Friday, October 23, 2026

October 23, 1996: The Jim Leyritz Game II

October 23, 1996, 30 years ago: Game 4 of the World Series, at Atlanta-Fulton County Stadium. The Atlanta Braves rock New York Yankees starter Kenny Rogers, and lead 6-0. The Yankees close to within 6-3, but in the top of the 8th, they are 4 outs away from being down 3 games to 1 in the Series, their great season coming to a very disappointing close.

But they get 2 runners on, and backup catcher Jim Leyritz comes to bat against Braves closer Mark Wohlers. After throwing 98- and 99-mile-per-hour fastballs that Leyritz can only foul off, Wohlers hangs an 86-mile-per-hour slider. Leyritz, a postseason hero for the Yankees a year earlier with his 15th-inning walkoff homer in the Division Series against Seattle, knocks it over the left-field fence to tie the game.

The Yankees load the bases in the 10th, and Hall of Fame 3rd baseman Wade Boggs, whom Torre had benched in favor of Charlie Hayes due to his usual magnificent hitting having failed him, is sent up to pinch-hit. Boggs draws one of the most important walks in baseball history, and it's 7-6 Yanks. An error makes the final score 8-6 Yanks.

Not since the 1929 Cubs, going from 8-0 up to 10-8 down in the 7th inning of Game 4, had a team blown a lead of 6 or more runs in a World Series game. The Yankees were in serious trouble, but now the Series is tied, and anything can happen. In this 1996 season, lots of "anythings" have already happened for the Yankees.

The next night, Game 5 was, regardless of result, the last event at Fulton County Stadium, as the Braves were moving into the next-door Turner Field the next season, and the NFL's Falcons had moved into the Georgia Dome after the 1991 season. The Yankees won, 1-0. Two nights later, they won Game 6 at Yankee Stadium, 3-2, completing their remarkable comeback, and winning their 23rd World Series.

The Yankees traded Leyritz in 1997. He helped the San Diego Padres reach the World Series in 1998 -- against the Yankees. In 1999, the Yankees reacquired him, and he helped them with another World Series, hitting what turned out to be the last home run of the 20th Century in Game 4. This led NBC's Bob Costas to say, "You could send this guy to a resort in the spring and summer, as long as he comes back for October." His career ended in 2000 with the Los Angeles Dodgers.

Leyritz has had his ups and downs since. In 2006, he admitted that he'd used amphetamines while playing -- legal at the time, and not nearly as performance-enhancing as steroids. (So if you want to invalidate the Yankees' 1996 and 1999 World Championships because of this, you shouldn't.) In 2007, he killed another driver in a drunken crash. He ended up serving 10 days in jail and a year's probation. In 2009, he was charged with domestic violence for hitting his wife, although she later dropped the charges (but also dropped him through divorce -- they had 4 children).

In 2011, he was a coach for the Newark Bears of the Atlantic League. In 2012, he worked for the Yankee front office. He lives in the Orange County suburbs of Los Angeles, with his new wife, Michelle, his 3 kids and her 2. He co-hosts a radio show in Los Angeles for SB Nation Radio.

Thursday, October 22, 2026

October 22, 2001: 116 Wins and No Pennant

October 22, 2001, 25 years ago: Bernie Williams, Paul O'Neill and Tino Martinez hit home runs, backing the pitching of Andy Pettitte, and the New York Yankees win Game 5 of the American League Championship Series, 12-3 over the Seattle Mariners at Yankee Stadium, and take their 38th Pennant.

The Mariners had beaten the Yankees in the 1995 AL Division Series, before losing the ALCS to the Cleveland Indians. Still, it helped to save Major League Baseball in the Pacific Northwest, by convincing people to vote to approve a new ballpark. Safeco Field (now named T-Mobile Park) opened in 1999. In 2000, the M's got back to the ALCS, but, this time, the Yankees beat them.

In 2001, the M's got off to a 20-4 start, and were 9 games ahead of the rest of the AL Western Division. By May 17, they were 31-9, and 12 games up; by June 16, 52-14, and 20 games up. Their fans were going into Internet chat rooms with screen names like "Seattle Mariners 2001 World Champions."

The All-Star Game was set for Seattle that year, on July 10. The Mariners were 63-24, leading the Division by 19 games, and had 8 players selected for the game: Pitchers Freddy Garcia, Jeff Nelson and Kazuhiro Sasaki; designated hitter Edgar Martinez, 1st baseman John Olerud, 2nd baseman Bret Boone, center fielder Mike Cameron, and, in right field, Ichiro Suzuki.
With his first name, and former Mariner ace Randy Johnson's number on his back, "ICHIRO" and 51, he had a cannon of a right arm, and would finish the season leading the AL in batting at .350, hits with 242, and stolen bases with 56.

Though he had played in Japan's Pacific League for 9 seasons, and the game in question was played on his 28th birthday, he was named the AL's Rookie of the Year, and became only the 2nd player, after Fred Lynn in 1975, to win either League's Rookie of the Year and its Most Valuable Player awards in the same season.

On August 5, 2001, the Cleveland Indians accomplished a historic 12-run comeback, defeating the Mariners 15-14 in 11 innings, after trailing 14-2 in the 7th inning. This remarkable victory, known as the "Great Return," tied a major league record for the largest comeback in a game, featuring five runs with two outs in the ninth inning.

But Mariner fans shook it off. The team won its 100th game on September 5, over the Tampa Bay Devil Rays, having lost only 40. When MLB paused after the terrorist attacks on September 11, the Mariners were 104-40, and in the 5th game of what turned into a 7-game winning streak. They clinched the Division on September 19, 5-0 over the team then known as the Anaheim Angels, with Jamie Moyer pitching a shutout.

On October 5, they beat the Texas Rangers at home, 6-2, to win their 115th game of the season, breaking the AL record set by the Yankees in 1998. On October 6, they won their 116th, beating the Rangers, 1-0, on a shutout by Joel Piñeiro, tying the major league record set by the 1906 Chicago Cubs.

They could have set a record with a 117th win the next day, but lost to the Rangers, 4-3. Like the August 5 loss to Cleveland, it didn't seem like a sign at the time. M's fans went into the ALDS, also against Cleveland, full of confidence that this would be the year for their 1st-ever Pennant and World Championship.

But the Indians won Game 1 in Seattle, 5-0. The Mariners bounced back in Game 2, 5-1. Then, the Indians won Game 3 in Cleveland, 17-2, one of the biggest blowouts in postseason history. The Mariners won Game 6-2, to send it back to Seattle, where they won Game 5, 3-1. This was the first time all season that they had really been tested. Maybe it would help them.

But the Yankees had been tested time and time again, including coming from 2-0 down at home to take 3 straight ALDS games from the Oakland Athletics. And, having beating the M's in the ALCS the season before, they weren't going to be intimidated by 119 wins (counting the ALDS). After all, in 1998, counting the postseason, they'd won 125, and a lot of those '98 Yankees were still there in 2001.

Again, the home teams fell short in this series. The Yankees stunned the Northwesterners by winning 4-2 and 3-2 in Seattle. But in Game 3 in The Bronx, the Mariners won, 14-3. Game 4 was scoreless through 7 innings, but each team scored a run in the 8th. With 1 out in the bottom of the 9th, closer Sasaki gave up an infield single to Scott Brosius, and Alfonso Soriano then hit a game-winning home run, 3-1 New York.

After the game, the Mariners' manager made a bold statement to the media: "We're going home for Game 6." He was, essentially, making a guarantee. He was tempting the ghosts of Yankee Stadium. He should have known better, because he was one of them: His name was Lou Piniella, and he had played on the Yankees' 1976-81 dynasty.

Game 5 was put away early. The Yankees scored 4 runs in the 3rd inning, with 2 coming on a Bernie Williams home run. Paul O'Neill added a solo homer in the 4th. The Yankees tacked on 4 more runs in the 6th, and it was 9-0.

Yankee Fans chanted, "One sixteen!" "O-ver-RA-ted!" and, for Ichiro -- I'm sure most of them didn't realize it was his birthday -- "SAY-o-NA-ra!" (Japanese for "Goodbye.")

Ichiro went on to collect 3,089 hits in the North American major leagues. This included 2,030 in the 2000-09 decade, to lead all players. And that included 262 in 2004, a new single-season record.

The Mariners did score 3 in the top of the 7th, but the Yankees came back with 3 in the bottom of the 8th, and won, 12-3. For the Yankees, it was their 5th Pennant in the last 6 years, and a tremendous lift for the City of New York after the events of last month.

For the Mariners, it was a crushing defeat. They had tied an all-time major league record with 116 wins, but had totally flopped against the Yankees. They did reach the postseason again for 21 years. With the Washington Nationals winning one in 2019, the Mariners became the only active team in Major League Baseball never to have won a Pennant. The last Seattle-based team to win a Pennant was the Seattle Angels, in the Class AAA Pacific Coast League, in 1966.

October 22, 2001: "Pardon the Interruption" Premieres

Tony Kornheiser (left) and Michael Wilbon

October 22, 2001, 25 years ago: ESPN premieres its show Pardon the Interruption. Just as I would later describe Around the Horn, which debuted on the network a year later, as "The McLaughlin Group for sports," PIT is to sports what Crossfire was to politics.

Tony Kornheiser, from Lynbrook, Long Island, New York, was 53 years old when the show began, although his advancing age would become a running gag. Michael Wilbon, from the South Side of Chicago, was about to turn 43, although, as the show went on and he became, in his own words, "an old man," he seemed to enjoy telling younger athletes and fans, "Get off my lawn!"

Both were sportswriters at The Washington Post, Kornheiser from 1979 to 2008, Wilbon from 1980 to 2010, both eventually becoming regular columnists before getting bought out. Kornheiser grew up as a fan of the New York Mets, Jets, Knicks and Rangers; Wilbon, of the Chicago Cubs (despite growing up in White Sox territory), Bears, Bulls and Blackhawks. But both retain affection for the D.C.-area teams, including the teams of the University of Maryland and Georgetown University, due to having covered them for the Post.

The show begins with "Headlines": They discuss three major sports stories of the day. Each segment has a clock, usually no more than 2 minutes. After a commercial break, they might do more Headlines. Or they might do a short in-depth interview with another ESPN expert on a particular sport, calling the segment "Five Good Minutes."

Or they might play a game. Sometimes it's "Toss-Up," where they choose between two preferences: Who's likelier to win a game, who's the better performer at a particular event, which coach is on a hotter "hot seat," etc. Sometimes, it's "What's the Word?" where they choose a word to describe an occurrence in sports. Sometimes, it's "Mail Time," where they read questions sent in by viewers, and answer them.

Long-since discarded games were:

* "Odds Makers," in which their former assistant, Tony Reali -- known as "Stat Boy," before (and, for a few more years, after) becoming host/moderator of Around the Horn -- would ask what were the odds of something happening.

* "Over/Under," in which Reali would give them a number of something, like how many games a team would win, and they had to guess over it or under it.

* "Role Play," where they would hold up a picture of an athlete or coach, and the other man would ask him a question, and he had to answer it in his perception of that person's character.

* "Good Cop, Bad Cop," in which one would be nice about an issue and the other would be mean.

* "Food Chain," where they would rank certain items, leading to Tony creating a catchphrase that has survived the segment: "That's it, that's the list!"

Then, another commercial break. Then, "Happy Time." First, they wish a sports figure a Happy Birthday, and talk about them for about 30 seconds. If it's an old guy, Tony will said, "History lesson, kids!" Then, "Happy Anniversary" -- or, sometimes, "Not-So-Happy Anniversary." Finally, "Happy Trails" to a coach getting fired, a player retiring, a streak ending, or a seemingly likely event failing to happen. If a sports figure has died, "Happy Trails" is replaced by "A Melancholy Trails" and a considerably more respectful discussion.

By this point, the clock will show under 2 minutes left to do the show. This is followed by "Errors and Omissions." Finally, the Big Finish: Tony will say, "We're running out of show! It's time for the big finish!" and Mike will say, "Let's do it!" Five brief segments, Tony introducing the 1st, 3rd and 5th, Mike the 2nd and 4th.

After Mike responds to the last, Tony says, "We're out of time. We'll try to do better the next time. I'm Tony Kornheiser!" And Mike says, "And I'm Mike Wilbon. Same time tomorrow, knuckleheads!" Unless it's a Friday, in which case, it's "Have a great weekend, knuckleheads!" Or, if they're pre-empted, "We're bumped by basketball/golf/tennis 'til (whatever the day is), knuckleheads!" Followed by Mike introducing the show at 6:00: "Here's SportsCenter!" Or, if it's Monday night, "Here's Monday Night Countdown!"

Frequent references are made to their colleges: Tony's Binghamton University in New York State, and Mike's Northwestern University north of Chicago. Mike refers to Tony's bias toward New York, or at least to the Northeast, referring to the main Interstate highway, I-95, as opposed to his own Midwest, or "Big Ten" or I-94 region.

Less frequent than usual are Wilbon's references to guys Tony likes as "Your boy!" Tony began to fire back when Wilbon waxed about Chicago-adjacent personalities, and called them "Your boy!"

They dress up for Halloween, and, on their last show before Thanksgiving Day, they do "The Turkeys of the Year." Tony says, "Wilbon, tell them the rules" (for deciding them). Mike says, "There ain't none." And then they show bloopers, and athletes, coaches and owners who made fools (or "turkeys") of themselves in various ways.

When the show was suggested to them, because they had such great chemistry together when talking about sports, both of them thought the show, airing weekdays at 5:30 PM Eastern Time on ESPN and repeated at least once a day on ESPN2, would last a few weeks at most. Nobody is more surprised than they are that, as of October 22, 2026, it is still on the air, and that they're still the ones doing it.

But they don't always do it in the D.C. studio where it is taped, usually broadcast live. Wilbon frequently does it from the arenas where he covers NBA games for the network. Sometimes, he's back home in Chicago, doing it from ESPN's studio there. Sometimes, he's at ESPN's studio in Phoenix, because he has a house in suburban Scottsdale, Arizona -- Phoenix being to Chicagoans what Florida is to New Yorkers: Where you go to retire. Except Wilbon has no intention of retiring.

Likewise, when COVID hit in March 2020, Tony started doing the show from his house in the Chevy Chase section of Northwest Washington (which borders the city of Chevy Chase, Maryland). Even after restrictions were lifted, the joke is that he does the show from his attic. It took about 2 years for him to once again do the show from his studio -- and on the day that he did it, Wilbon was on assignment, covering a Lakers-Warriors game in Los Angeles!

Occasionally, one or both will be out -- the joke is that Tony is tired, or that either one of them is indulging in their golf fetish -- and replaced by a substitute. For years, a regular sub was Dan LeBatard of the Miami Herald, and both Tony and Mike pretended that they hated him. Sometimes, it's Frank Isola of the New York Daily News, a.k.a. "Fill-In Frank." Sometimes, it's another ESPN correspondent, such as Pablo Torre (whom Tony jokes is "my son") or Mina Kimes.

In 2004, CBS tried to build a sitcom around Tony, titled Listen Up. It starred Jason Alexander of Seinfeld as Philadelphia-based sportswriter Tony Kleinman, who hosted a talk show titled Listen Up with Bernie Widmer, a former NFL player played by Malcolm-Jamal Warner of The Cosby Show. Like Home Improvement, it tried to balance the protagonist's work life with the TV show and his home life with his wife and kids in the suburbs. Unlike the show on which it was based, it didn't work, and was canceled after 1 season, 22 episodes.

October 22, 1926: The Tragedy of Harry Greb

October 22, 1926: Harry Greb, a former Middleweight Champion of the World, dies in Atlantic City, New Jersey. He was only 32 years old.

Edward Henry Greb was born on June 6, 1894 in Pittsburgh, leading to his nicknames: "The Pittsburgh Windmill," "The Smoke City Wildcat" and "The Pittsburgh Bearcat." I thought his surname might have been shortened (either by him or his father) from a longer one, either Slavic or Italian, but, apparently, that was it, and he was of German descent.

By 1915, he was fighting world-class opposition, including 2 fights, though not sanctioned for the title, against Middleweight Champion George Chip. He lost both fights by what was then called a "newspaper decision." In 1917, he set a record that will almost certainly never be broken with 37 officially sanctioned fights in a single year -- an average of 1 every 9.8 days. He won 34 of them. He beat Barney "Battling" Levinsky, the Light Heavyweight Champion, although, again, the title was not officially on the line. Starting in 1918, he won 52 straight fights, including fights against Levinsky, and Billy Miske and Mike Gibbons, both of whom would later fight Jack Dempsey for the Heavyweight Championship.

In 1921, during a fight with light heavyweight Kid Norfolk, he was thumbed in the right eye, which is believed to have resulted in a retinal tear. He would eventually lose all sight in the eye, and lose some vision in his left eye as well. He kept this a secret from everybody except his wife and his closest friends. If even one State boxing commission found out, it would have notified the commissions in the other 47 States then in the Union, and Greb wouldn't have been able to box anywhere in America.

Despite the injury, Greb won the fight via a newspaper decision, and got a fight for the American light heavyweight title. On May 23, 1922, he faced champion Gene Tunney at the 2nd Madison Square Garden. In the 1st round, Greb broken Tunney's nose. Somehow, Tunney, a wealthy and cultured man who had learned to box while serving in the Marine Corps during World War I, managed to avoid getting knocked down, let alone out. Greb was announced as the winner, and The Ring magazine named it Fight of the Year.

It was the only professional fight Tunney ever lost. They fought at the 2nd Garden again on February 23, 1923, and Tunney won by a split decision. They fought there a 3rd time on December 10, 1923, and Tunney won by a unanimous decision. They fought a 4th time, on September 17, 1924 at the Olympic Arena in Cleveland, and it was ruled a draw. They fought a 5th time on March 27, 1925 at the St. Paul Auditorium in Minnesota, and Tunney won another unanimous decision.

A boxer facing a man 5 times? Greb fought Levinsky 6 times, and won them all. He also faced former Light Heavyweight Champion Tommy Loughran 6 times, losing the 4th, drawing the 6th, and winning the rest.

On August 31, 1923, Greb finally got his shot at a World Championship, winning a unanimous decision over Middleweight Champion Johnny Wilson at the Polo Grounds. He successfully defended the title 5 times, including a rematch against Wilson at The Garden in 1924; and one over then-Welterweight, later Middleweight, Champion Mickey Walker, "The Toy Bulldog," at the Polo Grounds in 1925.

On February 26, 1926, 2 months after the 3rd Madison Square Garden, the building that would become known as "The Old Garden," opened, he lost the title in a split decision to Theodore "Tiger" Flowers, who thus became the 1st black fighter to win the Middleweight title. After winning 2 tuneup fights, Greb fought a rematch, but Flowers won on an even more controversial split decision. This time, the fans stormed the ring to protest the outcome. Greb later stated, "Well, that was one fight I won, if I ever won any."

Officially, he won 108, lost 8, and drew 3. Of those 8 losses, 3 were to Tunney and 2 were to Flowers. Of those 108 wins, 33 of them were over 16 different members of the International Boxing Hall of Fame, and Greb is still the all-time leader in that category.

But he had to retire. His health, as had his face, had taken a beating. Not only did he have to have his right eye removed and replaced with a glass prosthesis, but damage to his nose had led to breathing issues. It forced him to turn down a job as a sparring partner for Dempsey, who was about to defend the Heavyweight Championship against Tunney in Philadelphia. Knowing both men's styles well, Greb was sure that Tunney would win that fight. He was right, and Tunney won the rematch as well, which became known as the "Long Count Fight."

Greb saw the 1st Dempsey-Tunney fight, but not the 2nd. He checked into a hospital in Atlantic City for surgery, but complications set in, causing a heart attack that killed him on October 22, 1926. He has been called the greatest middleweight fighter of all time, and one of the very greatest boxers, pound-for-pound, who has ever lived. But the thing that stands out the most about him isn't his fight totals, or his holding of a championship for 3 years, but the fact that he was the only man ever to beat Tunney, who remains the only man ever to retire while still Heavyweight Champion and stay retired.

October 22, 1926: "The Sun Also Rises" Is Published

October 22, 1926, 100 years ago: The Sun Also Rises, written by Ernest Hemingway, is published by Charles Scribner's Sons. Although Hemingway had previously been a journalist, and had published short stories, this was his 1st novel, and it set the tone for a writing style that would change literature.

The novel is a roman à clef: The characters are based on real people in Hemingway's social circle, and the action is based on real events, particularly Hemingway's life in Paris in the 1920s, and a trip to Spain in 1925 for the "running of the bulls" festival in Pamplona and fishing in the Pyrenees.

Hemingway, then 27 years old, presented his notion that what was already being called the "Lost Generation," considered to have been decadent, dissolute, and irretrievably damaged by their experiences in World War I, which had ended just 8 years earlier, was, instead, resilient and strong. Hemingway investigated the themes of love and death, the revivifying power of nature, and the concept of masculinity.

However, in his treatment of women, art imitated life: The character of Lady Brett Ashley is promiscuous and untrustworthy. Hemingway married 4 times, and it's been suggested that he mistreated all 4 wives, but got a great novel out of each: The Sun Also Rises, A Farewell to Arms (a version of his experience in World War I, published in 1929), For Whom the Bell Tolls (a version of his experience in the Spanish Civil War, published in 1940), and The Old Man and the Sea (based on stories he heard from fishermen in Cuba, published in 1952).

Along with The Great Gatsby by his friend F. Scott Fitzgerald, and Main Street by Sinclair Lewis, The Sun Also Rises is 1 of 3 definitive novels of the "Roaring Twenties" and the "Lost Generation." But it has not really stood the test of time: Not only does Lady Brett look bad in an era of feminism, but the character of Robert Cohn is treated badly, leading to the charge the Hemingway was anti-Semitic; and bullfighting, which Hemingway celebrated in this book and in several short stories, has come to be seen by the wider world as barbaric.

Hemingway himself, though an incredibly talented writer, was a barbaric man, who never met a human being, man or woman, that he didn't want to hit; never met a woman that he didn't want to have sex with; and never met an animal he didn't want to shoot. On July 2, 1961, he shot and killed the most dangerous animal he ever faced: Himself. He was his own worst enemy, and he was just short of turning 63.

Wednesday, October 21, 2026

Top 10 World Series with the "Smallest Markets"

The 2026 World Series will be between the Milwaukee Brewers, Champions of the National League, and the Tampa Bay Rays, Champions of the American League.

The Rays previously won Pennants in 2008 and 2020; the Brewers, only in 1982. Neither has ever won a World Series. One will win their 1st in the next few days.

And they will face each other as the smallest-market matchup in World Series history.

These are, as sports management puts it, "small markets." Although, with the way sports is presented these days, there really is no longer any such thing as a "small market."

Note that this is based on how small the market was at the time; and that this is tilted toward the post-expansion era. When it was just the "Original 16," people thought in terms of "cities," not "metropolitan areas" or "markets."

Note also that it's the cities' rankings in Major League Baseball, not overall in America; that I'm not counting the Canadian cities of Toronto and Montreal; and that changes in a city's ranking can be not just due to changes in population, but due to moving, although the only moves since 1971-72 have been the Montreal Expos to Washington in 2004-05 and the Oakland Athletics to Sacramento in 2024-25.

1. 2026: Milwaukee, 26th, vs. Tampa Bay, 16th. Total: 42.
2. 1985: Kansas City, 24th, vs. St. Louis, 12th. Total: 36.
3. 2006: St. Louis, 18th, vs. Detroit, 13th. Total: 33.
4. 1982: Milwaukee, 21st, vs. St. Louis, 12th. Total: 33.
5. 2013: St. Louis, 20th, vs. Boston, 12th. Total: 32.
6. 2014: Kansas City, 23rd, vs. San Francisco, 6th. Total: 29.
7. 1980: Kansas City, 24th, vs. Philadelphia, 4th. Total: 28.
8. 2016: Cleveland, 24th, vs. Chicago, 3rd. Total: 27.

And 4 others were tied for the 9th and 10th spots, with 26:

2008: Tampa Bay, 20th, vs. Philadelphia, 6th. 
2007: Denver, 19th, vs. Boston, 7th.
1997: Cleveland, 14th, vs. Miami, 12th. 
1987: Minneapolis, 14th, vs. St. Louis, 12th. 

Detroit and St. Louis had faced each other 3 times before 2006, but the last of those was in 1968, when there were just 20 teams in MLB.

The smallest-market matchups in the other sports? In the NHL, we just had it this year, when the Carolina Hurricanes, of the Raleigh-Durham area, beat the Vegas Golden Knights.

In the NBA, it was last year, when the Oklahoma City Thunder beat the Indiana Pacers, of Indianapolis. And in the NFL, it was in 2010, in Super Bowl XLIV, when the New Orleans Saints beat the Indianapolis Colts.

World Series Where Both Teams Had Never Won Before

The 2026 World Series will be between the Milwaukee Brewers, Champions of the National League, and the Tampa Bay Rays, Champions of the American League.

The Rays previously won Pennants in 2008 and 2020; the Brewers, only in 1982. Neither has ever won a World Series. One will win their 1st in the next few days.

World Series where both teams had never won before:

1903 Boston Americans (Red Sox) beat Pittsburgh Pirates
1905 New York Giants beat Philadelphia Athletics
1906 Chicago White Sox beat Chicago Cubs
1907 Chicago Cubs beat Detroit Tigers
1920 Cleveland Indians (Guardians) beat Brooklyn Robins (Dodgers)
1980 Philadelphia Phillies beat Kansas City Royals
2026 Milwaukee Brewers vs. Tampa Bay Rays

1992 sort-of counts: The Toronto Blue Jays had never won a Pennant before; while the Atlanta Braves had won the World Series, but in Boston and Milwaukee, not yet in Atlanta.

2002 sort-of counts: The team then known as the Anaheim Angels had never won a Pennant before; while the San Francisco Giants had won the World Series, but in New York, not yet in San Francisco.

2010 sort-of counts: The Giants were in it again, and the Texas Rangers had never won a Pennant before.

It hasn't happened in the NFL since 1982, when the San Francisco 49ers beat the Cincinnati Bengals in Super Bowl XVI.

It sort-of happened in the NBA in 2025: The Oklahoma City Thunder beat the Indiana Pacers in the Finals. The Pacers won 3 titles in the ABA, but are now 0-2 in NBA Finals. The Thunder last won in 1979, as the Seattle SuperSonics. If you don't count that, then it last happened in 2006, when the Miami Heat beat the Dallas Mavericks.

The NHL's last occurrence was relatively recent: In 2023, the Vegas Golden Knights beat the Florida Panthers to win the Stanley Cup.