he or she has meant to me as a person, a writer, a baseball journalist, whatever. I have never once in my life asked a person for an autograph. I’m not proud of this.

Well, in Orlando a couple of years ago, I found myself in line to get food behind Bill James. I’m not unlike many baseball writers and wanna-be analysts — James has had and continues to have a profound impact on the way I think about the game. We also happen to have both been raised in the rural Midwest. I was introduced to him once years ago at a SABR event in Kansas City, but it was awkward and fleeting, so I knew he didn’t recognize me. I followed him through the food line, which had to take at least 10 minutes. I encountered him again waiting for the elevator, then rode up the elevator with him for a few floors, just the two of us. I may have nodded at him at some point, but no words were exchanged.

Rogers: The Cubs’ signing of Lester in 2015 was on the verge of falling apart at times before it finally came together. Both sides were unsure if the other was being completely honest about leaks, but when the deal came to pass, all were thrilled. But it came close to not happening. Afterward, the Cubs’ party began in their suite and moved down to the hotel bar for a long night of celebrating.



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