Greg Maddux was just 20 years old when he threw his first big league pitch at Wrigley Field in 1986. A September call up, Maddux pitched in six games that season.

His first two years Maddux went 8-18. In 1988 he went 18-8 to even his record at .500. He also made his first All Star team. Maddux won 95 games in his first stint with the Cubs. The right-hander pitched in two All Star Games and earned the first of his four consecutive Cy Young Awards before leaving for Atlanta.

He eventually returned to the Windy City for parts of three seasons and win a total of 133 games for the Cubs.

Shown here is the very first Topps card on which Greg Maddux appeared. Printed after the 1986 season, Maddux’s first in the big leagues, this rookie card is signed boldly by the 355-game winner.

According to Rick Sutcliffe, Greg Maddux chose a beanball over the big leagues. Maddux’s Cub teammate from 1986-1990, Sutcliffe tells a great story about Maddux’s 24th career game.

The Cubs faced off against the Padres on July 7, 1987 at Wrigley Field.

“Greg Maddux was pitching that day and he’d been told before the game that if he doesn’t win, he’s going back to the minor leagues,” Sutcliffe explains.

In the top of the fourth Chicago’s Andre Dawson was hit by a fastball up and in.

“I remember Eric Show was pitching and hit Andre right in the face,” Maddux recalled. “Hawk was our main guy. I remember him laying there right on home plate kind of knocked out. Then he came to and spit a bunch of blood on the plate and then he started looking for Eric Show.”

After a bench-clearing brawl, Sutcliffe said he found the 21-year old Maddux and had a chat.

“I said, ‘Hey, here’s what you’re doing. You’re going to go get three outs, you’re going to get the win and then in the sixth inning you do whatever you want.’ He looked at me and went, ‘No’. He goes, ‘I’m hitting the first guy.’

“I said, ‘If you don’t get three outs, they’re going to send you to the minor leagues.’

“And with tears in his eyes he said, ‘I don’t care if I get another win.’

“And I’m getting goosebumps right now. I can still see his face.”

San Diego’s Benito Santiago led off the top of the next frame.

“He hit him,” Sutcliffe continues. “He got sent down to the minors and I think he had the minimum 15 days or whatever it was. He was back in the big leagues and he never saw that minor league bus again after that.”

Maddux had no regrets.

“I certainly would’ve lost a ton of respect if I didn’t hit anybody,” Maddux said later. “That was way more valuable than any win I could have ever gotten.”

It’s a great story to be sure.

Before the start of the 1982 season Andre Dawson received the check shown above from the Major League Baseball Players Association for the sum of $2,527. A nice chunk of change for the 27-year old outfielder.

For more on Dawson, click here.

After winning the Cy Young Award in 1992 with the Cubs, Greg Maddux signed with the Braves that December. In Atlanta he stayed on the path to Cooperstown. His first three seasons with the Braves resulted in three Cys, bringing his total to four in four years.

During the run, Maddux won 75 games with a 1.98 ERA and an ERA+ of 202. His 11 years in Atlanta included 194 wins, a 2.63 ERA, 10 Gold Glove Awards, 11 postseason appearances, and one World Series title.

Shown here is Maddux’s contract extension with Topps Chewing Gum. He was on his way to stardom when he signed this on May 3, 1988. The first year of the extension saw an 18-win season and Maddux’s first All Star appearance.

By the time the contract expired at the end of the 1991 season, Maddux had two of his record 18 Gold Glove Awards and his first $1 million contract. A 355-game winner, Maddux was a first-ballot Hall of Fame selection.

The Cy Young Award was originated in 1956 to recognize pitching excellence. Through 1966 it was given to the singular best twirler in the major leagues. Then in 1967, it was expanded to honor a pitcher in each league.

Through the award’s first 70 years four pitchers have been dominant enough to earn the nod four times. Roger Clemens holds the record with seven Cy Young nods. Second on the list left-hander Randy Johnson with five. Greg Maddux and Steve Carlton round out the list of those with as many as four Cy Young Awards.

Maddux earned his plaques in successive seasons starting in 1992. During the four-year run his ERA+ was an astounding 202. Looking at traditional stats, Maddux went 75-29 with a 1.98 earned run average.

In addition to his four Cy Youngs, the right-hander also finished in the top-5 in balloting in five other seasons. Maddux’s 4.92 career Cy Young shares ranks fourth all-time behind Clemens, the Big Unit, and Justin Verlander.

In the collection is the game-used lineup card from Randy Johnson’s 300th strikeout of the 1993 season. Signed by the 6’10” southpaw, the card also features the signature of manager Lou Piniella. Though the Mariners lost the game in 12 innings, Johnson did his part, allowing only two runs in ten innings of work. He struck out 13 and finished the game with 301 Ks.

Only Johnson and Clemens have more Cy Youngs than Maddux. Johnson first earned the honor in 1995, the last of Maddux’s Cy Young seasons. Starting in 1999 the Big Unit took home the award four straight seasons, matching Maddux’s feat.

Greg Maddux helped his teams make the postseason in 13 seasons. Once they got there, Maddux was less than dominating.

In 35 postseason games, Maddux went 11-14 with a 3.27 ERA. His won/loss record dips to 6-11 in the League Championship Series and World Series.

In 1995 Maddux earned his lone World Series ring. That October he controlled the hitters. In 5 starts he pitched threw 38 innings and allowed only 4 earned runs. His postseason record in ’95 was 3-1 with a .095 ERA.

Shown here is Bobby Cox‘s lineup card from Game 3 of the 1998 NLCS. After losing the first two games of the 1998 NLCS, Cox handed the ball Maddux to get the Braves back in the series.

The right-hander threw 81 pitches through five innings before being lifted with his team trailing 2-1. The Padres tacked on two more runs and beat the Braves 4-1.

Though the Braves won the next two games of the series, San Diego knocked them out of the post season in Game 6.

Maddux teamed with John Smoltz and Tom Glavine to form one of the mightiest pitching trios in baseball history.

Baseball’s history sets it apart from other professional sports in America. Fans use comparisons of players of different eras to debate Hall of Fame worthiness. Because of the history, great players from the present-day become intertwined with legends of the past.

In the collection is this lineup card that hung in the Braves dugout during Atlanta’s contest vs. the Houston Astros on August 7, 2001. The game brought Braves starter Greg Maddux into a conversation that included the mythical Cy Young, a man from Cooperstown’s inaugural class of 1936 in Christy Mathewson, and Hall of Fame hurlers Red Faber and Jack Morris.

Maddux came into the game with 64 1/3 consecutive innings without a walk, just 3 2/3 innings short of the National League record set by Mathewson in 1913 and equaled by Randy Jones in 1976.

In the fourth inning, Maddux passed the two men and made the record his own. The first-ballot Hall of Fame selection extended mark to 72 1/3 innings before issuing an intentionally pass in his next start to Arizona’s Steve Finley to stop the streak.

Today Maddux still holds the Senior Circuit’s mark for consecutive innings without a walk.

By picking up the win in this game, Maddux became the second pitcher in Major League Baseball history to win 15 or more games in at 14 straight seasons, trailing only Cy Young who won at least 15+ for fifteen straight years from 1891-1905.

In each of his next three seasons Maddux continued his winning ways. His 17 consecutive seasons with 15 or more wins is the MLB record. In terms of non-consecutive 15-win seasons, Maddux and Young top the list with 18.

By 2001, Maddux was climbing the career wins leaderboard, passing Hall of Fame pitchers along the way. The lineup card above is from his 255th victory. The win pushed him past White Sox great Red Faber, a 1964 inductee and Cooperstown class of 2018’s Jack Morris.

For aficionados of America’s National Pastime, this Sunday afternoon game of August 7, 2001 highlighted baseball’s timeline, spanning the 1800’s of Cy Young’s career, the Deaball Era of the teens with the great Christy Mathewson, into the 20’s and 30’s when Faber pitched, up through Jack Morris’ heyday of the 1970’s and 80’s and onto the next millennium to the career of Greg Maddux.

Greg Maddux struck out Omar Vizquel in the third inning of the July 26, 2005 contest for his 3,000th career K. That made him the ninth 300-game winner with 3,000 strikeouts.

Since the right-hander achieved the feat, only Randy Johnson has equaled it. By the time he hung up his spikes, Maddux boasted 355 wins and 3,371 strikeouts.

The above image shows a handwritten letter by the original fraternity member of the 300-win/3,000 strikeout club. In it Walter Johnson thanks Hall of Fame executive Ford Frick for a lifetime pass to all major league contests.

Fergie Jenkins and Greg Maddux became the first Cubs hurlers to have their jersey numbers retired. Both men wore #31 and saw their number retired in 2009.

Jenkins holds the top spot in Cubs franchise history in pitchers’ WAR, starts, and strikeouts. He ranks 4th in shutouts and 5th in wins. Jenkins also holds the distinction as the Cubs first Cy Young Award winner.

Maddux earned the Cy Young for the Cubs in 1992, the fourth Chicago NL hurler to do so. One hundred and thirty three of his 355 victories came in a Cubs uniform.

Shown here is the document that consummated the trade of Jenkins to the Cubs on April 21, 1966.