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Matt Arnold, the general manager and president of baseball operations for the Milwaukee Brewers, keeps in his office closet a whiteboard on which he sketches his zaniest trade concoctions.
The more complex, the more hes tickled by the daunting premise.
Arnold has been building rosters since he was a kid studying Street & Smith magazines, scribbling scrupulous notes and then tagging along for his dads workplace fantasy baseball drafts.
While working under Andrew Friedman in the innovation hub that is the Tampa Bay Rays front office, Arnold learned the value of satisfying the give and get for all sides to push a trade to the finish line.
The deals they pulled off and the many that fizzled are on the whiteboard somewhere, Arnold said.
Advertisement With trade season at hand, executives will keep a death grip on their phones and their eyes glued to laptops (or whiteboards) until 6 p.m.
Eastern Time on Aug.
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Theyll try to find a partner to align on a surplus-for-deficit deal, or an exchange of a veteran for prospects.
Many conversations will ultimately plow into dead ends.
Yet some stalled talks, with a little creativity and courage, can be revived by bringing in another party to facilitate the deal.
In most cases, a three-team trade is the product of a failed two-team trade and bullheaded persistence.
Its hard getting two teams to agree on fair value, said Major League Baseballs most notorious wheeler and dealer, San Diego Padres president of baseball operations A.J.
Preller.
Adding a satisfied third party is even harder.
One side tends to feel shortchanged, and the other two have to decide whether to kick in more value to save the deal.
Its almost like youre going to dinner with a bunch of people, and someones got to throw in a little extra money to pay the bill, said Atlanta Braves president of baseball operations Alex Anthopoulos.
In recent months, The Athletic canvassed MLB general managers and presidents of baseball operations to dissect the anatomy of a three-team trade.
Its a delicate and frequently fruitless dance.
I hate doing three-team deals, one exec grumbled.
Theyre such a pain in the ass.
They require the right players, an intimate knowledge of the market, and trust that introducing a third team wont irk your original trade partner, and that the other two teams wont run off together and leave you alone at the altar.
Billy Beane, the Athletics exec of Moneyball fame, coined these complicated deals hairballs.
The framework of the trade can grow so gnarly and convoluted that you wish you had never brought it up.
One such hairball started innocuously after Arnold took over as the Brewers chief decision-maker in October 2022.
The then-Oakland Athletics expressed interest in speedy Brewers outfield prospect Esteury Ruiz.
Those talks, like most, went nowhere.
The teams werent a fit.
Advertisement A few weeks later, reports emerged that the Braves were working to acquire Athletics catcher Sean Murphy.
The Brewers liked the catcher set to lose playing time to Murphy: William Contreras.
Sensing the ingredients were there for a three-team trade, Arnold re-engaged the Athletics.
Each trader has a different operating style and appetite for intricate deals.
Arnold is a transaction fiend.
At the mere mention of a three-team concept, a grin spreads across his face.
I love trying to get in the middle of those things, he said.
Especially if you have a whiteboard at the Winter Meetings and youre just kind of bored and youre trying to get some stuff done, its like, Hey, lets see if we can insert ourselves in a deal.
Three-team trades arent unique to baseball.
They are far more frequent in the NBA because of its strict salary-matching rules for teams over the salary cap (which is almost all of them); a third team with cap space is brought in to balance the money.
Similar brokering is common in the NHL.
In the NFL, however, three-way deals are virtually non-existent these days, as there are fewer trades overall and more ways to create cap space.
Unencumbered by salary caps or mandatory money-matching, MLB tends to produce more three-team trades that meaningfully benefit all sides.
Often, one team is primarily focused on future value a team targeting prospects and because most MLB draft picks are not tradeable, clubs massive farm systems become the currency that can bridge the gap.
In MLB, three-team deals have accounted for roughly 1.5 percent of trades in the past five seasons, according to data from FanGraphs transaction tracker, with as few as one and as many as four three-teamers in a year.
No team has embraced the Rubiks Cube nature of the three-team trade like the Rays, who have nudged their way into five of the past six three-way swaps.
That bit of trivia surprised Rays president of baseball operations Erik Neander, but not his counterparts across the league.
Tampas front office looks to eke maximum value in trades and find exact fits, even if it means involving additional teams.
In theory, the matchmaker GM brokering a three-team trade could try to play both sides and obfuscate whos getting what in the trade.
Neander lays all the cards on the table.
Advertisement The Rays are not only going to be creative and open-minded, Pittsburgh Pirates GM Ben Cherington said, but theyre going to be pretty honest about how theyre valuing players and honest about the different components of the deal.
That leads to trust.
In December, Cherington, pursuing lineup upgrades, was working with the Rays on a deal centered on second baseman Brandon Lowe.
Cherington was also talking to the Houston Astros, who wanted controllable starting pitching but werent inclined to trade big-league hitters.
Neander realized their trade talks already formed a triangle.
It pretty quickly turned into, maybe this is easier if we involve all three, Cherington recalled.
A couple calls later, a three-way text thread was established.
The resulting six-player trade ticked boxes on each teams offseason checklist.
Theres a reason the same clubs regularly appear in three-team trades.
Many of the GMs involved worked together in the past, and they know each other to be open to considering complicated solutions in order to piece the puzzle together.
Some front offices arent interested in such creativity.
The spiderweb sprawl of a three-team trade often starts from a kernel of interest, like the Athletics kicking the tires on Ruiz.
Initial trade talks rarely involve more than two teams.
The three-team concepts you dream up in your office and then pitch cold to the other two teams tend to not go very far, Cherington said with a laugh.
The necessary conditions for a three-team trade generally arise when theres smoke between two teams but no perfect match.
Team A has a surplus of pitching, but Team B needs a big bat.
Rather than throw up their hands, they might ask Team C about parting with a slugger for some pitching.
In other cases, the third team might elbow its way into a deal to access a player it couldnt otherwise.
The executives surveyed for this story explained the key to tri-team harmony is to clearly communicate what youre attempting to accomplish which can mean showing your cards and hoping it wont come back to haunt you and to understand other teams surpluses and needs.
At the 2012 Winter Meetings in Nashville, Cleveland GM Chris Antonetti was desperate for starting pitching, so he pursued Trevor Bauer, a top pitching prospect who had worn out his welcome with the Arizona Diamondbacks.
Antonetti was trying to move right fielder Shin-Soo Choo, who was entering a contract year, but the Diamondbacks wanted a shortstop.
They were after well-regarded Cincinnati Reds prospect Didi Gregorius.
Cincinnati wanted Choo.
Knowing all of this, Antonetti suggested a three-team arrangement and coordinated with Diamondbacks GM Kevin Towers and Reds GM Walt Jocketty until everyone was on board.
The trade ultimately involved nine players.
Advertisement Nine years later, Cleveland and Cincinnati reunited for another three-teamer involving Bauer.
This time, though, as Antonetti and Reds president Dick Williams wrapped up negotiations and awaited a postgame sign-off of medicals, they watched in horror as outfielder Yasiel Puig, a part of the trade, was in the center of a benches-clearing brawl at Great American Ball Park.
That one was a mess, Antonetti said.
They often are.
Seattle Mariners president of baseball operations Jerry Dipoto, a high-volume trader in sickness and in health, finalized a three-team deal in December 2018 from a Las Vegas hospital bed, where the gunslinger was being treated for blood clots in his lungs.
Another exec insisted he was once on the cusp of a significant trade, then invited a third team into the mix and watched the other two cut a deal without him.
One night when Perry Minasian, the now-former Los Angeles Angels GM, was a young staffer witnessing the whir of the Winter Meetings for the first time, he saw three executives huddled at a smoky hotel bar.
One would jot down a trade concept on a napkin and slide it to the next.
Technology has all but retired that sort of scene.
GMs now communicate via texts and calls, even when theyre under the same roof.
Only occasionally do the parties in a three-way trade jump on a call or initiate a group text thread.
Typically, one GM runs point.
In January, Reds president of baseball operations Nick Krall anchored talks on a three-team deal that started with a call to Minasian.
The Reds were interested in lefty reliever Brock Burke.
They dangled infielder Gavin Lux, but the Angels were looking for a lefty-hitting outfielder.
When Neander asked about Lux, Krall helped orchestrate a trade that sent Lux and an Angels pitching prospect to Tampa, Burke to Cincinnati and outfielder Josh Lowe to Anaheim.
Krall said the deal was pretty easy to complete.
That, for a three-team trade, Minasian echoed, (was) one of the easier ones Ive been a part of.
Advertisement But few trades, especially three-teamers, wind up closely resembling the initial concept that was proposed, one exec said.
If there were such a thing as a prevailing rule of three-team trades, its this: Be transparent.
If youre talking to a third team, keep the original partner in the loop.
Kansas City Royals president of baseball operations J.J.
Picollo fielded a call last winter from an exec with whom he had discussed a trade.
This time, the exec surprised Picollo by saying the GM from a third team was on the other line.
You get caught off guard, like, Wheres this going? Picollo said.
If youre acquiring a player intending to flip him to another team, say so.
There is some sportsmanship of, Hey, were gonna take your player and send him here, Preller said.
Some GMs wont care.
Others will ask that the player not be traded to a division rival or a team fighting them for a playoff spot.
When the Guardians traded infielder Andres Gimenez to the Toronto Blue Jays for first baseman Spencer Horwitz and a prospect in December 2024, Antonetti was direct with Torontos braintrust that he planned to flip Horwitz to the Pirates.
But there was a hurdle to clear: Horwitz had a wrist injury, and the Guardians couldnt trade him until the Pirates signed off on his medicals.
Had Pittsburgh not approved, Cleveland would have kept Horwitz.
So, what looks like a three-team trade on the surface was actually separate deals completed hours apart.
Ive learned its better to be upfront about what that whole picture is going to look like, said Guardians GM Mike Chernoff.
Youre not going to pull a fast one on someone.
In the end, Arnolds 2022 hairball included three teams and nine players.
The Braves wound up with Murphy; the As got four prospects and a backup catcher; the Brewers landed Contreras and two relievers.
Arnolds give-get calculation one prospect for two big leaguers and a Double-A arm checked out at the time.
It looks even better now.
Ruiz has bounced around the league, and Contreras is a three-time All-Star batting cleanup for the Brewers.
Advertisement All six of MLBs three-team trades since then have included Arnolds former Tampa colleagues.
The only non-Rays three-team trade of the past three years involved Freidman, the ex-Rays exec whose Dodgers are currently jockeying with Milwaukee for the best record in baseball.
In February, after finalizing his third three-team exchange of the offseason, Neander joked to MLB.com that the Rays only get attention for all their three-way trades because they havent executed a four-teamer.
It was said in jest, yet the sports most audacious instigators might take him up on it.
Oh yeah, I noodle on all that stuff, Arnold said.
If a two-team trade is like 1 in 100 and a three-team trade is, I dont know, 1 in 500, an AL executive said, a four-team trade is 1 in 5,000.
At the 1977 Winter Meetings, on the shores of Waikiki Beach in Honolulu, the New York Mets, Texas Rangers, Braves and Pirates consummated an 11-player blockbuster that stunned the baseball contingent gathered at the Sheraton-Waikiki Hotel.
As the elaborate arrangement was announced, Dodgers manager Tommy Lasorda looked on and quipped: This thing must have been put together by the teamsters.
That degree of complexity is no easier to hammer out a half-century later.
Today, four-team trades are little more than whiteboard fodder.
God, I can only imagine, Anthopoulos said.
Youd have to be really motivated.
Chernoff said the mere suggestion of a fourth team a Hail Mary when the optimism of a three-team setup is fading can torpedo a conversation.
Thats when were like, Theres no chance, he said.
Lets be realistic here.
Krall was an Athletics intern in 2002, when they were discussing a deal that eventually expanded to include the Reds, Diamondbacks and Toronto Blue Jays.
Krall just so happened to be interviewing for a full-time gig with the Reds as the trade was materializing at the Winter Meetings in Nashville.
He bounced between the teams hotel suites as they reached the finish line on a four-player reassignment: Erubiel Durazo to the Athletics, Elmer Dessens to the Diamondbacks, Felipe Lopez to the Reds and prospect Jason Arnold to the Blue Jays.
It was crazy, Krall said.
Advertisement Ten years later, at another Winter Meetings, Arnold was working the whiteboard as the Rays shopped pitchers James Shields and Wade Davis.
Before settling on a seven-player swap with the Royals, they pondered permutations of a four-team trade that also included the Diamondbacks and Rangers.
The simpler structure proved to be the winner.
But the head-spinning four-team concept was undeniably more fun.
To some maestros of the whiteboard, the wackier, the more parties involved, the better.
Id say 99.7 percent of the things we work on never happen, Arnold said, but theyre fun to dream on.