How MLB teams orchestrate three-way trades: The hidden framework behind baseball’s most complex swaps

Matt Arnold, general manager of the Milwaukee Brewers, keeps a whiteboard in his office closet where he sketches trade scenarios. The more complex the structure, the more it appeals to him. His appetite for intricate deals traces back to lessons learned under Andrew Friedman at the Tampa Bay Rays, where he studied how to satisfy the "give" and "get" for all sides of a transaction.

Three-team trades exist because two-team negotiations often stall. When the Milwaukee Brewers and Oakland Athletics were discussing prospects in late 2022, the talks died. But when the Braves began pursuing Athletics catcher Sean Murphy, Arnold spotted an opening: the Brewers wanted William Contreras, the catcher losing playing time to Murphy. A third team made the deal possible.

A.J. Preller, president of baseball operations for the San Diego Padres and one of MLB's most active traders, frames the problem simply: "Adding a satisfied third party is even harder" than aligning two teams on value. "It's almost like you're going to dinner with a bunch of people, and someone's got to throw in a little extra money to pay the bill," said Alex Anthopoulos, the Braves' president of baseball operations.

The structural challenge is real. One side frequently feels shortchanged. The other two teams must decide whether to add more value to close the deal. Billy Beane, the Athletics executive famous for "Moneyball," calls these tangled arrangements "hairballs"—frameworks so convoluted you regret proposing them.

Three-team trades account for roughly 1.5 percent of all MLB trades over the past five seasons, ranging from one to four deals per year. The Tampa Bay Rays have engineered five of the past six three-team trades, a dominance that reflects their front office philosophy. Erik Neander, the Rays' president of baseball operations, emphasizes transparency over gamesmanship. "The Rays are not only going to be creative and open-minded," Pittsburgh Pirates GM Ben Cherington said, "but they're going to be pretty honest about how they're valuing players."

In December, Cherington was seeking lineup upgrades while the Rays held second baseman Brandon Lowe. The Houston Astros wanted controllable starting pitching but had no interest in trading big-league position players. Neander recognized the three-way fit. "It pretty quickly turned into, maybe this is easier if we involve all three," Cherington recalled. A couple of calls later, a three-way text thread was established, and the six-player trade satisfied each team's roster needs.

The anatomy of a three-team trade depends on prerequisites: the right players must be available, GMs must understand the market intimately, and trust must exist that introducing a third party won't antagonize your original trade partner. One anonymous executive summed up the toll: "I hate doing three-team deals. They're such a pain in the ass."

Unlike the NBA, where salary-cap restrictions force third teams to balance money (and three-team trades are common), or the NFL (where they rarely happen), MLB operates without mandatory salary-matching. This freedom allows three-team deals to benefit all sides meaningfully. Often one team prioritizes future value—targeting prospects—and because most MLB draft picks are not tradeable, farm systems become the currency bridging the gap.

Repeat players dominate three-team deal brokers. Many of the GMs involved have worked together before and trust each other to handle complex negotiations. Arnold's willingness to insert himself into deals, Neander's commitment to transparency, and Preller's experience create a web of relationships that enables these deals to happen at all.

When talks stall at the two-team stage, executives keep their phones close and their eyes on laptops or whiteboards until trade deadlines arrive. The persistence required is real: most three-team concepts never materialize. But for those GMs willing to invest the energy—and for the teams that benefit from creative brokering—the reward is a roster shaped by complexity that two simpler negotiations could never achieve.