Short of a World Series ring, Zack Greinke has accomplished nearly everything in his 18-year career. The right-hander is a Cy Young Award winner, a six-time All-Star, a six-time Gold Glove winner and a two-time Silver Slugger. The 38-year-old won the ERA title twice and has a career 3.41 ERA with 3,110 innings pitched, 2,809 strikeouts and 219 wins. His 73.1 career WAR, according to Baseball Reference, ranks 86th all time, tied with Jim Thome.

Greinke has established himself as one of the best pitchers of this generation and as one of the most interesting players in baseball with countless unique stories told by his teammates and coaches.

Now in the twilight of his career, here are 10 moments that helped define Greinke’s career:

1. Cy Young Award
2009
There wasn’t much for Royals fans to be excited about in 2009, but Greinke was a bright spot in Kansas City. After posting a Major League-leading 2.16 ERA, Greinke won the American League Cy Young Award, becoming the first Royal to do so since David Cone in 1994.

It was quite the turnaround for Greinke, who led the AL in losses (17) in 2005 and quit baseball for six weeks the following year for his mental health. But he found joy in baseball again and made his way back. He finished 2009 with a 16-8 record for the last-place Royals, allowed just 11 home runs all season, led the Majors with a 2.33 FIP and led the AL with a 1.073 WHIP.

2. 1.66 finishes No. 2
2015
It seems crazy to even say that a pitcher who posted the lowest Major League ERA in 20 years didn't win the Cy Young Award, but that’s how tight the National League race was in 2015. Greinke, whose 1.66 ERA was the best in baseball, finished second to the Cubs’ Jake Arrieta, whose 0.75 ERA in the second half was historic. Greinke’s teammate, Clayton Kershaw, led the league in strikeouts (301) and innings pitched (232 2/3) -- and finished third.

The final ballot was far from a travesty, but Greinke was certainly deserving for his incredible season. Then 32 years old, he was excellent the entire season. He didn’t allow a run in 11 of his 32 starts and went at least six innings in each of those 11 starts. He also had a streak of 45 2/3 scoreless innings at one point.

Greinke was angling to become the sixth pitcher in Major League history to win a Cy Young Award in each league. While that didn’t work out, he did become a free agent after the season and signed a six-year, $206.5 million deal with the D-backs.

3. Pitchers who rake
June 10, 2005
It’s no secret that Greinke has always loved hitting. He was a terrific shortstop on the mound, and he said before that he would have liked to make it in the big leagues as an everyday player. The problem was he was just too good of a pitcher. So when he got to hit, it fired him up.

In 2005, the Royals visited Arizona. It was only Greinke’s second game as a hitter. And he called his shot. He told general manager Allan Baird and manager Buddy Bell before the game that he was going to hit a home run. Baird asked him if that was a guarantee.

“Absolutely guaranteed,” Greinke said with a smile.

When Greinke got to the mound that night, he got pulverized. By the end of the fourth inning, he had given up 11 hits (seven for extra bases), two walks and seven runs. His spot was coming up in the top of the fifth, but he wasn’t lifted for a pinch-hitter. Bell wanted to see if the young Greinke could pull himself out of the mess, so Greinke stepped to the plate to hit for himself.

On the second pitch from D-backs starter Russ Ortiz, Greinke would later say he closed his eyes and swung as hard as he possibly could. He sent the ball soaring to deep left-center field. By the end of the day, Greinke had called his shot for his first big league home run and set two Royals records by allowing 15 hits and 11 runs in a game.

At the end of 18 seasons, Greinke has nine home runs to his name and two Silver Slugger Awards, with the Dodgers (2013) and D-backs (’19). He’s also a threat on the basepaths with nine career steals -- and he admitted the only milestone he wants to reach is 10 homers and 10 steals.

4. 2,000th strikeout
Aug. 24, 2016
In the fourth inning of the D-backs’ game against the Braves, Greinke threw a two-strike low slider to Freddie Freeman, who whiffed at the pitch for the first out of the inning. It wasn’t a big deal to Greinke at the moment -- he was just trying to get through a rough outing -- but in the grand scheme of things, it was another milestone for the potential Hall of Famer: Strikeout No. 2,000. At the time, Greinke joined 77 other pitchers to reach 2,000 strikeouts, and he became the sixth-fastest among active pitchers to reach that mark, achieving the feat in 385 games.

5. 200th win
Aug. 18, 2009
Much like his 2,000th strikeout, Greinke wanted little fanfare when he notched his 200th win, but his Astros teammates made sure to toast the starter for it. Greinke held the A’s to one run and four hits in seven innings of a 4-1 victory at the Coliseum, and with the win, the right-hander became the third active pitcher at the time to reach 200 wins. Justin Verlander (219) and C.C. Sabathia (251) were the only others. Now, Greinke and Verlander are the only two active players to reach the feat -- but Max Scherzer (190) and Adam Wainwright (184) aren’t far behind.

6. 2014 NLDS
Oct. 4, 2014
Greinke has pitched 113 innings of postseason baseball, but Game 2 of the National League Division Series might be his best playoff game to date. Needing a win to tie the series against the Cardinals, Greinke delivered seven shutout innings with just two hits allowed -- also the number of hits he had against the Cardinals that day. Greinke no-hit the Cardinals until the fifth, when Kolten Wong doubled, but Greinke bounced back by getting back-to-back strikeouts of Randal Grichuk and Lance Lynn.

7. 15-strikeout game
Aug. 25, 2009
Nearly every time Greinke walked to the mound during his Cy Young Award season, he was unpredictable and unhittable. He was dominant again on Aug. 25, 2009, against Cleveland -- and ended up in the record books. Greinke struck out a then team-record 15 in eight overpowering innings, passing his career high with 12 strikeouts in the first six innings and breaking Mark Gubicza’s 21-year-old team record of 14 in the seventh. Greinke doesn’t hold the Royals’ record anymore -- Danny Duffy struck out 16 in a game against the Rays in 2016 -- but the late-August performance put a bow on his Cy Young season.

8. 13 strikeouts in five innings
Sept. 25, 2012
Greinke spent a season and a half in Milwaukee before the Brewers traded him to the Angels in a Trade Deadline deal in 2012. He joined the Angels for the stretch run and made history on Sept. 25 against the Mariners, when he struck out 13 batters in just five innings. According to ESPN Stats, Greinke became the first pitcher in the live ball era (since 1920) to strike out 13 batters in a start that lasted only five innings.

Greinke had a high pitch count that day -- 110 by the end of his outing -- leading to his shorter start. But the Angels' bullpen picked up where he left off and struck out seven more batters, tying a Major League record with 20 strikeouts in a nine-inning game.

9. Slow it down
April 12, 2021
Greinke is not afraid to mix up the speeds on his pitches, and he took it to another level early in 2021. Perhaps frustrated after giving up three home runs to the Tigers, Greinke tried something new in the top of the fifth inning to Renato Núñez: a 51.5 mph pitch.

Greinke’s eephus, his slowest pitch since tracking began in 2008 that wasn’t an intentional ball, went for a called strike, and Núñez grounded out weakly two pitches later. Núñez had homered two innings earlier on a slider -- 30 mph faster than the eephus.

10. Signed, sealed, delivered
Aug. 12, 2020
It wouldn’t be a Greinke list if we didn’t have at least one of the times his personality came out on the field. In a game against the Giants during the 2020 season -- when there were no fans in the stands because of the coronavirus pandemic -- Greinke gave hand signals to catcher Martín Maldonado and could even be heard talking about changing up the signs.

Greinke had given hand signals to Maldonado earlier in the year in an effort to speed up the game, especially when there was a runner on second base. He had signaled his signs with his right hand in his previous start, too, and threw six scoreless innings against the A’s. It’s not typical for a pitcher to signal to the catcher what he’s going to throw -- but Greinke isn’t typical.

"You probably won't see another guy like Greinke in your lifetime or my lifetime either,” Astros manager Dusty Baker said. “This guy sure can pitch.”