Sometimes it’s an exit you see coming as the July 31 trade deadline approaches. Other times, the news comes out of nowhere in the middle of the off-season. During this calm before the storm of winter transactions, we decided to ask our contributors about the player exits that left them the most heartbroken.

Dan R Epstein: I’m a Yankee fan. We are the heartbreakers, not the heartbroken.

Mike Carlucci: It was July 31, 2004 and I was on vacation with my family in California. As we drove up the coast we were listening to the radio report deadline deals. Eventually there was a gap between stations as the road entered less populated areas but the deadline had passed – the Red Sox hadn’t done anything crazy. Until I got a voicemail notification – no service. But then one bar came up and I listened to my uncle saying the Red Sox had traded Nomar.

Nomar!?!?! How could they trade Nomar? It had to be a joke. We listened to static and silence as the car continued to drive through a radio dead zone. And then we were back. Orlando Cabrera was replacing him? Doug Mientkiewicz? What happened to Millar? (He was fine.) The news was shocking. None of us could believe it. But it happened.

I kept rooting for Nomar. I have one jersey, Nomar’s. We were both born on July 23rd. I’m sure he was lots of people’s favorite player but how many also shared the 23rd? I was watching the Cubs game by chance where baseball witnessed the painful fall. He had a few more good seasons in Oakland and LA but it was never really the same as his first few years in Boston. No trade deadline will ever match that one–not just in terms of shock and the lack of Twitter or internet-enabled phones, but the way the Red Sox played from there right through the magical World Series.

Scott Kramer: The Cubs let Maddux walk after the 1992 season.

I immediately became a Rockies fan.

Barry Gilpin: As a kid, Eric Davis was my favorite ballplayer. The speed, the power, and–until his legs started to go–the defense. This guy was the total package, and I don’t mean Lex Luger. In 1991, Davis had struggled a bit, but was still a league average hitter or thereabouts. I was in Kentucky visiting my grandmother for a few days and went to visit my cousin when his newspaper came. (Remember those?) So, we are outside shooting hoops when his dad walked by and said something I couldn’t hear. I’m assuming he was complaining about the trade. After his father had left, in typical 13-year-old boy fashion, he turned to me and said, and this is exact, I remember it so clearly, so pardon the language, “Dude, they fuckin traded Davis!”

Cincinnati media had been killing Davis all year and he was getting the occasional boo, so I wasn’t surprised. But, the guy was playing right after lacerating his kidney in the World Series. Intelligent people would expect that maybe that’s a bit of a slow recovery for a sport where you are constantly rotating that part of your body, but as Facebook has taught us all, people are dumb. And honestly, the Dodgers trade worked out. Tim Belcher was worth 3.6 bWAR over the next season and a half before he too was traded, and Davis cratered. After taking a year off to heal up, we almost had a happy ending.

Davis signed a minor league deal with the Reds in 1996, and surprisingly wound up making the team and revitalizing his career. But, after posting a 140 OPS+ in 1996 and making Reds fans fall back in love with him, you know it, the Reds lowballed him the next offseason, and he bounced, and I didn’t blame him one bit. But how awesome would that have been to have him finish out his career (and beat cancer and come back to play again) in the place that he’s remembered for?

Ken Maeda: If asked who my first sports hero was, I’d be reluctant given that his name is Orel Hershiser. Unbeknownst to me at the time, he started the first game I ever attended, at Dodger Stadium in 1988, in which he only survived 2 IP. He never left early again, going at least 9 IP in nine remaining starts, with a 59-inning scoreless streak along the way. But it wasn’t until that offseason that I’d learn more about baseball and develop an appreciation for his record and the team’s championship run. I even read his autobiography.

His ’89 season was in many ways just as good, but 1990 was cut short due to a shoulder injury. The ’94 strike would end his LA tenure, as he would later sign with Cleveland as a free agent. I’m not sure how I would’ve learned the news in those days — the CNN sports ticker perhaps, or a top-of-the-hour sports radio update. It was tough, but not shocking. He got a share of the postseason spotlight a few more times, and later stayed casual during the still-hilarious “Bobby V in disguise” incident. He capped his career with a 10-game, 13-ERA season back in LA, but by then I had decided I should probably just stick with the Angels — the team we lived closer to during our time there. Now I find myself counting down the days until another old Dodger favorite (and Hershiser’s battery-mate), Mike Scioscia, will finally depart after managing for 18 years….

Scott Kushner: When Giambi left the A’s I was crushed. Not because it was such a surprise, but because it was so obviously inevitable.

When the A’s blew the 2-0 lead in the 2001 ALDS to the Yankees, I cried as game 5 came to a close. Not just because their season was over, but because the band was breaking up.

That Giambi went to the Yankees was just a perverse joke.

Mick Reinhard: When Don Mattingly became a free agent in November 1995, I thought it was just a formality the Yankees would re-sign him for another season in pinstripes. But then on December 7, Seattle traded Tino Martinez to New York to become the Yankees’ next first baseman.

Perhaps Mattingly told the Yankee brass he was going to retire so they went out and acquired his replacement. A bad back had exacerbated a downturn in his overall production and diminished his durability. But I don’t remember it like that at all. Suddenly, it was no longer Mattingly’s choice anymore. It sure felt like the front office forced his hand and pushed the Yankee captain out the door.

Even though I know Martinez was just a commodity in the exchange, that didn’t stop me from carrying a grudge against him personally for his part in the deal. He would obviously go on to become an integral piece to the Yankees’ dynasty but he never heard my cheers.

Khurram Kalim: During my early days as a Mets fan, I really enjoyed watching John Olerud play first base. Olerud wouldn’t tether himself to the bag with a runner on, which experts would say was a testament to his unique defensive ability. He’d play off the base, then dart to the bag while the pitcher’s pick-off attempt was mid-flight. He kept runners honest, yet still maximized his glove’s range. That skill belonged to my first basemen on my team who, it turned out, also happened to be my favorite player.

And then he left. Just as the Mets found success for the first time in my life, Olerud was gone, off to the Mariners in December 1999, and the pedestal I put him on tipped over. I remember wondering how a player could choose to leave a team that was just two games short of the World Series. I remember I was upset that that player was my favorite. It hurt.

But I’d always care about John Olerud. I made peace with his desire to be closer to his family. Winning the pennant in 2000 helped dull the pain. Edgardo Alfonzo ascended the player rankings, and connective contrails to Olerud cleared. Still, for the next three and a half years, while Olerud played in a land beyond print deadlines, my daily box score scan of the paper’s sports section included perusing the west coast results—usually a day behind—just to see if he was fine. In Seattle, he often was.

Mark Sands: Growing up, my favorite player was Tigers catcher Lance Parrish. I wore his number (13) in little league, dressed up as him for Halloween (twice!), and had two posters of his up in my room. I was very excited when he appeared on an episode of Diff’rent Strokes. I got to meet my baseball hero just before my 9th birthday when he visited Kalamazoo with the other Tigers during the Winter Caravan trip around the state. I even got to have my picture with him in the Kalamazoo Gazette. But after the 1986 season, I learned the hard lesson that baseball is a business.

Back then, if a player didn’t re-sign by a certain date, he could not do so until the next May. Even when that date came and went and Lance was a free agent, I just assumed he wouldn’t leave me and would later return to Detroit. But of course, that never happened. When I came home from school on a Friday in March, my parents broke the news that Parrish had signed with the Phillies. I burst into tears and, according to my mom, ran up to my room and stayed there for the whole night. I just remember thinking that it was some kind of a mistake, that he HAD to come back. Little did I know that I should’ve been mad at the notoriously cheap Tigers for trying to sign a great, all-star catcher on the cheap. Sadly, the aging curve was not kind to my 31-year-old favorite player.

Parrish amassed nearly 30 WAR in his first 9+ seasons with the Tigers. He would not get to 40. 1987 was his worst year as a starter, hitting just .245/.313/.399 with 0.4 WAR. I blamed Philly and the stupid NL for his poor season and irrationally hated his replacement, Matt Nokes (who was awesome for Detroit in 1987-89). Unfortunately, Lance would only have one more great season. In 1990, with the California Angels, he was his old self again, a 4.5 WAR player with a ton of power at C (24 HRs) and hitting .268/.338/.451.

Parrish is still my all-time favorite — a great defensive catcher with a cannon arm and plus power. He was also very kind to a 9-year-old kid who obviously idolized him. This winter, the Tigers announced that he’ll manage the relatively nearby West Michigan Whitecaps. Hopefully, I’ll get another picture with him, and maybe even get him to sign the one we took together in 1987.

Brandon Lee: It’s hard to console a 6-year-old and make them understand everything that goes into making a life-changing decision, especially one that puts an end to (or at least a pause to) greatness. In October 1993, Michael Jordan retired from the NBA and the Chicago Bulls. They had just won three consecutive championships and he was in the process of staking his claim to being the best of this generation. He wasn’t only my own favorite athlete – he was the world’s biggest celebrity.

As we all know, Jordan didn’t retire from sports as a whole, but instead played baseball for the White Sox at AA in ’94. I attended my first Cubs game that year. (As a 7-year old I also didn’t know much about labor disputes.) Before the game started I asked whether Jordan was going to play. To my disappointment the answer was “no” — he played for the other Chicago team, and not even really for them but in their minor leagues. That actually helped me understand the structure of the game (AL/NL, Major/minor leagues) and contributed to my tracking his progress with the Birmingham Barons through the local news in Chicago throughout the year.

Jordan would of course return to the NBA in 1995 and cement his legacy as the Greatest Of All Time (or “among the greatest” if you’re being wrong about it). The silver lining here is that Jordan switching sports for a year got my attention. It made me realize that there’s something out there other than basketball — which in turn helped me realize that there are acceptable results that aren’t “win the championship.” It made me realize that baseball is a thing — that Chicago had not one but TWO teams, including one that plays basically down the street from where I live. While I didn’t really go all-in for the game until a couple years later, it was Michael Jordan who put baseball on the map for me. Thanks for giving it a try, Mike.

Andrew Patrick: The short version is that Cespedes‘ arrival was magical as a fan of the low budget A’s. He not only correlated with an unexpected run of success for the A’s when they were supposed to be bad, but also a lot of good things in my life. I found out on the John the morning of the trade deadline. I was stunned, even as an avid hot stove follower. It was tough. (The long version can be found in this 2014 post.)