ST. PETERSBURG, Fla. — As the Rays got set to take the field Tuesday night for Game 4 of the World Series against the Brewers, they were headed toward making history, either improbable or ignominious.

With wins Tuesday and Wednesday at the Trop and Friday and Saturday in Milwaukee, the Rays would become the first of 26 teams to fall behind 3-0 in a best-of-seven World Series (and the second of 44 in any playoff round) and end up celebrating.

With a loss anywhere along that treacherous path, they would become the only team still seeking its first championship that has lost the Series three times. They also would join the Dodgers and Tigers as teams who lost at least their first three World Series.

There is obviously a philosophical or even existential debate that can be held about whether it’s better to get there and lose or never get the chance.

But the reality is, the Rays went home disappointed the first two times they made the Series and seemed headed toward a third.

2008: You always remember your first time

The Rays were mostly young and everything was new in 2008, when they made the remarkable transformation from perennial losers (never winning more than 70 games in any of their first 10 seasons) to championship contenders after winning 97 games and their first American League East title.

They became the second team in major league history and the fifth in the four major pro sports to go from having the worst record in the league one year to the championship series the next. The others were the 1991 Atlanta Braves, the 1958-59 Minneapolis Lakers, the 1958-59 Toronto Maple Leafs and the 1949-50 New York Rangers.

They beat the White Sox 3-1 in the AL Division Series and survived a seven-game AL Championship Series against the Red Sox — blowing a 7-0 lead in what would have been a clinching Game 5 at Fenway Park, then letting Boston extend the series to seven games, which team officials said factored in the Rays’ 4-1 loss to the Phillies in the World Series, which also was marred by brutal weather conditions.

Though obviously wanting badly to win, Rays officials (including a former baseball operations intern recently promoted to full time named Erik Neander) took some satisfaction in bringing the World Series to St. Petersburg.

“Just the environment, the excitement, just in some ways in Game 1, the reality hitting that for the first time there’s proof and a demonstration you could win here,” Neander, now the veteran baseball operations president, said Monday, before the first Series games at the Trop in 18 years.

“All the themes, the Ray Hawk (haircuts), and just all the excitement that came with it. There’s only one first run like that and there will only be one first championship, and if that comes hopefully it’s here. But the entire experience this year, in so many ways, has you thinking back to 2008 a lot.”

Scott Kazmir, who threw the first pitch in the first World Series game played at the Trop, was back Monday as a member of the Commissioner’s Ambassador Program, a group of 20 former players who represent MLB at various events, and having flashbacks.

“Everything feels the exact same as 2008,” he said. “This is going to be special to see a World Series game here again after 18 years.”

The Rays lost the opening game after Kazmir put them in a slight early hole, then rebounded to win Game 2 — which going into Tuesday was their only Series victory at the Trop — by striking first.

Aki Iwamura led off with a walk, BJ Upton singled and Carlos Pena and Evan Longoria followed with RBI groundouts. They added on with an Upton RBI single and a Jason Bartlett bunt that scored Cliff Floyd. Starter James Shields worked into the sixth, and relievers Dan Wheeler and rookie David Price took it from there.

The games in Philadelphia, though, were a mess.

The Rays got walked off in a weather-delayed Game 3, falling behind early, tying it late, then losing in the ninth at nearly 2 a.m. on a sequence that included reliever J.P. Howell hitting a batter, catcher Dioner Navarro making an errant throw to second and Carlos Ruiz hitting a dribbler up the third-base line that Longoria couldn’t make a play on.

After a blowout loss in Game 4, the Rays battled the Phillies and the elements in Game 5, playing in bitter cold (47 degrees at the start) and at times heavy rain.

Down again early, the Rays rallied to tie the score in the top of the sixth. Upton singled with two outs off Cole Hamels, sloshed his way to steal second, then somehow dodged the puddles to race home on Pena’s single.

“Who knows how, because it was so wet, he almost had to like tip-toe himself around the bases and we tied the ballgame,” Pena recalled last week.

“I go crazy. We’re all excited. And they pulled the tarp (putting the game in a weather delay). I think the delay was the MVP for the Phillies, because we had momentum right then and there when we tied the ballgame. We had it. And I thought if we won that game we would have won the World Series. We would have come back to the Trop and we had momentum, and it would have been over.”

Instead — after the Rays had to relocate from their Philadelphia hotel to the historic Hotel Du Pont in Wilmington, Del., — play resumed two nights later.

The Phillies got a run in the bottom of the sixth off Grant Balfour. The Rays retied the score in the seventh on a homer by Rocco Baldelli. The Phils went back ahead in the seventh with hits off Howell and Chad Bradford and hung on from there, Brad Lidge striking out Eric Hinske to end the Rays’ dreams.

“You go on these magical rides and you’re never expecting it to end, and that one did,” Neander said. “It took a little while. It was a slow death in Game 5. But just an unbelievable group of guys and staff that accomplished that, and we’re fortunate to have one just like them here in 2026.”

2020: A different world, and World Series

The Rays’ 2020 World Series experience was entirely different because the world was different, given the extensive restrictions due to the global pandemic.

The Rays took advantage of the abbreviated 60-game schedule to roll through the season at what over a full year was a 108-win pace. They then beat the Blue Jays (2-0 in the wild-card series), Yankees (3-2 in the ALDS) and Astros (4-3 in the ALCS after being up 3-0) to get to the World Series against the Dodgers, played before a limited number of fans in Arlington, Texas.

“We made the absolute most of the circumstances,” Neander said. “And, of course, there was more important stuff going on in the world.”

The Dodgers won the opener as the teams alternated wins through the first three games, then the Rays pulled even in Game 4 with Brett Phillips playing the starring role in one of the wildest endings to any Series game.

The Rays were down 7-6, had two on with two out and Phillips at the plate against Kenley Jansen with a 1-2 count.

Phillips slapped a single to center, scoring Kevin Kiermiaer with the tying run, then — after errors by center fielder Chris Taylor and catcher Will Smith — the winning run after Randy Arozarena, who fell going around third, got back up to slide headfirst into home to deliver the 8-7 walk-off win.

Phillips celebrated with a now iconic airplane run through the outfield and uttered the classic phrase on TV that has become his motto and led to a line of merchandise, “Baseball is fun.”

The Rays lost a close Game 5, then the Series in Game 6 known more than anything for manager Kevin Cash’s decision to pull starter Blake Snell with a 1-0 lead, one on and one out in the sixth.

As much as that move was, still is and may forever be scrutinized and criticized, the bigger issue was that heavily used reliever Nick Anderson failed to do his part. Anderson gave up a double to put two men in scoring position, threw a wild pitch that let one run in, then allowed a fielder’s choice grounder that gave the Dodgers a 2-1 lead and the path to a 3-1 Series-clinching victory.

Neander defended Cash’s call — “He felt he made the decision that was right for that club, and for anyone that was paying attention to that team it is what he did all year long” — and said the Series should be remembered for much for than that.

“Some of it’s a choice, and I think the vast majority of our fans choose to find ways to celebrate a lot of the special moments that happened that year, including Brett’s huge moments in Game 4,” Neander said, noting that Phillips, who now works for the team in an ambassador-type role, still “gets plenty of love” as he walks around the Trop during this Series.

“We won two games and they won four, so there’s a lot of moments that over the course of a series like that you can look back on and point to,” Neander said.

“More than anything, yeah, you want to win it. But if not that, it’s a privilege to play in it and it’s a huge accomplishment in and of itself. Without question, we made the most of it, and in many ways, going through that you could argue that was a harder, a more challenging experience to navigate. So, unbelievably proud of that group, as 2008, as this one here.”

Unfortunately for the Rays, they may have something else in common.

Most World Series lost

14 — Dodgers, Yankees

12 — Giants

8 — Cardinals, Cubs

7 — Tigers

6 — Braves, Phillies

5 — Athletics

4 — Guardians/Indians, Orioles, Reds, Red Sox

3 — Astros, Mets, Twins

2 — Padres, Pirates, Rangers, Rays*, Royals, White Sox

1 — Blue Jays, Brewers*, Diamondbacks, Rockies

*As of Monday

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