Trade Talks at the Most Inopportune Times

Brewers general manager Matt Arnold and Dodgers president Andrew Friedman have some of the most unusual trade deadline stories. Arnold recalls a time when Friedman was in the hospital with appendicitis during the trade deadline. "We spent July 31 at the hospital with him, medicated, going in and out of consciousness," Arnold said. "We're trying to piece together conversations we've had with him as he's in a lot of pain. That was pretty nuts."

Another year, Friedman was at the hospital because his wife was in labor. "We went back and looked at the time stamp of when he had sent texts and when the baby was born," Arnold said with a laugh. "It was minutes apart. So we asked him what was going on in there?"

Trades During Funerals

White Sox general manager Chris Getz had to navigate a trade during his uncle's funeral. "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 afterwards what was going on and they were like 'Hey Chris, Uncle Mike would have absolutely loved that you executed a trade at his funeral.'"

New San Francisco Giants GM Zack Minasian had a similar experience after his grandmother's funeral. "I'm literally going from the church to the graveyard, on the phone trying to get us $500,000," Minasian said. "It was not my best day."

Communication Issues

Arizona Diamondbacks GM Mike Hazen found himself in a tough spot during a family vacation in Hawaii. "I was trying to finalize the Daulton Varsho/Gabriel Moreno/Lourdes Gurriel trade [with the Blue Jays]," Hazen said. "I knew I was going to lose cell service. We have a time slot for the zip lining we have to get to. I had my oldest kid driving and I was trying to get a hold of Varsho to tell him about the trade and I couldn't."

When Chaos Reigns

Cubs president Jed Hoyer recalls a chaotic trade deadline in 2004 when he was with the Boston Red Sox. "Theo was trying to finish the Nomar deal on like an old-school phone," Hoyer said. "At one point, he whipped the phone to me and he said, 'Finish the Roberts deal.' But I couldn't understand [Dodgers GM] Paul DePodesta on the phone. It was a choppy connection."

When the Trade Goes Through -- for Better or Worse

Jerry Dipoto, known as "Trader Jerry," has some memorable trade stories. In 2012, he acquired Ernesto Frieri from the Padres. "We didn't know we were getting a star," Dipoto said. "He threw a scoreless inning that night and the next night he was closing."

When the Deal Falls Apart

Zack Minasian recalls a time when the Brewers thought they had a deal for Felix Hernandez. "For an hour we thought we were getting Felix Hernandez," Minasian said. "We were nervous, anxious, excited and just waiting."

The Ripple Effects of a Failed Trade

Mike Hazen remembers a trade that fell through but ultimately benefited the Diamondbacks. "We tried to get Manny Machado from the Orioles in 2018 and Jazz Chisolm would have been in that trade," Hazen said. "We didn't trade Jazz there but that got us Zac Gallen in 2019. We don't get Gallen if we make that trade for Machado, so you never know."