‘You’re Not Screwing Me on This One, Are You?’: Big League GMs Reflect on Their First Trades

[Padres]

by Zach Buchanan (Fangraphs)
March 14, 2024

For one awkward beat, there was silence.

Just like always, everyone in the room had offered an opinion. The December 2022 move the Royals were discussing was hardly a blockbuster – right-handed reliever Wyatt Mills to the Red Sox for relief prospect Jacob Wallace – but the process leading up to it was still time-tested and thorough. One by one, members of the Kansas City brain trust chimed in with their thoughts. Then, they turned toward Royals general manager J.J. Picollo.

Three months earlier, with the previous season winding down, the Royals had dismissed longtime GM Dayton Moore and elevated Picollo after years as Moore’s top deputy. Small as it was, the Mills-Wallace deal was to be the first of his administration. He’d been in that room for countless trade discussions and he’d listened as each department in baseball operations weighed in. Except now, the final say was his and his alone.

So long as he remembered.

“I sat there after I got everyone’s opinion,” Picollo recalls, “and somebody actually said, ‘You’ve got to make the call now.’”

Stay in the position long enough and any GM will add a litany of trades to their ledger – Mariners executive Jerry Dipoto knows his tally is well over a hundred – but there’s always something about the first. Diamondbacks GM Mike Hazen looks back at his first deal seven years ago and sees naïveté. “I was blindly dumb and optimistic,” he says. Others vividly recall pressure and gnawing uncertainty – the feeling of a rock left uncovered, an angle unconsidered. To make any trade is to venture onto a limb knowing that if it cracks, it will be your bones that break in the fall. “It’s exciting and terrifying all at the same time,” says Angels GM Perry Minasian. If you won’t take a risk, if you’re unwilling to bat a flirtatious eye at danger, then swinging trades just isn’t for you.

“There is a rush that you get,” says Dipoto, “when you’re about to push that button.”

Few GMs have traded as prolifically as the 55-year-old Dipoto, and his first trades were characteristically bold. Dipoto was just the interim GM with the Diamondbacks when he executed a series of trades that reshaped the franchise at the 2010 deadline. First, he dealt ace Dan Haren to the Angels for a package that included Joe Saunders, Tyler Skaggs and Patrick Corbin. Soon after, he landed Daniel Hudson from the White Sox for Edwin Jackson. The flurry ended at the deadline when he shipped catcher Chris Snyder to the Pirates.

He’d been on the job a month, and though Diamondbacks owner Ken Kendrick had given Dipoto his blessing to make big moves, there was no guarantee he’d remain in the position. (Indeed, the Diamondbacks hired Kevin Towers as GM before the end of the season.) And though it’s hard to imagine now, at that point he lacked significant experience in trade talks even as an underling. So, amid the frenzy, Dipoto sought the counsel of a peer. Alex Anthopoulos had risen to Blue Jays GM after the firing of J.P. Ricciardi a year earlier, and Dipoto frequently picked his friend’s brain to ensure nothing was wrong with his own.

“When you have a strong relationship and you know they’re not playing in the same pond you’re playing [in], I have no problem calling and just bouncing an idea off someone. ‘Am I crazy for thinking this?’” Dipoto says.

It’s good to have sounding boards, but relying on them too much can be perilous. Padres GM A.J. Preller executed a similar trade spree when he was first hired in San Diego, acquiring Matt Kemp, Justin Upton, Wil Myers and Derek Norris in four separate deals in December of 2014. The effort to quickly build a contender infamously flopped. “The decisions I made,” Preller says, “were not very good.”

A big reason why, he thinks, was that he was new to the organization. He didn’t know the players he’d inherited, nor the evaluators and their tendencies. Like Dipoto, he leaned on friends and mentors around the game, only to a fault. After the missteps of his first season, Preller learned to value the collective wisdom in his department far more than whatever expertise he could source elsewhere.

“Outside voices and other relationships I’ve had in the past, they probably don’t do me any good,” Preller says. “It doesn’t mean I think less of those relationships or those people’s abilities and how they see the game, but that doesn’t really impact the Padres.”

Stepping into any GM role for the first time can be daunting, but taking over a new organization can be especially tricky. GMs who are promoted from within can bank on their familiarity with the team and their evaluators, and have usually spent years participating in trade discussions. But helming a new team means a crash course in learning the org and fielding probing inquiries from the heads of 29 other clubs. Sometimes, says Brewers GM Matt Arnold, a new GM might be more willing to part with players they didn’t personally acquire. “Maybe they’re a little more willing to talk about guys who came from the ‘old regime,’” Arnold says. At the very least, new GMs often bring new organizational priorities, sending potential trade partners on a fact-finding mission.

Just last month, the Royals acquired reliever John Schreiber from the Red Sox. Even in his short time as GM in Kansas City, Picollo has executed several swaps with Boston, but he had always dealt with former baseball ops head Chaim Bloom. When the Red Sox replaced Bloom with Craig Breslow this winter, whatever read the Royals had on Boston’s preferences went out the window. Picollo and Bloom could work out deals in shorthand based on past discussions. Picollo and Breslow had to start from scratch.

“It was very new-man-in-town. The processes maybe haven’t changed a whole lot just yet, but the names that were [at] one time interesting to the Red Sox weren’t interesting in this context,” Picollo says. “We tried that avenue and it didn’t work.”

The information vacuum is far greater when you’re the new GM in a new organization. When Anthopoulos got the top job in Toronto, he threw himself into the deep end by trading franchise icon Roy Halladay to the Phillies before the 2010 season. That decision may have been emotionally fraught, but it was also strategically obvious. Halladay had a year left on his contract and was politely demanding a trade to Philadelphia. His contract allowed him to block a deal to any other club. (“I’ve never given out a no-trade clause since,” Anthopoulos notes.) That hurt Toronto’s leverage but also streamlined the club’s thinking. The Blue Jays could keep Halladay against his wishes, play a non-competitive season and receive draft pick compensation when he hit free agency, or they could do right by him and get the best players they could immediately. The decision made itself.

But in 2017 when Anthopoulos landed the Braves GM job, he found himself much more unsure. For advice, he called two colleagues, Hazen and Pirates GM Neal Huntington, both of whom had taken over new teams after years spent in other organizations. A piece of advice from Hazen especially resonated. Don’t be in a rush to trade your prospects, the Diamondbacks GM told Anthopoulos. You don’t know what they are yet.

Hazen spoke from experience. His first trade in Arizona was to acquire Taijuan Walker and Ketel Marte from the Mariners, a deal that has undeniably worked out in his favor. But Hazen also made a rookie GM mistake. He didn’t know enough about minor league outfielder Mitch Haniger, one of the players he was sending back to Seattle. “We didn’t evaluate Haniger properly,” Hazen says. “We were too quick to put Haniger into the deal, for sure.”

Haniger had cracked the majors the previous season and posted a .713 OPS, but he’d also undergone a swing change that would fuel a breakout in Seattle. Hazen and his new front office were too new to the organization to know that. The Mariners, Dipoto admits, “were trying to slip one under the radar,” although the Seattle GM says his Arizona counterpart kept his guard higher than Hazen lets on. “I remember him saying to me, ‘You’re not screwing me on this one, are you?’” Dipoto says with a laugh. “I said, ‘No, the trades don’t screw you. The free agents do.’” To account for the nagging uncertainty about Haniger, Hazen asked that Marte be included in the deal.

“You have to enter into the discussion like you’re the dumbest guy in the room,” Hazen says. “[Otherwise], that’s when you’re going to get taken to the cleaners.”

If there’s a common trait among the game’s top dealmakers – aside from a direct and no-nonsense manner, which many GMs say is a big reason Dipoto pulls off so many trades – it’s a willingness to be wrong. Not to court unnecessary risk, but to make peace with an inevitable amount of it. In that vein, a few pieces of advice he received early in his career have stuck with Anthopoulos. Kenny Williams told him to never trade “the SportsCenter guys,” but two other experienced GMs encouraged boldness. Billy Beane said to not fear trading away a good player. Pat Gillick warned him to never lose his nerve.

“Two or three years later, I made some mistakes and I knew why and it was I lost my nerve. I took my hands off the steering wheel and I handed it over. I got gun shy,” Anthopoulos says. “And I thought of Pat Gillick after the fact.”

No one would accuse Anthopoulos of being gun shy now – nor Hazen and especially not Dipoto. When Dipoto was handed the reins in Arizona a month before the trade deadline, he could not have known that his career would become synonymous with making trades. He’s such a trade junkie that, unsatisfied with the innumerable deals he’s made already, he even keeps a running spreadsheet of moves he might make. But to that point in his career, he’d been a scout. Then he traded Dan Haren in a deadline flurry and took his first steps into a wider world.

“I loved the thrill,” he says.

To make good trades, you better.

[Guardians]

I read this earlier and thought it was a really fun article.