Jeff Bagwell began his career in the Red Sox organization, the team he grew up cheering for as a kid in Connecticut. Jose Cruz was a little-known outfielder when the Astros threw some cash at the Cardinals to get him to join their club. And Justin Verlander was already one of the top pitchers in baseball by the time the Astros acquired him.

The Astros’ history of trades is as colorful and confounding as any team in baseball, with Houston sending away Joe Morgan, Rusty Staub and Mike Cuellar as young players and watching them blossom into stars elsewhere. They’ve had some huge trade wins, as well, including the 2016 deal that brought future American League Rookie of the Year Yordan Alvarez over from the Dodgers in exchange for relief pitcher Josh Fields.

That’s a deal that might one day wind up as one of the best for the Astros, but it doesn’t yet crack the five best trades in club history:

1) Aug. 30, 1990: Astros acquire Jeff Bagwell from the Red Sox for RHP Larry Andersen

Considered one of the most lopsided trades in baseball history, the Astros plucked a future Hall of Famer away from the Red Sox for a journeyman reliever. Bagwell came up as a third baseman with Boston, but he was blocked in the organization by Scott Cooper and Tim Naehring. So the Red Sox sent him to Houston in return for Andersen, a solid relief pitcher.

Bagwell was the National League Rookie of the Year in 1991 at 23 years old, won the NL Most Valuable Player in 1994 and was one of the greatest sluggers of his generation. He played 15 years in Houston and was a career .297 hitter with 449 homers, 1,529 RBIs and 202 stolen bases, in addition to his terrific defense and skillful baserunning. Andersen spent 17 seasons in the big leagues and appeared in 15 games down the stretch for Boston in 1990, helping them reach the playoffs. Still, it’s a deal the Red Sox would like to have back.

“He was pitching well that particular year,” said Bill Wood, the Astros general manager who pulled off the deal. “He was a valuable piece to anyone in the hunt, and Boston, of course, was interested in him, and we had our scouts look at the Boston system very closely, and Bagwell was a guy that we really zeroed in on. We did not zero in on the guys that Boston kept throwing at us as potential guys ahead of Bagwell in the system at Triple-A.”

When Andersen was called into manager Art Howe's office, he knew the drill. After all, he had been traded twice previously in his career.

"I said, 'Who'd you guys get?'" Andersen said. "[Howe] said, 'We got a third baseman from Double-A.' I was like, 'I'm pitching good and I'm one of the best setup men,' I felt like, at the time, and coming off two sub-2.00 ERAs two seasons in a row.

"I was like, 'Really, all they got was a Double- A third baseman for me?' After the fact, Bagwell is looking back and going, 'You've got to be kidding me? I'm going into the Hall of Fame and all they got was this 40-year-old reliever for me?' It kind of goes hand in hand. We joked it up, we laughed about it, but it's all been good for me, and I'm sure him going into the Hall of Fame is good for him, too."

2) Aug. 31, 2017: Astros acquire RHP Justin Verlander from the Tigers for OF Daz Cameron, P Franklin Perez and C Jake Rogers

August 2017 was a rough month for the Astros, who ended July with a 16-game lead in the AL West but went 11-17 in August and were displaced at the end of the month by Hurricane Harvey, which ravaged the Houston area. Any malaise around the team was swiftly gone as the final seconds of August ticked away and the Astros pulled off a blockbuster trade by acquiring Verlander, the former Cy Young Winner and Most Valuable Player from the Tigers.             

Former Astros general manager Jeff Luhnow, who was in Los Angeles for the Astros’ series against the Angels and remained there for a few days, was in hot-and-cold talks with the Tigers. As the midnight Eastern deadline approached, the two teams agreed on a trade package for Verlander and the money, but the Tigers still had to convince Verlander to waive his no-trade clause. The Astros tried to convince him, too. Pitcher Dallas Keuchel made a recruiting call to Verlander with hopes of having him join him in Houston to make a run at the World Series ring that had eluded both of them.

“At one point I was kind of pacing back and forth in my living room -- it was just [then-fiancée] Kate [Upton] and I -- and I'm going, 'Trust your instincts, trust your instincts. What are your instincts telling you?'" Verlander said. "I was just so caught in between with emotion and excitement of a new ballclub, and ultimately, it came down to winning and joining an organization that's set up to win for a long time."

Luhnow’s phone finally rang at 9:14 p.m. PT -- 14 minutes after the deadline passed. Major League Baseball had approved the deal after receiving verification from Verlander two seconds shy of the deadline. Verlander was an Astro.

Verlander went 5-0 with a 1.06 ERA in five regular-season starts for the Astros in ’17. He carried his hot hand into the playoffs, making his first career relief appearance in Game 4 of the AL Division Series at Fenway Park and threw 2 2/3 innings to eliminate the Red Sox. He won both of his starts in the AL Championship Series against the Yankees and was named MVP of the ALCS.

He went 16-9 with a 2.52 ERA and led the AL with 290 strikeouts in 2018, finishing second in AL Cy Young voting. The next year, he won the Cy Young Award, going 21-6 with a 2.58 ERA and 300 strikeouts in 223 innings. He also reached 3,000 career strikeouts that year and threw his third career no-hitter. 

3) Dec. 10, 1982: Astros acquire RHP Mike Scott from the Mets for OF Danny Heep

A ho-hum trade at the Winter Meetings in 1982 turned out to be a doozy for the Astros. Scott went just 15-17 in his first two years in Houston before he learned the split-fingered fastball from Tigers pitching coach Roger Craig and turned around his career.

Scott went 18–8 with a 3.29 ERA in 1985 and quickly became a star. He went 18–10 and led the Majors in ERA (2.22), shutouts (five), innings pitched (275 1/3) and strikeouts (306) in 1986 en route to the Cy Young Award. He sewed up the award when he pitched a no-hitter to clinch the National League West division title against the Giants on Sept. 25, 1986.

Allegations that Scott was scuffing the baseball to give him an advantage followed him throughout that season with Craig -- then the manager of the San Francisco Giants -- leading the charge.

Scott and the Astros steadfastly denied the balls were being doctored. Nothing was proven.

Scott won 110 games in nine seasons for the Astros, including a 20-win season in 1989, and had his number retired by the club in 1992.

4) Aug. 1, 2016: Astros acquire DH Yordan Alvarez from the Dodgers in exchange for RHP Josh Fields

In what appeared to be an insignificant deal at the time, the Astros wound up with a cornerstone player in Alvarez by sending Fields to the Dodgers. Alvarez unanimously won the 2019 AL Rookie of the Year Award for Houston and he emerged as a force in the middle of the lineup in 2021, hitting 33 homers with 104 RBIs. He helped the Astros win the AL pennant in 2019 and ’21 (he played in only two games in ’20).

Alvarez was signed by the Dodgers as an undrafted free agent on June 15, 2016, and he had yet to play a game in their system before he was dealt to the Astros. Fields pitched rather well during his three seasons with Los Angeles, but he is best known in Dodgers history for giving up back-to-back homers to Jose Altuve and Carlos Correa, followed by a double by Yuli Gurriel, in the 10th inning of Game 2 of the 2017 World Series. Fields was removed from the game without recording an out. That performance only tilts the trade in the Astros’ favor even more.

5) Jan. 13, 2018: Astros acquire RHP Gerrit Cole from the Pirates for RHP Joe Musgrove, RHP Michael Feliz, OF Jason Martin and 3B Colin Moran

Coming off the 2017 World Series title, the Astros bolstered their pitching staff by adding Cole from the Pirates. He transformed the way he pitched in Houston and went 15-5 with a 2.88 ERA in 32 starts in ’18 before posting one of the best pitching seasons in Astros history in 2019.

Cole overcame a slow start to blossom into an unstoppable force, going 20-5 with 326 strikeouts and a 0.89 WHIP in 212 1/3 innings pitched, finishing a close second in the 2019 AL Cy Young race to his teammate, Verlander.

After starting the year by going 4-5 with a 4.11 ERA in his first 11 starts, Cole went on one of the most dominating stretches in team history. He went 16-0 with a 1.78 ERA in his final 22 starts. The Astros won each of the final 13 games Cole started in the regular season, but the season ended bitterly with Cole waiting in the bullpen as the Astros blew Game 7 of the World Series. He signed with the Yankees two months later.