What’s the precedent for a Machado deal? Looking at MLB trades in the past decade that involved a young superstar before his walk year

As trade rumors swirl around Manny Machado, fans and media have speculated on what kind of return package the Orioles might get if they trade their star third baseman.

Can the Orioles land a bounty of top-100 prospects? Can they get a major league ready starting pitcher? Some combination of both? Neither?

To offer an idea of what to expect, I pored through the last 10 years of MLB trades looking for similar deals involving star players. To narrow my search, I looked for trades of players who — like Machado — fit the following criteria:

• The player was younger than 30 at the time of the trade.

Players who are in their prime or approaching their prime tend to fetch a better return than over-30 players whose best years are likely behind them. Machado is 25, so that should affect the quality of prospects the Orioles would get in a trade.

• The player had at least a 15 career WAR and multiple MLB honors.

I’m looking for star players who provided a lot of value to their teams. I set 15 WAR (using Baseball Reference) as a minimum; anyone below that mark probably hadn’t yet established themselves as a star. I’m also looking for players who received plenty of recognition around MLB for their achievements, such as All-Star selections, Gold Gloves and/or Top 10 voting in year-end awards (MVP, Cy Young, Rookie of the Year). Machado, for instance, has a 27.9 career WAR, three All-Star selections, two Gold Gloves and three Top 10 MVP finishes.

• The player had one season remaining until free agency.

This is an important caveat. Generally, a player who has only one season left on his contract isn’t going to command as much of a return as someone with multiple years of team control. I’m also not including pending free agents who were traded during the season, since their new teams didn’t get a full year out of them. I’m looking for players with exactly one year remaining on their contracts at the time of the trade — no more, no less.

I found five trades in the last decade that fit the criteria. Here’s a look at how those deals panned out.

The Johan Santana trade (Feb. 2, 2008)

The trade: The Minnesota Twins dealt Santana to the New York Mets for OF Carlos Gomez, RHP Deolis Guerra, RHP Philip Humber and RHP Kevin Mulvey.

How it happened: Santana was arguably the best pitcher in baseball at the time, a 28-year-old power lefty who’d won two Cy Young awards and finished in the Top Five of the voting two other times. During his four full seasons in the Twins’ rotation, he led the AL in ERA twice and led in strikeouts and WHIP three times each. But the small-market Twins knew they wouldn’t be able to re-sign Santana when he was eligible for free agency after 2008, so they traded him away before the season began.

After a bidding war that involved the Red Sox and both New York teams, among others, the Twins found a match with the Mets. In exchange for Santana, they received four prospects, all of whom were 25 or younger. Gomez and Guerra were both ranked among the top 100 prospects in baseball by both Baseball America and Baseball Prospectus, and Humber and Mulvey were close to big league-ready arms.

The results: The return package could hardly have turned out worse for the Twins. All four prospects turned into duds, at least while they were in a Minnesota uniform. The three pitchers combined for only 15 appearances with the club, posting a 7.36 ERA. Humber had one moment of glory in the majors when he pitched a perfect game in 2012 — but he did so as a member of the Chicago White Sox, three years after the Twins jettisoned him.

The only prospect in the trade who saw major time with the Twins was Gomez, who became their starting center fielder at age 22 in 2008. But the free-swinging Gomez struggled in his two seasons in Minnesota, and the Twins dealt him to Milwaukee for a name that’s familiar to Orioles’ fans: shortstop J.J. Hardy. (Compounding the Twins’ problems, they then traded Hardy after one season to the Orioles for forgettable relievers Jim Hoey and Brett Jacobson, while Gomez emerged as an All-Star for the Brewers and Hardy an All-Star for the Orioles.)

Meanwhile, the Mets signed Santana to a six-year, $137.5 million extension during a negotiating window that completed the trade. They got their money’s worth in the first year of the deal when Santana went 16-7 with a league-leading 2.53 ERA, finishing third in the NL Cy Young vote. But Santana’s body broke down and he missed time with injuries every season after 2008. He pitched four seasons with the Mets, finishing with a 46-34 record and 3.18 ERA in 109 starts. In 2012, his final year, he threw the franchise’s first no-hitter.

As a postscript to the Santana tale, he joined the Orioles on a minor league deal in 2014 and was primed to return to the majors until he tore his Achilles tendon at extended spring training in June, ending his season — and, effectively, his career.

The Matt Holliday trade (Nov. 10, 2008)

The trade: The Colorado Rockies traded Holliday to the Oakland Athletics for OF Carlos Gonzalez, LHP Greg Smith and RHP Huston Street.

How it happened: Holliday wasn’t quite the all-around player that Machado is; he never had much of a glove, playing a passable (at best) left field. But, boy, the guy could hit, even accounting for the Coors Field bump that inflated his home stats. Holliday was a three-time All-Star and was the NL MVP runner-up in 2007, when he hit .340 with a 1.012 OPS, 36 homers and 137 RBIs. Holliday, a Scott Boras client, was unlikely to re-sign in Colorado when he reached free agency after the 2009 season.

The low-spending Athletics were a surprising trade match for Holliday, as they didn’t stand a chance of signing him, either. But they hoped he would jolt an Oakland offense that scored the fewest runs in the majors the previous season. They paid a hefty price to find out, giving up five-tool rookie outfielder Gonzalez as well as their closer, Street, and their team leader in starts in 2008, Smith.

The results: The trade will go down as one of the worst in Billy Beane’s history as Oakland’s general manager. While Smith was no loss — he made only eight starts for Colorado — Street served as the Rockies’ closer for three years.

Even if those two players hadn’t been involved, though, giving up Gonzalez alone for Holliday was a giant mistake. Gonzalez spent the next nine seasons as a mainstay in the Rockies’ lineup, amassing a 22.9 WAR over that span and finishing third in NL MVP voting in 2010.

Holliday, meanwhile, never seemed to fit in with the Athletics. Moving from hitter-heaven Coors to spacious Oakland Coliseum dampened his offensive numbers, and with the A’s languishing in last place in late July, they flipped Holliday to the St. Louis Cardinals. He spent the next eight years in St. Louis, making four All-Star teams. The prospects the Athletics received in the second Holliday trade weren’t anywhere near as productive as the players they gave up to acquire him. Beane came out on the losing end of the Holliday experiment.

The Adrian Gonzalez trade (Dec. 6, 2010)

The trade: The San Diego Padres traded Gonzalez to the Boston Red Sox for OF Rey Fuentes, RHP Casey Kelly, 1B Anthony Rizzo and IF Eric Patterson.

How it happened: Being traded is nothing new for Gonzalez, who has been dealt five times in his career — spanning from 2003 (when he was a minor leaguer) to this past Saturday, when the Los Angeles Dodgers foisted him on the Atlanta Braves to clear his salary. This particular trade, between the Padres and Red Sox, was the third involving Gonzalez and came in the prime of his career.

Gonzalez was 28 and was coming off three consecutive All-Star seasons for the Padres. He was a two-time Gold Glove first baseman who’d had four straight years of 30 or more homers and 99 or more RBIs, no easy feats to accomplish at San Diego’s cavernous Petco Park. The Padres saw no chance to re-sign him once his contract was up, so they sent him to the big-budget Red Sox, who agreed to parameters of an extension with Gonzalez during a negotiating window. Ultimately, they inked him to a seven-year, $154 million extension.

The Padres received a slew of young players, headlined by Kelly and Rizzo, both among Baseball America’s top 100 prospects.

The results: Neither team, as it turned out, really got what they wanted out of the trade. None of the Padres’ prospects flourished in San Diego. Fuentes and Patterson (the brother of former Oriole, Corey) combined for 70 games and went 21-for-122 (.172) between them. Kelly pitched just nine games, posting a 6.69 ERA. As for Rizzo, the Padres gave up on him way too soon, trading him to the Chicago Cubs for righty Andrew Cashner after one disappointing season. Rizzo has since become an All-Star first baseman and won a World Series with the Cubs.

Gonzalez’s Red Sox career was unexpectedly short; he lasted less than two seasons into his seven-year deal. After an All-Star campaign in 2011, Gonzalez was dealt to the Dodgers in 2012 in a shocking salary-dump trade that also sent Josh Beckett and Carl Crawford to Los Angeles. For Orioles fans, the most lasting image of Gonzalez in a Red Sox uniform may be when emergency pitcher Chris Davis struck him out swinging in a classic 17-inning marathon at Fenway Park in 2012. Gonzalez is now a free agent after being released by the Braves on Monday.

The Jason Heyward trade (Nov. 17, 2014)

The trade: The Braves traded Heyward and RHP Jordan Walden to the Cardinals for RHP Shelby Miller and RHP Tyrell Jenkins.

How it happened: If there’s one player on this list who most closely matched Machado when he was traded, it’s Heyward. He was 25 years old when he was dealt, the same age Machado is now. Heyward had a career 24.6 WAR; Machado’s is 27.9. And while Heyward didn’t have Machado’s power, he was better at getting on base and a much better runner. Both Heyward and Machado are elite defenders, having won two Gold Gloves apiece by age 25.
The Braves were in full rebuilding mode when they sent Heyward to St. Louis. The key return piece was Miller, a pre-arbitration righty who’d spent two full years in the Cardinals’ rotation and had a career 26-18 record and 3.33 ERA. The Braves also threw in veteran reliever Walden and received Jenkins, a lower-level prospect.

The results: The Cardinals got exactly what they hoped for out of Heyward, who batted .293 with a .797 OPS and collected his third Gold Glove, helping St. Louis win 100 games and the NL Central in 2015. The Cardinals, though, lost the Division Series to the Cubs, who then signed Heyward as a free agent that winter. The Cardinals received a compensatory draft pick for losing Heyward, which they used on righty Dakota Hudson, currently ranked their No. 9 prospect by Baseball America.

Meanwhile, the Heyward trade is the gift that keeps on giving for the Braves. Miller spent one year with Atlanta and pitched quite well, registering a 3.02 ERA in 32 starts — although he led the majors with 17 losses because the team around him was terrible.
The Braves were able to parlay that into a mega-deal with the Arizona Diamondbacks after the 2015 season, acquiring former No. 1 overall draft pick Dansby Swanson and outfielder Ender Inciarte for Miller. Swanson struggled in 2017, but is just 23 and could be Atlanta’s shortstop for years to come, while Inciarte has already racked up two Gold Gloves and an All-Star appearance in two years with the Braves. Miller, meanwhile, collapsed to a 6.15 ERA for Arizona in 2016 and underwent Tommy John surgery in 2017.

The Justin Upton trade (Dec. 9, 2014)

The trade: The Braves traded Upton and RHP Aaron Northcraft to the Padres for LHP Max Fried, OF Dustin Peterson, IF Jace Peterson and OF Mallex Smith.

How it happened: In his first offseason as San Diego’s general manager, A.J. Preller went all-in on transforming the perpetually also-ran Padres into contenders. He reshaped his roster with trades for outfielders Matt Kemp and Wil Myers, closer Craig Kimbrel, starter James Shields and others. His biggest move was acquiring Upton, a two-time All-Star who’d compiled 20.4 career WAR by age 27, to complete his outfield. The rebuilding Braves received a pair of unrelated Petersons, the speedy Smith and the prized prospect of the haul, the 20-year-old lefty Fried.

The results: Preller’s go-for-broke strategy didn’t work. The Padres finished a disappointing 74-88 in 2015, although Upton contributed 28 homers and 81 RBIs. The Padres gave him a qualifying offer and received draft pick compensation when he signed with the Detroit Tigers as a free agent. They drafted Hudson Potts, an infielder ranked No. 23 in the system by MLB.com.

The outcome for the Braves’ half of the trade remains to be seen. Smith has since been traded twice more, to the Seattle Mariners and Tampa Bay Rays, while Jace Peterson is a free agent after three mediocre years for the Braves. Fried missed two seasons after Tommy John surgery but made his big league debut in 2017 and is the Braves’ No. 8 prospect, according to MLB.com, while Dustin Peterson reached Triple-A Gwinnett last season and is ranked No. 14.