Just a week ago—seems a lot longer—the Royals dealt Whit Merrifield to the Toronto Blue Jays, thus ending the former 9th-round pick’s six-and-a-half year tenure in Kansas City. In that time, which began in 2016, the Royals never finished with a winning record, and yet Merrifield played dang near every game, including 553 in a row.

His departure just adds to the list of saddest in Royals history.

Here’s a look at the 16 saddest departures in Kansas City Royals history. When I say “departure,” I’m talking everything but retirement. A trade, a release, leaving in free agency, getting waived—that makes you eligible for this list.

First, some guys who just missed.

Honorable Mention

Alcides Escobar

Greg Holland (the first time)

Amos Otis

Kelvin Herrera

John Mayberry

Steve Balboni

Raúl Ibañez (the first time)

Jermaine Dye (just missed!)

The Top 16 Saddest Departures

16. Whit Merrifield, 2022

With the team in the throes of a youth movement, the Royals finally moved on from Whit, dealing him to Toronto for a couple of prospects. It would’ve been sadder had, just days before, Whit not said something that was better left unsaid. Regardless, he played valiantly for some pretty bad teams, accumulating around 17.0 WAR in over six seasons, making two All-Star teams, leading the league in hits twice, doubles once, triples once, and stolen bases three times.

15. Lou Piniella, 1974

On the very first Royals team, the 25-year-old Piniella won Rookie of the Year after slashing .282/.325/.416. In 1974, a year in which he’d lead the AL in doubles, he made his only All-Star Game. The Royals traded him in December of 1973 to the Yankees for a past-his-prime pitcher only to watch Piniella play 11 seasons in pinstripes, capturing two World Series titles.

14. Wade Davis, 2017

In December of 2016, the Royals struck a deal with the Cubs, sending the middle of a once-vaunted bullpen to Chicago for a young slugger. This deal truly signaled the start of the Royals rebuild, which is currently ongoing. Davis, who came over with James Shields from the Rays before 2013, blossomed with the Royals, and was particularly lights out in the 2014 and 2015 postseasons. allowing just one earned run in 25 innings while striking out 38 and allowing a mere 19 runners.

13. Andrew Benintendi, 2022. Just kidding.

13. Johnny Damon, 2002

With only a year left of club control, the Royals dealt the young Damon to Oakland as part of a three-team deal that netted future American League Rookie of the Year, Angel Berroa. Totally worth it! Damon had finished 19th in MVP voting in 2001 after leading the American League in runs (136) and stolen bases (46), but this was still the dark days of Kansas City baseball, much worse than what’s going on now. There was no plan for him, or his fellow All-Star outfielders, and all three eventually departed. Damon would go on to reach two All-Star teams and win two World Series championships.

12. David Cone, 1987 & 1994

The player so nice the Royals traded him twice. A Kansas City kid, the Royals drafted Cone out of Rockhurst High School in 1981 only to trade him to the Mets after 11 outings in 1986. He later returned to the Royals in (gasp) free agency before the 1993 season. He won the Cy Young in the strike-shortened 1994 season. After the strike, again the Royals moved him, this time to Toronto for three players, two of whom never played in the majors and the other who spent a grand total of 58 games in Kansas City.

Did the Royals trade Cone that second time just after the player’s strike because he was an MLBPA player rep? [Insert shrug emoji.] Regardless, after leaving Kansas City a second time, Cone would win four more World Series (he also won one in 1992 with Toronto) and pitched a perfect game in 1999.

11. Bret Saberhagen, 1992

Now it starts hurting. Saberhagen won two Cy Young Awards for the Royals, in 1985 and 1989, and also captured World Series MVP honors in 1985 against the Cardinals. During his career in Kansas City, he had this weird tendency to perform well in only odd-numbered years. His 1989 season was one of the best ever by a Royals pitcher, and he probably should’ve won the MVP that season, but instead finished 8th. The Royals dealt him to the Mets before 1992.

10. Dan Quisenberry, 1988

Say it with me: Quiz belongs in Cooperstown! Especially when compared to other closers from his era who are in the Hall of Fame. But I digress. Quiz was a superb closer from 1980-1985, finishing top five in the Cy Young Award five times, top 10 in the MVP four times, and winning the Rolaids Relief Man Award five times. He also led the league in saves five times in those years. He lost the closer’s role in 1986, and in 1988, after being released midseason, signed with his former manager Whitey Herzog, now at the helm of the Cardinals. He also pitched five games for the Giants. I don’t know about you, but it just feels wrong that Dan Quisenberry pitched for any other team than the Royals.

9. Carlos Beltran, 2004

The Royals’ second-round pick in 1995, Beltran won the 1999 Rookie of the Year Award in a landslide and followed that up with another four-and-a-half excellent seasons. At the 2004 trade deadline, however, after being unable to reach an extension, the Royals moved him to Houston as part of three-team deal that netted the Royals three guys, including Mark Teahen and John Buck. Beltran continued playing through the 2017 season, when he won a World Series title with the Astros (he’d played with five other teams between his Houston stints). He should make the Hall of Fame, and that’ll be a tough day for Royals fans, considering the heights he reached after his trade.

8. Billy Butler, 2015

While researching this list, I checked in with some fellow Royals fans, and I was surprised that Butler’s name didn’t come up more. I feel he warrants this high on the list because he starred for the Royals from his debut in 2007 through the saddest on-field moment in Royals history, when the team dropped Game 7 of the 2014 World Series to the Giants. Then he moved on in free agency only to see the Royals win it all in 2015. In the most classic sense of the word, that’s tragic. I wish he could’ve been part of that team. Instead, he finished his career in relative obscurity with the A’s and Yankees.

7. Bo Jackson, 1991

Man, what an exciting player. And he’s got a wild story, too. A two-sport star, Jackson reached the majors in 1986 and was purely electrifying. He had a cannon for an arm and a club for a bat. He made exciting plays in the outfield and was a threat to launch the ball to Mars every time he came up to bat. In 1989, despite leading the majors in strikeouts with 172 (Joey Gallo had that at the end of this May, I think), Jackson finished 10th in MVP voting after slashing .256/.310/.495 with 32 homers, 105 RBIs, 86 runs scored, 26/35 in stolen bases. The following season, all of his numbers shot up with his OPS rising 61 points.

But Bo also played football—and not just that, he played running back for the L.A. Raiders. And on January 13, 1991, in a playoff game against the Bengals, Bo broke fractured and dislocated his hip on a pretty normal looking tackle.

On the diamond, Jackson never played for the Royals again, getting released before the 1991 season began. He latched on with the White Sox but only played in 23 games. He missed all of 1992 before playing two more truncated seasons for Chicago and California. It’s a testament to his skill and resolve that, after the hip injury, he still managed to 32 home runs.

Bo Jackson’s the biggest What If? in sports, and, therefore, in Royals history.

6. Lorenzo Cain, 2018

After the conclusion of the 2017, it became apparent Cain’s time in Kansas City had closed. Well, it became apparent before that, when he signed an extension with the Royals after 2015 but for only two years. When he hit the open market, the Royals weren’t in it, and he returned to the Brewers, the team that drafted him.

This list is, of course, subjective, but not purely so. As stated before, I reached out to plenty of other Royals fans to get their feedback. Were it just down to me, Cain would be No. 1. The man’s pure joy for the game radiated every single time the camera found him, which means that he radiated that pure joy when he didn’t know he was on camera. The dude loved the game.

Fine, if you want some numbers, he was arguably the most important player on the 2015 World Series team, finishing third in MVP voting while accumulating 7.0 WAR and earning his first (of two) All-Star berths. He scored 101 runs that season, by far his career high, while slashing .307/.361/.477 with 34 doubles, six triples, 16 home runs, and 72 RBIs. He also swiped 26 bases while playing excellent center field.

Sadly, he’s now out of baseball.

5. Mike Moustakas, 2018

When I brought up this list with two of my most trusted confidants—my wife and my duckologist—they answered without hesitation: “Moose.”

Moustakas took a while to get going with the Royals, even getting sent down to the minors for a spell in 2014. When he returned, he helped lead the team that drafted him No. 2 overall in 2007 to the brink of a world championship. He then had his best playoff series the following year against the Mets when the Royals finally captured their elusive second title.

His numbers in Kansas City weren’t great—only a 98 OPS+, two percent below league average—but he made two All-Star Games, set the club’s record for home runs in a single season (since twice broken), and stuck around longer than the other core players from 2014 & 2015.

4. Mike Sweeney, 2008

Sweeney played great baseball for a franchise that only once finished with a winning record during his 13 seasons there, and that came sandwiched in between four seasons of at least 100 losses. Still, Sweeney played well, earning an All-Star spot in five of six seasons between 2000 and 2005. For his career in Kansas City, he hit .299/.369/.492 for an OPS+ of 120. In that span, he corked 197 home runs while driving in 837 and scoring exactly 700 times.

The former 10th-round pick gave his all to the Royals, and was mostly a lone bright spot for abysmal teams. He only played in 134 games over his last two Royals seasons, and he didn’t play much more after leaving. Like Quiz, it’s odd to think that Sweeney played for other teams than the Royals. He feels like a lifer.

3. Zack Greinke, 2011

In 2009, Greinke pitched perhaps the greatest season in Royals history, winning the Cy Young Award as he went 16-8 with a 2.16 ERA (205 ERA+), 2.33 FIP, 1.073 ERA, and 242 strikeouts versus just 51 walks. He also tossed six complete games, three of them shutouts.

The Royals finished 65-97.

After the 2010 season, the Royals made a gut-wrenching decision to trade Greinke to the Brewers. But the front office’s hands were tied: Greinke wanted out, and the Royals were still years away from competing. Thankfully, the trade actually worked, as the Royals received Cain, Alcides Esobar, Jeremy Jeffress, and Jake Odorizzi.

Greinke, meanwhile, made a ton of money while cementing his Hall of Fame status while pitching for the Brewers, Angels, Dodgers, Diamondbacks, and Astros before returning to the Royals this season. Along with Beltran, Greinke is one of two future Hall of Famers traded by the Royals.

Strangely enough, the Royals have won more World Series than Greinke (1-0) due in large part to trading him.

Baseball gonna baseball.

2. Kevin Appier, 1999

Baseball-Reference.com has a neat section at the top of each team’s specific page—the team’s All-Time Top 24 Players by WAR with that team. Behind only George Brett is Kevin Appier, with 47.0 WAR.

Appier debuted with the Royals in 1989 as a 21-year-old. The following season, he finished third in Rookie of the Year voting to Sandy Alomar, but should’ve won it as he was worth almost three more wins than the young Cleveland catcher. He also definitely should’ve won the Cy Young Award (and maybe even the MVP) in 1993 but instead finished third behind Jack McDowell and Randy Johnson. It’s tough to fathom, but Appier made only one All-Star team in his career, in 1995.

Like a lot of the guys on this list, Appier played for some truly awful Royals teams. And yet, except for his cup of coffee in 1989, 1997 and 1998 (in which he pitched only three games), Appier never finished with a losing record. Overall, he finished his tenure with the Royals with a 115-92 record, 3.49 ERA (130 ERA+), 3,49 FIP, and 1.25 WHIP while striking out just under 1,500 batters.

The Royals traded him to—surprise!—Oakland for three guys who did next to nothing. Thankfully for Appier, who also pitched for the Mets and wrapped up his career back in Kansas City, he won the 2002 World Series with the Anaheim Angels.

1. Eric Hosmer, 2018

Hosmer, the leader and MVP of the 2015 World Series team, made one All-Star team and earned one Silver Slugger and four Gold Gloves with the Royals before signing a rich deal with the Padres after the 2017 season. Drafted with the No. 3 pick in the 2008 draft, his arrival to the majors in 2011 signaled that the Royals were finally ready to compete.

And with Hosmer, compete they did, suffering losing seasons only in his first two seasons with the team, reaching the World Series in 2014 and capturing it in 2015. Even those teams in 2016 and 2017 had a fighting chance for a playoff spot, despite falling short.

Hosmer was the face of franchise in those golden years, hitting big home runs, playing stellar first base, and scoring perhaps the biggest run in the organization’s history on a heads-up play.

Now with the Red Sox after four-and-a-half years in San Diego, Hosmer recently returned to Kansas City for the first time, and fans let him know just how much he still means to them.