The trade winds around Orioles shortstop Manny Machado are finally swirling in earnest, but it’s a couple of years too late for Baltimore to truly cash in on a player who just turned 26 and is a middle-of-the-order hitter who can play either a passable shortstop or a generationally great third base.

See, Machado is what’s known in baseball parlance as “a rental,” since he’s a free agent at the end of the season, and that impacts his trade value—two months, plus playoffs, of Machado are worth a lot less than several seasons’ worth of Machado. But that doesn’t mean that two or three months’ worth of Machado can’t be valuable. Calling Machado “a rental” makes him sound like a temp. Well, he isn’t a stopgap; he’s Superman.

Baseball Prospectus’s WARP has Machado as the 13th-most valuable position player in baseball this year. Pretty much every contender except the Astros, who already have more shortstops than they can use, has been linked to Machado in the past week. Cleveland is the only one of those teams for which Machado wouldn’t represent a substantial immediate upgrade at either shortstop or third base. But even then, Cleveland’s third baseman, José Ramirez, could move to plug a hole almost anywhere else on the diamond.

And yet, to my immense puzzlement and the Orioles’ peril, the trade market for Machado seems a little tepid. No top prospects—Milwaukee’s Keston Hiura, Philadelphia’s Sixto Sanchez, Los Angeles’s Yadier Alvarez—seem to be shaking loose, and even lesser youngsters, like Yankees pitching prospect Justus Sheffield and Phillies right-hander Zach Eflin, look likely to stay put as these clubs appear content to pass on a superstar upgrade for the time being and maybe take a run at Machado in the offseason.

That caution works as a bargaining position, but is it a sound team-building strategy? The fear when moving a big-name prospect for a so-called rental is that the club will bounce out in the first round of the playoffs while the prospect it gave up will go on to become, well, the next Manny Machado. Last week, Jeff Sullivan of FanGraphs looked at deadline rental trades for five-win players over the past four years in an attempt to pin down what the market ought to look like, but I want to go back a little further in time to see how rental trades shake out: How many times do buyers actually regret them?

Notable Rental Trades

2017: Dodgers trade minor league pitcher A.J. Alexy, 2B/OF Willie Calhoun, and INF Brendon Davis to Texas for RHP Yu Darvish

Did it work? No. Darvish was great (121 ERA+, 11.1 K/9) in nine regular-season starts, but the Dodgers had already locked up the division, and after two strong starts in the NL playoffs, Darvish got annihilated in two World Series starts. He allowed nine runs in just 3 1/3 innings and took the loss in Game 7.

Has it come back to bite them? Not so far. Calhoun can really hit, but he’s yet to establish himself with the Rangers and will probably be a left fielder when he does.

Should they regret it? Jury’s still out, but Darvish was the best pitcher on the market at the time, and it was worth a shot. The process was sound, even if the result didn’t pan out.

2016: Dodgers trade pitching prospects Frankie Montas, Grant Holmes, and Jharel Cotton to Oakland for LHP Rich Hill and OF Josh Reddick

Did it work? Sort of. Hill, like Darvish, was great down the stretch and inconsistent in the playoffs: one loss in a bad start, one win in a great start, and one 2 2/3–inning, 55-pitch start on three days’ rest in Game 5 of the NLDS against the Nationals. This was the game where Kenley Jansen threw 51 pitches and Clayton Kershaw had to come in out of the bullpen to get the save. Hill re-signed after the season. Reddick, who was terrible in L.A., didn’t.

Has it come back to bite them? Not really. Holmes is still in the minors, and neither Cotton nor Montas has been so good the Dodgers would miss him, though Montas has a 3.35 ERA in eight starts with Oakland this year, so this could change.

Should they regret it? Not at all.

2016: Nationals trade LHPs Felipe Vázquez and Taylor Hearn to Pittsburgh for RHP Mark Melancon

Did it work? Hell yes! Melancon posted a 1.82 ERA and 17 saves in 29 2/3 post-trade innings, then made four more scoreless appearances in the NLDS.

Has it come back to bite them? Hell yes! Vázquez, who’d already debuted at the time of the trade, became Pittsburgh’s closer the next year. Since then he’s saved 42 games, posted a 2.18 ERA and 11.2 K/9 ratio, and made the 2018 All-Star team. Melancon walked after the season.

Should they regret it? Hell yes! This is why you don’t fill a role with veterans by trading away young players who could fill the role themselves—specifically why Miguel Andújar and Gleyber Torres won’t go back to Baltimore if Machado gets traded to the Yankees. (Washington sort of made the same mistake last year by shipping off Blake Treinen to Oakland in the Ryan Madson–Sean Doolittle trade, though while Treinen’s been exceptional in 2018, he was lost in the woods last year and wouldn’t have helped down the stretch in 2017.)

2016: Cubs trade minor league shortstop Gleyber Torres, minor league outfielders Billy McKinney and Rashad Crawford, and RHP Adam Warren to the Yankees for LHP Aroldis Chapman

Did it work? Yes. Chapman allowed just three earned runs in 28 appearances down the stretch for the Cubs, then appeared in 13 of Chicago’s 17 postseason games, winning two games and saving four more en route to the team’s first World Series victory in 108 years.

Has it come back to bite them? Absolutely. Torres, who was a top-50-level prospect two years ago, blossomed into a 21-year-old All-Star as a rookie this year.

Should they regret it? This was a huge price to pay, both in terms of prospects and in terms of moral compromise, and I said so at the time.

On one hand, while the Cubs got three great months (and a title) out of Chapman, Torres might be a 20-win player or more by the time he hits free agency in 2025. And besides, when the Cubs handed Chapman a lead in Game 7 of the World Series, he coughed it up—maybe they could’ve won the World Series without him.

On the other hand, Torres has turned into the best-case-scenario version of himself—there’s no guarantee the Cubs could have turned him into the player he is now with the Yankees, who might be the best in the business at player development. The Cubs have done a good job with their middle infield prospects, but Addison Russell, Javy Báez, and to a lesser extent Ian Happ are very different players than what they were expected to become as teenagers. Still, those three and Kris Bryant are all very good players—it’s not like Chicago has a Torres-shaped hole in its lineup.

But worrying about Torres being too high a price to pay for Chapman is frankly kind of a soulless way to look at baseball. The Cubs won the World Series—their first in 108 years, it bears repeating—by one run in extra innings of Game 7. Championship margins don’t get thinner than that, and Chapman was a huge part of making that happen. Ask Cubs fans if they’d give up that title, or even risk giving it up, in order to have Torres back. And if they say yes, kick them in the shins and tell them to stop being such grumps.

Personally, I think there’s only one good reason to regret this trade, and it has to do with Chapman, not Torres. One of the arguments against trading for Chapman was that the Yankees had traded for him after he’d been suspended following his girlfriend’s account that he choked her, then flipped him for a huge profit after the rancor had died down a little. It has to sully even memories of a championship if a guy like that’s on the cover of the commemorative DVD, though last year’s allegations of domestic abuse against Russell are, if nothing else, a reminder that men like Chapman are all too common in the baseball world.

2015: Blue Jays trade pitchers Daniel Norris, Matthew Boyd, and Jairo Labourt to Detroit for LHP David Price

Did it work? Pretty much. Price posted a 2.30 ERA in 11 starts after the trade, and the Blue Jays not only made the playoffs for the first time since 1993 but advanced to the ALCS. In the playoffs, Price posted a 6.17 ERA, but that Toronto playoff run was one of the most exciting in recent MLB history.

Has it come back to bite them? No. Boyd and Norris have pitched extensively in Detroit, neither all that well. Boyd’s a decent innings eater, but a replaceable one. He’s not the difference between Toronto contending and not in 2018.

Should they regret it? Just as the Cubs might have won it all without Chapman, the Blue Jays could’ve had this moment without Price.

But if I were a Jays fan, I wouldn’t want to risk screwing with the timeline by going back to undo this trade.

2015: Royals trade pitchers Brandon Finnegan, Cody Reed, and John Lamb to Cincinnati for RHP Johnny Cueto

Did it work? Yes. Cueto posted a 4.76 ERA down the stretch, and was inconsistent in four playoff starts. But he threw eight innings of two-run ball in the ALDS clincher against Houston, then pitched a complete game against the Mets in Game 2 of the World Series.

Has it come back to bite them? In 24 starts with the Reds, Lamb was 2-12 with a 6.17 ERA. Finnegan’s career highlight remains pitching in the College World Series and MLB World Series in the same year, which he did before the Royals traded him.

Should they regret it? No. Flags fly forever.

2015: Mets trade minor league pitchers Luis Cessa and Michael Fulmer to Detroit for OF Yoenis Céspedes

Did it work? I trashed this trade when it happened. The Mets, as you might remember, almost traded a package involving Wilmer Flores to Milwaukee for Carlos Gómez, who was a better defender than Céspedes and signed for an extra year. The deal was close enough to being completed that Flores thought it was done when he took the field against San Diego, as the lifelong Met famously wept on the field.

I thought the Mets made a mistake by moving on from Gómez, and I’ve seldom been more wrong. Céspedes hit 17 home runs in 57 games with the Mets and became an instant cult hero, and the Mets made the World Series. Meanwhile, Gómez spent 12 months in Houston, in which he hit .221/.277/.342 in 486 plate appearances and became an instant pariah.

Has it come back to bite them? A little. Céspedes, who re-signed in New York that offseason, is getting old and slowing down, while Fulmer was the AL Rookie of the Year in 2016. And while the Mets aren’t in last place for lack of starting pitching, they could probably use a guy like Fulmer, as could 27 or 28 other teams.

Should they regret it? Absolutely not. Céspedes, like Price, solidified the team and galvanized the city. Much as I hated the deal at the time, I’d do it 100 times out of 100.

2014: Orioles trade minor league pitcher Eduardo Rodríguez to Boston for LHP Andrew Miller

Did it work? Miller allowed three earned runs and struck out 34 against four walks in 20 regular-season innings, then allowed no runs and only three base runners in 7 1/3 playoff innings. The Orioles made the ALCS but got swept by Kansas City.

Has it come back to bite them? Rodríguez has been frustrating in parts of four seasons in Boston, but on the aggregate he’s been a perfectly fine midrotation starter. Which is to say that if he’d developed the same way in Baltimore, he’d be the best homegrown Orioles starter since Mike Mussina.

Should they regret it? Probably, though everything about the Buck Showalter Orioles has been weird, particularly the bullpen, so it’s hard to say.

2011: Giants trade minor league pitcher Zack Wheeler to the Mets for OF Carlos Beltrán

Did it work? This is what you’re afraid of when you’re looking at a rental. Wheeler was the no. 38 prospect on the BP midseason top 50 that year, and eventually the first of what became an endless supply of power righties to come up with the Mets in the 2010s. Beltrán, at age 34, was awesome that year: He hit .323/.369/.551 in 44 games with the Giants, but San Francisco went 25-32 after the trade and finished out of the playoffs.

Has it come back to bite them? Not as badly as it could have, considering how Wheeler’s struggled to stay healthy, but this is not a great moment for the Giants.

Should they regret it? Sometimes the move that’s supposed to put you over the top doesn’t put you over the top, which is why it’s often safer for teams that already have a playoff spot to consolidate their position through trades, rather than teams on the wrong side of the bubble trying to squeeze into the party.

2009: Cardinals trade pitcher Clayton Mortensen, outfielder Shane Peterson, and infielder Brett Wallace to Oakland for outfielder Matt Holliday

Did it work? More or less. Holliday hit .353/.419/.604 in 63 games after the trade, and St. Louis had the second-best record in the National League. But the Cardinals got swept in the NLDS, scoring just six runs in three games against the Dodgers.

Has it come back to bite them? No. Almost nine months earlier, the A’s had given Colorado a three-player package for Holliday that included Carlos González and Huston Street. By contrast, none of the three players St. Louis gave up ever amounted to anything. Wallace is the most famous of the bunch, and only because he got traded almost every year.

Should they regret it? No way. Holliday clearly liked it in St. Louis, enough that he signed a seven-year deal to stay there. Over those seven seasons, Holliday produced 20.9 bWAR and made four All-Star teams, while the Cardinals went to the playoffs five times, winning two pennants and a World Series.

2008: Brewers trade minor league pitchers Rob Bryson and Zach Jackson, 1B Matt LaPorta, and OF Michael Brantley to Cleveland for CC Sabathia

Did it work? Hell yes. Everyone knew Sabathia was never going to re-sign in Milwaukee, so the Brewers traded for him early and rode him like an old Toyota. Sabathia made 17 regular-season starts, his last three on three days’ rest, and from his debut on July 8 through the end of the regular season, Milwaukee went 14-3 when he pitched and 27-29 when he didn’t. Sabathia threw seven complete games—three of them were shutouts and in a fourth he allowed only a single unearned run—and allowed a 1.65 ERA in 130 2/3 innings, and the Brewers needed every strikeout. Co-ace and fellow free-agent-to-be Ben Sheets suffered a torn UCL on the eve of the playoffs, and Milwaukee won the wild card by a single game over the Mets. Sabathia finished fifth in NL Cy Young voting and sixth in NL MVP voting despite playing half the season in the American League.

Has it come back to bite them? Milwaukee was so close to getting away with a heist as LaPorta, the tentpole of this trade, busted. But Brantley, a player to be named later in the deal, just made his third All-Star team for the Indians.

Should they regret it? Milwaukee lost the NLDS in four games to the Phillies, and Sabathia’s most memorable playoff contributions were walking opposing pitcher Brett Myers and allowing a grand slam to Shane Victorino that broke the series open. So it could’ve gone better, and it would have been a different series if Sheets hadn’t gotten hurt. But let me put it this way: From then until now, with the Brewers back in the NL Central race, what Milwaukee baseball event has been more fun than Sabathia’s 2008 stretch run? When have the Brewers been more nationally relevant? I don’t think they’ve topped Sabathia’s contributions in the decade since.

2004: As part of a three-team deal, the Astros trade away pitcher Octavio Dotel and catcher John Buck and receive OF Carlos Beltrán

Did it work? Beltrán was pretty good in 90 games in Houston (.258/.368/.559 with a perfect 28-for-28 in stolen base attempts), but not nearly as good as he was in the playoffs. In 12 playoff games, Beltrán hit .435/.536/1.022 with eight home runs and six steals in six attempts, which is one of the best playoff performances by a position player in MLB history.

Has it come back to bite them? No.

Should they regret it? No. This is the best-case scenario for a rental, and even if they missed Dotel and Buck, those losses didn’t prevent the Astros from making the World Series in 2005.

1998: Astros trade pitchers Freddy García and John Halama and shortstop Carlos Guillén to the Seattle Mariners for LHP Randy Johnson

Did it work? The Big Unit won 10 of his 11 starts and posted a 1.28 ERA with Houston, as the Astros won 102 games. In those 11 starts Johnson was worth 4.3 bWAR and 3.7 wins above average.

Has it come back to bite them? Yeah. Because while Johnson managed to go 0-2 with a 1.93 ERA in two NLDS starts, García, Halama, and Guillén were instrumental in building the post-Griffey and later post-A-Rod Mariners, including the team that won 116 games in 2001.

Should they regret it? It’s not Johnson’s fault the Astros didn’t win it all in 1998, but it shows that there’s a danger to trading for a future free agent even if he delivers on the hype.

This list of trades should serve to underscore how great an impact one player can make in the highest-leverage part of the year, even if he does leave via free agency at season’s end. It also shows, as in the cases of Chapman for Torres, Céspedes for Fulmer, or Sabathia for Brantley, how a short-term impact can be worth it even if the team gives up a player who goes on to stardom elsewhere. In other words, you can achieve the goal of a trade without necessarily winning out in terms of value—indeed, that’s the scenario in which the most people walk away happy.

And even if the club doesn’t achieve its goals and the players it gives up go on to prosper, that doesn’t necessarily hamstring the future. Sure, the 1998 Astros traded away three very good players for Johnson, but they still managed to develop Lance Berkman, Roy Oswalt, Brad Lidge, Morgan Ensberg, and the rest of a core that was in their farm system at the time of the Johnson trade and became the backbone of the team that contended for titles in 2004 and 2005.

Finally, because these free agents aren’t under team control, all trade partners go into the negotiation under the tacit acknowledgement that the target—Machado in this case—isn’t worth a potentially franchise-ruining prospect return. Giving up a huge prospect haul for a cost-controlled superstar (Boston trading no. 1 overall prospect Yoán Moncada, plus three other prospects, for Chris Sale is the most extreme recent example) can pay off huge, but it can also backfire.

The trades we look back on years later, the real laughers, tend to be for players with at least a full year’s worth of team control for free agency. Remember the deadline deal in which the Expos GM sent Lee Stevens plus three future All-Stars (Cliff Lee, Grady Sizemore, and Brandon Phillips) to Cleveland at the 2002 trade deadline for Bartolo Colón? Colón had another year’s worth of team control but lasted only half a season in Montreal before the franchise flipped him to the White Sox before the 2003 season.

The same thing happened to Jeff Samardzija in 2014—the A’s traded a package that included Addison Russell and Billy McKinney to get the Cubs right-hander, who had a year and a half left on his deal, but after one failed stretch run they, too, shipped him off to the White Sox in December of that year.

Or how about the February 2008 laugher in which Seattle sent five players to Baltimore for lefty Erik Bedard, only to see Bedard’s career crater and three of those five youngsters (Adam Jones, Chris Tillman, and George Sherrill) turn into All-Stars themselves? Bedard had two years of team control left before he hit free agency.

My favorite example, though, came in 2007, when Atlanta traded rookie catcher Jarrod Saltalamacchia and four prospects (including Matt Harrison, Elvis Andrus, and Neftalí Feliz) to Texas for a year and a half of first baseman Mark Teixeira. After 12 months, Atlanta flipped Teixeira to Anaheim for Casey Kotchman. Teixeira hit .358/.449/.632 in 54 games, went 7-for-15 with four walks in the ALDS, and signed with the Yankees as a free agent, leaving the Angels with two compensation picks, which they used to select Mike Trout and Tyler Skaggs.

Besides, assuming that you can just sign Machado this offseason is a dangerous game, because he can sign in only one place. And while Machado is unlikely to sign an extension before free agency, giving him a couple of months to settle in can make for a powerful sales pitch. For example: Céspedes re-signed with the Mets in 2015 and Matt Holliday re-signed with the Cardinals after landing there at the 2009 deadline. If nothing else, the team that trades for Machado will have an extra three months to negotiate with him before other teams can make formal offers.

Most of the time, the biggest risk to trading for a player like Machado is that he’ll give you what you want, but it’ll end up costing more in the long run. True rental trade disasters happen only once or twice a decade—if anything, the peril is in overvaluing team control compared to the talent of the player you’re acquiring. The object, after all, isn’t to win the trade; it’s to win the World Series.