The job of a Major League Baseball general manager is a relentless, 24/7 commitment that extends far beyond the ballpark, encompassing everything from births to funerals. This is never more true than in the weeks leading up to the July 31 trade deadline, when a single missed call or text can mean a lost opportunity.
MLB executives recently shared some of their most memorable stories about making deals at the most challenging and inopportune times.
Trade Talks at Life’s Extremes
Before becoming president of the Dodgers, Andrew Friedman ran baseball operations for the Tampa Bay Rays, where Milwaukee Brewers general manager Matt Arnold served as his assistant. Arnold recalls two separate trade deadlines when Friedman was unexpectedly hospitalized.
“One year his appendix almost burst,” Arnold said. “He was doubled over in pain, and we had to have a doctor come to the stadium.”
Friedman was rushed to the hospital for appendicitis treatment, leaving his staff to manage deadline negotiations while he drifted in and out of consciousness. “We spent July 31 at the hospital with him medicated,” Arnold recalled. “We were trying to piece together conversations we’d had with him. B.J. Upton was involved, but I don’t think we ended up trading him.”
As chaotic as that was, Arnold believes the following year was even more remarkable. “His wife had a baby on the trade deadline,” Arnold said. With the team in the middle of multiple trade scenarios, the staff was texting Friedman throughout the labor. “We went back and looked at the timestamps of when he had sent texts and when the baby was born. It was minutes apart,” Arnold said. “He told us she was kind of propped up, and he was texting about the trade from behind her head. We were like, ‘Welcome to the world, Zach Friedman.'”
White Sox general manager Chris Getz experienced a similarly challenging moment when his uncle passed away. Getz, a pallbearer at the funeral, found his work life encroaching on the solemn day. “There’s a GM out there who if there is interest, he doesn’t stop calling,” Getz said. “I told him, ‘My uncle passed away, and I have his funeral, but don’t worry, we’re going to do the deal… I just need a couple of hours.’ He says, ‘Cool, I got you.'”
The calls, however, did not stop. “My phone is ringing at the funeral now,” Getz said. “It wasn’t actually ringing when I was carrying the casket, but it was close enough. I told people at the celebration afterward what was going on, and they were like, ‘Hey Chris, Uncle Mike would have absolutely loved that you executed a trade at his funeral.'”
San Francisco Giants GM Zack Minasian had a similar experience last January after his grandmother’s death. “I had to find us $500,000 of international money,” Minasian said. “I’m literally going from the church to the graveyard, on the phone trying to get us $500,000. It’s the same church my grandmother got married in. I had my brother [Angels GM Perry Minasian] next to me driving so I could text.” He eventually secured the funds by trading Blake Sabol to the Red Sox and Will Kempner to the Marlins. When asked why he didn’t just ask his brother, who was sitting beside him, Minasian laughed. “Shocker. He didn’t have it!”
Another executive, speaking anonymously, recalled negotiating a minor deal during a Passover seder at his in-laws’ temple. “I’m feeling the texts coming through in my pocket,” he said. After excusing himself once to use the restroom and advance the talks, he needed another opportunity. “I was trying to be respectful, not checking the phone,” he said. “But at one point, one of my kids needed to go to the bathroom and my hand shot up. I said, ‘I’ll take him.’ I ran out in the hall… and real quick called the other team to get the ball rolling. We got the deal done.”
Communication Breakdowns
A few days before Christmas in 2022, Arizona Diamondbacks GM Mike Hazen was on a family vacation in Hawaii while finalizing a major trade sending Daulton Varsho to the Blue Jays for Gabriel Moreno and Lourdes Gurriel Jr.
“I finalized the deal with [Blue Jays GM] Ross [Atkins] right before we were supposed to go zip-lining,” Hazen said. “We are driving to the middle of nowhere in Maui, and I knew I was going to lose cell service.” Hazen managed to reach Varsho just before his phone signal died but still needed to contact his new players. Upon arriving at the zip-lining location, he discovered the Wi-Fi was down. “I drop the kids off and tell them I’ll be back when I can, and I drive back to the closest town so I could get cell service,” Hazen said. He sat at a restaurant, made the calls, and returned to find his kids midway through their adventure. “They didn’t mind,” he said. “At least, I don’t think so.”
Cubs president Jed Hoyer, then a young executive under Theo Epstein with the Boston Red Sox, remembers the chaotic 2004 trade deadline. While Epstein was finalizing the blockbuster four-team trade involving Nomar Garciaparra, he was also trying to acquire Dave Roberts from the Dodgers.
“Theo was trying to finish the Nomar deal on an old-school phone,” Hoyer recalled. “At one point, he whipped the phone to me and said, ‘Finish the Roberts deal.’ But I couldn’t understand [Dodgers GM] Paul DePodesta on the phone. It was a choppy connection.” After he hung up, Epstein asked if the deal was done. “I just looked at him and said, ‘I think so?’ with a shrug,” Hoyer said. The trade, of course, led to Roberts’ famous stolen base and a curse-breaking title for Boston. “And now he might be a Hall of Fame manager,” Hoyer added. “Glad it worked out.”
In July 2009, St. Louis Cardinals executive John Mozeliak’s golf outing was interrupted by trade talks with Athletics GM Billy Beane for slugger Matt Holliday. “All of a sudden the skies open up, it’s pouring, and I can’t hear on my cell phone,” Mozeliak said. He abandoned his round after three holes and retreated to his car to escape the rain and conduct business away from the prying eyes of a private country club where cell phone use was prohibited. “I’m sitting in my car getting pelted by small hailstones,” he said. The negotiations continued through a family dinner at a local pizzeria. “By the time that dinner ended, we had a deal and we got Matt Holliday.”
When Chaos Reigns
Cubs GM Carter Hawkins, then an assistant in Cleveland’s front office in 2012, was part of a trade to send Drew Pomeranz and others to Colorado for Ubaldo Jimenez. Hawkins was dispatched to the team’s Double-A affiliate in Akron to inform the players.
“Pomeranz was starting. We had to go get him out of the bullpen and tell him,” Hawkins said. But a miscommunication meant Jimenez was still pitching for the Rockies, so the trade was on hold. “We brought them all back in to tell them they weren’t being traded.” Shortly after, Jimenez was pulled, and the deal was back on. “So we brought all the guys back in to tell them they were being traded,” Hawkins continued. “Then we realize it had not been a calendar year since the day Pomeranz had signed, which was a rule. You could not trade a drafted player within that first year. So now we had to tell Drew he was going to be traded—but not for two weeks. By that time, his head was spinning.”
Jim Duquette, former co-GM of the Baltimore Orioles, recalled the painstaking work he and Mike Flanagan did in 2006 to trade slugger Miguel Tejada. After getting ownership’s permission, they spent 16-hour days narrowing offers from the Mets, Astros, and Angels. They settled on a significant package from the Angels that could have included Bartolo Colon, Erick Aybar, or Ervin Santana.
“It would have changed our organization,” Duquette said. They marched into owner Peter Angelos’s law office with a whiteboard for an elaborate presentation. “We sat there for 30 minutes going through all the options,” Duquette explained. “At the end of it, he pauses, looks up at us both and all he said was, ‘No, I don’t want to trade him.’ No reason. Just ‘No!'”
The Aftermath: Successes and Regrets
In 2012, his first full year as GM of the Los Angeles Angels, Jerry Dipoto needed to fix a struggling bullpen. “May is a difficult time to make any meaningful trades,” Dipoto said. Still, he acquired reliever Ernesto Frieri from the Padres for two prospects. “He was like a 1.5-pitch type of reliever… fourth or fifth on the Pads’ depth chart,” Dipoto said.
Frieri made an immediate impact. “He played catch down the line the first day and our pitching coach was like, ‘Wow, you can’t pick up this guy’s ball at all,'” Dipoto recalled. “He threw a scoreless inning that night and the next night he was closing.” Frieri started his Angels career with 20 scoreless innings. “We didn’t know we were getting a star.”
Dipoto, now with the Mariners, had another memorable dealing with the Padres during the 2020 season. San Diego was aggressively pursuing catcher Austin Nola. “We were in full rebuild mode but didn’t have much interest in moving him,” Dipoto said. But Padres GM A.J. Preller was insistent. “He threw out a slew of names and said, ‘We will overpay,'” Dipoto recalled. The Mariners received four players, including Ty France.
Later, with just minutes until the deadline, the Padres called back, wanting reliever Taylor Williams. In return, the Mariners asked for Matt Brash, a prospect with just one inning of minor league experience. “We were so close to the deadline that I heard A.J. cup the phone and yell, ‘BRASH?’ to one of his assistants,” Dipoto said. “Then he gets back on and says, ‘We’ll do it.’ It’s the only deal I’ve ever done without seeing the medicals. There was no time. But Brash has been good for us.”
Sometimes, a deal that falls apart proves to be a blessing. In 2018, Mike Hazen’s Diamondbacks were competing with the Dodgers to acquire Manny Machado from the Orioles. “We tried to get Manny Machado… and Jazz Chisholm would have been in that trade,” Hazen said. The Dodgers ultimately landed Machado. But because the Diamondbacks held onto Chisholm, they were able to trade him a year later for a young pitcher named Zac Gallen, a cornerstone of their 2023 World Series team. “We don’t get Gallen if we make that trade for Machado,” Hazen noted, “so you never know.”
Zack Minasian recalled a near-miss during his time with the Brewers when the team was in deep discussions with the Mariners, then run by former Brewers executive Jack Zduriencik. “Jack and Doug [Melvin] were talking about a trade that would have sent Felix Hernandez to Milwaukee,” Minasian said. “At one point, we thought Jack had agreed to it but he needed to make one other move before we could finalize it. It didn’t happen, but for an hour we thought we were getting Felix Hernandez. We were nervous, anxious, excited, and just waiting.”
