How Every MLB Team Would Use a 21st-Century Do-Over
Let's for a minute imagine that a magical genie has decided to grant each MLB franchise one mulligan to use on any decision made during the past 20 years. How would they each proceed?
It's the ultimate hypothetical: one do-over to set right a grievous error that has haunted the front office and fanbase alike for years.
Fernando Tatis Jr. taking the league by storm in a Chicago White Sox uniform. Manny Ramirez playing his entire career with the Cleveland Indians. Chris Davis no longer cashing checks signed by the Baltimore Orioles.
Ahead, we've made that tough decision for all 30 MLB teams, combing through trades, free-agent signings, and various other decisions over the last 20 years.
More times than not, the bad trade got the nod over the bad free-agent signing. Someone was going to sign those players, and most teams wading in the deep end of the free-agent pool have a ton of money to spend anyway. Losing young, cost-controlled talent almost always hurts more than whiffing on a big signing.
The only thing off-limits was altering the MLB draft. Otherwise, the answer for 21 teams would have simply been "Draft Mike Trout" after they passed on him in 2009, and that would have made for a boring article.
Arizona Diamondbacks: Trading SP Max Scherzer
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Dec. 8, 2009:Â Arizona Diamondbacks traded SP Max Scherzer, RP Daniel Schlereth in a three-team trade with the Detroit Tigers and New York Yankees for SP Ian Kennedy, SP Edwin Jackson.
At the time, Max Scherzer was far from the headliner in this three-team, seven-player winter meetings deal that also included Curtis Granderson and a young Austin Jackson.
In fact, the decision paid immediate dividends for the D-backs in the form of Kennedy, who ascended to the role of staff ace. He went 21-4 with a 2.88 ERA to finish fourth in National League Cy Young voting and help lead the team to an NL West title in 2011, but he quickly faded in the years to come.
Scherzer flashed frontline potential but was inconsistent during his first three seasons in Detroit before everything fell into place in 2013.
He went 21-3 with a 2.90 ERA, 0.97 WHIP and 240 strikeouts in 214.1 innings that season to win American League Cy Young honors. That kicked off an incredible seven-year stretch that has seen him post 46.7 WAR while finishing in the top five of Cy Young voting every year and winning the award two more times.
Runner-Up: OF Yasmany Tomas signed to a six-year, $68.5 million deal (Dec. 9, 2014).
Atlanta Braves: Selling the Farm for 1B Mark Teixeira
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July 31, 2007: Atlanta Braves traded SS Elvis Andrus, RP Neftali Feliz, SP Matt Harrison, C Jarrod Saltalamacchia, RP Beau Jones to the Texas Rangers for 1B Mark Teixeira, RP Ron Mahay.
Here's a quick rundown of where the players included in this blockbuster trade package ranked in the Atlanta Braves farm system and leaguewide, according to Baseball America:
- C Jarrod Saltalamacchia:Â No. 1 ATL prospect, No. 36 MLB prospect
- SS Elvis Andrus: No. 2 ATL prospect, No. 65 MLB prospect
- SP Matt Harrison:Â No. 3 ATL prospect, No. 90 MLB prospect
- RP Beau Jones:Â No. 14 ATL prospect
- RP Neftali Feliz:Â No. 16 ATL prospect
Goodness.
Teixeira hit a gaudy .317/.404/.615 with 17 home runs and 56 RBI in 54 games following the trade, but the Braves went just 29-27 the rest of the way and missed the postseason.
When it became clear he was not going to sign a long-term deal in Atlanta, he was flipped again the following summer for the middling return of Casey Kotchman and Stephen Marek.
Legendary general manager John Schuerholz was chasing one last postseason trip in his final year on the job, and it wound up costing the Braves considerable young assets.
Runner-Up: SP Adam Wainwright, SP Jason Marquis, RP Ray King traded to the St. Louis Cardinals in exchange for OF J.D. Drew, C/OF Eli Marrero (Dec. 13, 2003).
Baltimore Orioles: Bidding Against Themselves to Re-Sign 1B Chris Davis
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Jan 21, 2016: 1B Chris Davis re-signed to a seven-year, $161 million deal.
Slugger Chris Davis was one of the premier bats on the 2015-16 free-agent market after posting a 147 OPS+ while leading the AL with 47 home runs during a 4.9-WAR season in 2015.
However, he also led the AL in strikeouts (208) and was just a year removed from hitting a brutal .196 with a 96 OPS+, so there were some red flags. That didn't stop the Orioles from making him a seven-year, $150 million offer, and when his free agency stretched into the new year, he eventually agreed to a $161 million pact.
The thing is, no one else seemed to be a serious contender for his services. Rather than using that as leverage, the O's seemingly bid against themselves and wound up giving him more money.
While he hit 38 home runs in the first year of the contract, his production has since bottomed out, and he's been worth an ugly minus-2.3 WAR over the first four seasons. Now in a full-scale rebuild, the Orioles are still on the hook for $69 million over the next three years.
Runner-Up: SP Jake Arrieta, RP Pedro Strop traded to the Chicago Cubs for SP Scott Feldman, C Steve Clevenger (July 2, 2013).
Boston Red Sox: Signing 3B Pablo Sandoval
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Nov. 25, 2014: Pablo Sandoval signed to a five-year, $95 million deal.
After hitting .366/.423/.465 in 17 postseason games to help the San Francisco Giants win their third World Series title in five years, Pablo Sandoval hit the open market.
With hyped prospect Will Middlebrooks failing to live up to expectations, the Boston Red Sox had a hole to fill at third base, and Sandoval became their No. 1 free-agent target. He was quickly inked to a massive five-year deal on the same day that Hanley Ramirez agreed to a four-year, $88 million pact of his own.
What followed was an unmitigated disaster.
Sandoval would play just 161 games in a Red Sox uniform over parts of three seasons, logging a 71 OPS+ and minus-1.6 WAR before he was given his outright release on July 19, 2017.
Aside from his own individual struggles, the Sandoval signing also likely played a part in the team's decision to trade Travis Shaw to the Milwaukee Brewers, where he went on to post back-to-back 30-homer seasons.
Runner-Up: SP Jon Lester low-balled with a four-year, $70 million extension offer (Early 2014).
Chicago Cubs: Trading OF Eloy Jimenez and SP Dylan Cease
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July 13, 2017:Â OF Eloy Jimenez, SP Dylan Cease, 1B Matt Rose, IF Bryant Flete traded to the Chicago White Sox for SP Jose Quintana.
The Aroldis Chapman-for-Gleyber Torres trade will be a popular talking point for years to come, but I still firmly believe the Chicago Cubs front office would make that trade 10 times out of 10 if the result is a World Series title.
Instead, we'll go with a recent summer blockbuster that didn't yield postseason glory.
Had Jose Quintana come aboard in 2017 and helped lead the Cubs to another World Series title, this trade would look like a solid move, albeit one that came at a steep price. Instead, he's posted a 4.23 ERA (102 ERA+) in two-and-a-half seasons with the team, and the Cubs have yet to return to the Fall Classic.
Meanwhile, Eloy Jimenez looked every bit the part of a future star when he posted a 117 OPS+ and slugged 31 home runs as a rookie last season. Despite his initial struggles at the MLB level, Dylan Cease also has a chance to be a long-term rotation piece on the South Side.
Runner-Up: 3B Josh Donaldson, OF Matt Murton, OF Eric Patterson, SP Sean Gallagher traded to the Oakland Athletics for SP Rich Harden, RP Chad Gaudin (July 8, 2008).
Chicago White Sox: Trading SS Fernando Tatis Jr.
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June 4, 2016: SS Fernando Tatis Jr., SP Erik Johnson traded to the San Diego Padres for SP James Shields, cash.
Rick Hahn has made some excellent transactions since moving into the general manager's seat in 2013, helping to position the Chicago White Sox for long-term success.
Unfortunately, this might be the trade for which he's remembered when all is said and done.
With the White Sox sitting at 29-26 and just 1.5 games back in the AL Central standings, veteran workhorse James Shields was acquired two months before the trade deadline in an effort to shore up the starting rotation.
Instead, he struggled to an ugly 6.77 ERA in 22 starts, and the White Sox finished 16.5 games back in the standings with a 78-84 record. All told, Shields pitched to a 5.31 ERA in 436 innings with the White Sox; he was in the second season of a four-year, $75 million deal at the time of the trade.
Tatis had yet to make his pro debut at the time of the trade after signing for $700,000 as part of the 2015 international class. He's now one of baseball's brightest young stars, posting 4.1 WAR in 84 games as a 20-year-old rookie.
Runner-Up: SS Marcus Semien, SP Chris Bassitt, C Josh Phegley, 1B Rangel Ravelo traded to the Oakland Athletics for SP Jeff Samardzija, RP Michael Ynoa (Dec. 9, 2014).
Cincinnati Reds: Extending SP Homer Bailey
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Feb. 19, 2014: SP Homer Bailey signed to a six-year, $105 million extension.
After five mediocre seasons, Homer Bailey strung together strong showings in 2012 and 2013 and turned that into a massive payday.
He went 24-22 with a 3.58 ERA (110 ERA+) while averaging 208 innings and 32 starts during that two-year stretch, tossing a pair of no-hitters along the way. Prior to that, he had a 4.89 ERA in 436 innings.
The 27-year-old was a year removed from free agency at the time of the extension, and he was no doubt motivated to get a deal done to avoid competing for attention in a free-agent class headlined by Max Scherzer and Jon Lester.
After a respectable 2014 season, the wheels fell off.
Tommy John surgery limited him to eight starts in 2015 and 2016, and he was never able to regain his form, going 9-27 with a 6.25 ERA over 46 starts from 2015 through 2018.
The Reds managed to unload him on the Los Angeles Dodgers prior to last season in a seven-player deal that sent Matt Kemp's bloated contract the other way, but the inclusion of prospects Jeter Downs and Josiah Gray in that trade already hurts.
When the dust settled on his extension, Bailey had been paid $77 million by the Reds in exchange for minus-1.5 WAR.
Runner-Up: 3B Edwin Encarnacion, SP Zach Stewart, RP Josh Roenicke traded to the Toronto Blue Jays for 3B Scott Rolen (July 31, 2009).
Cleveland Indians: Failing to Re-Sign Manny Ramirez
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2000-01 Offseason: Manny Ramirez turns down a seven-year, $119 million "final" offer.
The Boston Red Sox altered the course of their franchise history when they signed Manny Ramirez to an eight-year, $160 million deal prior to the 2001 season.
Could the Cleveland Indians have matched that offer?
The initial ask from Ramirez's agent was a 10-year, $200 million deal, which the Indians countered with a seven-year, $119 million proposal. That was the team's "final offer" from general manager John Hart, according to Jayson Stark of ESPN.
That hard-line stance backfired, and one of the most productive hitters in baseball history ended up walking for an additional year and an extra $3 million per season. Was that worth losing an all-time-great slugger?
The Indians won the AL Central in 2001 before stumbling through three straight losing seasons. The Red Sox reached the ALCS in 2003 and ascended to a World Series title in 2004 with Ramirez leading the way.
Runner-Up: 2B Brandon Phillips traded to the Cincinnati Reds for RP Jeff Stevens (April 7, 2006).
Colorado Rockies: Trading IF/OF Chone Figgins
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July 13, 2001: IF/OF Chone Figgins traded to the Anaheim Angels for OF Kimera Bartee.
The infamous Mike Hampton and Denny Neagle signings both ended in disaster, but at least the Colorado front office was taking a proactive approach to improving the club's pitching staff. That's more than can be said about the current brass.
Instead, the decision to flip a young Chone Figgins gets the nod.
Dan O'Dowd, the man in the general manager's seat who made that trade, talked about it regretfully years later.
"Figgins would have helped us, especially at Coors Field. He could play so many positions, and he could hit," O'Dowd told Thomas Harding of MLB.com in 2016. "That was a bad deal, man."
Figgins debuted in 2002 and was an everyday player by 2004. He posted 22.4 WAR in eight seasons with the Angels, hitting .291 with a .363 on-base percentage and 280 steals and earning a spot on the AL All-Star team in 2009.
Kimera Bartee went 0-for-15 with two walks and one RBI in 12 games for the Rockies following the trade, and he never played in the big leagues again.
Runner-Up:Â SP Denny Neagle (5/$51M) and Mike Hampton (8/$121M) signed in free agency (2000-01 offseason).
Detroit Tigers: Extending 1B Miguel Cabrera
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March 28, 2014: 1B Miguel Cabrera signed to an eight-year, $248 million extension.
Miguel Cabrera is a surefire Hall of Famer and one of the greatest right-handed hitters to ever set foot on a baseball field.
That didn't make this extension a good idea.
The 30-year-old was fresh off his third straight batting title and his second AL MVP win in a row, but he was also still under contract for two more years when he was handed this massive $248 million deal. Had the front office waited to pull the trigger on an extension, it would have seen the writing on the wall.
His slugging percentage dropped more than 100 points in 2014, and while he remained productive and even won another batting title in 2015, he was no longer the same Triple Crown threat.
The decline has been a steep one over the past three seasons with a 99 OPS+ and minus-0.3 WAR to show for 304 games, and he's still owed a staggering $124 million heading into 2020.
Runner-Up: 3B Eugenio Suarez, SP Jonathon Crawford traded to the Cincinnati Reds for SP Alfredo Simon (Dec. 11, 2014).
Houston Astros: Trading RP Josh Hader, SP Adrian Houser
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July 30, 2015: RP Josh Hader, SP Adrian Houser, OF Domingo Santana, OF Brett Phillips traded to the Milwaukee Brewers for OF Carlos Gomez, SP Mike Fiers, cash.
In pursuit of their first postseason appearance in a decade, the Houston Astros hoped Carlos Gomez would be the missing piece that pushed them over the top.
They ended up making the playoffs, but Gomez hit just .242/.288/.383 (85 OPS+) in 163 plate appearances, and he was released the following August.
Meanwhile, Josh Hader has emerged as baseball's most dominant reliever in Milwaukee, posting a 2.42 ERA and 0.85 WHIP with a staggering 349 strikeouts in 204.2 innings over three seasons. Do the Astros still make the poorly received Roberto Osuna trade if Hader is anchoring their bullpen?
Adrian Houser looks like a potential breakout candidate heading into 2020 and would have been a potential replacement for Gerrit Cole and Wade Miley in the rotation, Domingo Santana had a 30-homer season in 2017, and Brett Phillips was used to acquire Mike Moustakas at the 2018 deadline.
Not to be overlooked, but this trade also brought Mike Fiers into the Houston Astros locker room, where he became privy to certain information. That's all we'll say about that.
Runner-Up: 2B Ben Zobrist, SP Mitch Talbot traded to Tampa Bay Rays for IF/OF Aubrey Huff, cash (July 12, 2006).
Kansas City Royals: Not Getting More for CF Carlos Beltran
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June 24, 2004:Â CF Carlos Beltran traded in a three-team deal with the Houston Astros and Oakland Athletics for C John Buck, 3B Mark Teahen, SP Mike Wood, cash.
The Kansas City Royals were never going to re-sign Carlos Beltran. The issue here is the fact that they were not able to acquire a better return for their five-tool superstar.
Catcher John Buck was the No. 3 prospect in the Houston Astros system and ranked outside the top 100 prospects in baseball. He hit 70 home runs and posted 2.0 WAR in six seasons with the Royals.
Meanwhile, Mike Wood (No. 12) and Mark Teahen (No. 15) were not even ranked among the top 10 prospects in the Oakland system. Teahen was worth 4.0 WAR in five passable seasons in Kansas City, while Wood flopped as a starter and wound up posting 0.7 WAR in 87 total appearances over three years.
That's a grand total of 6.7 WAR for the best homegrown player the organization had seen since George Brett.
Had the Royals waited until closer to the deadline rather than pulling the trigger on a trade in June, they might have done better.
Runner-Up:Â 2B Omar Infante signed to a four-year, $30.25 million deal (Dec. 16, 2013).
Los Angeles Angels: Trading SP Mike Clevinger
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Aug. 24, 2014:Â SP Mike Clevinger traded to the Cleveland Indians for RP Vinnie Pestano.
The Albert Pujols or Josh Hamilton contracts would be the easy answer here. However, financial flexibility and offensive production have not been the issue for the Los Angeles Angels during their recent run of just one postseason appearance in 10 years.
A complete and utter lack of viable starting pitching has been the problem.
That's what makes the decision to trade a young Mike Clevinger such a regrettable oneâand the appropriate use of the team's mulligan.
At the time of the trade, Clevinger was a 23-year-old with a 5.37 ERA and 58 strikeouts in 55.1 High-A innings, and he wasn't much better immediately following the move.
The following year, he looked like a different pitcher, posting a 2.73 ERA and 1.06 WHIP with 145 strikeouts in 158 innings at Double-A to emerge as a legitimate prospect. He made his MLB debut on May 18, 2016, and in parts of four seasons, he's gone 41-21 with a 3.20 ERA (141 ERA+), 1.19 WHIP and 10.1 strikeouts per nine innings.
The 29-year-old is still under team control through the 2022 season, and he would be the ace of the Angels' staff if he were still around.
Runner-Up: RF Josh Hamilton signed to a five-year, $125 million deal (Dec. 15, 2012).
Los Angeles Dodgers: Trading OF Yordan Alvarez
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Aug. 1, 2016: OF Yordan Alvarez traded to the Houston Astros for RP Josh Fields.
The Los Angeles Dodgers have clung tightly to their top prospects in recent years, refusing to entertain trade offers that included guys like Joc Pederson, Corey Seager, Julio Urias, Cody Bellinger and Walker Buehler.
However, they let one slip through their fingers before he ever had a chance to establish himself when they traded Yordan Alvarez to the Houston Astros.
Just 47 days after he was signed to a $2 million bonus, Alvarez was traded for reliever Josh Fields.
To his credit, Fields posted a 2.79 ERA and 10.2 K/9 in 22 appearances following the trade and a 2.61 ERA with 2.0 WAR in 124 total games for the Dodgers.
Meanwhile, Alvarez emerged as one of the top offensive prospects in baseball, then he took the league by storm last season when he hit .313/.412/.655 with 26 doubles and 27 home runs in just 87 games to win AL Rookie of the Year honors.
The 22-year-old is now one of the brightest young stars in baseball, and all it cost the Astros to land him was a middle reliever they had taken in the Rule 5 draft a few years prior.
Runner-Up: C/1B Carlos Santana, RP Jon Meloan traded to the Cleveland Indians for 3B Casey Blake, cash (July 26, 2008).
Miami Marlins: Trading LF Christian Yelich
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Jan. 25, 2018: LF Christian Yelich traded to the Milwaukee Brewers for OF Lewis Brinson, OF Monte Harrison, 2B Isan Diaz, SP Jordan Yamamoto.
The Miami Marlins made the right decision blowing things up and rebuilding from the ground up. They just should have done that rebuilding around Christian Yelich rather than inexplicably trading him and his team-friendly contract for a lackluster return.
Flipping Giancarlo Stanton and his bloated contract made sense. The same goes for Marcell Ozuna two years removed from free agency when his value was at its peak.
However, Yelich was a cost-controlled asset coming off his fourth straight season of at least 3.5 WAR, and he was set to make $58.25 million over the next five seasons at the time of the trade.
The move defied logic.
All four players acquired in the deal still have a chance to be solid contributors in Miami, but Yelich is now one of the best players in baseball with an NL MVP Award on his mantle.
Runner-Up: SP Chris Paddack traded to the San Diego Padres for RP Fernando Rodney (June 30, 2016).
Milwaukee Brewers: Trading CF Lorenzo Cain, SP Jake Odorizzi, SS Alcides Escobar
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Dec. 19, 2010: CF Lorenzo Cain, SP Jake Odorizzi, SS Alcides Escobar, RP Jeremy Jeffress traded to the Kansas City Royals for SP Zack Greinke, SS Yuniesky Betancourt, cash.
Zack Greinke did his part in 2011, going 16-6 with a 3.83 ERA, 1.20 WHIP and 201 strikeouts in 171.2 innings. The Milwaukee Brewers won the NL Central and advanced to the NLCS.
They also managed to cut their losses the following season when they flipped him to the Los Angeles Angels for a package built around future All-Star shortstop Jean Segura.
Still, this was a ton to give up with no World Series title to show for it.
Lorenzo Cain and Alcides Escobar both emerged as key contributors for the Kansas City Royals teams that reached the World Series in 2014 and won it in 2015, while Jake Odorizzi was used to acquire James Shields and Wade Davis, who were also key cogs on those rosters.
Interestingly, Cain and reliever Jeremy Jeffress both made their way back to Milwaukee years later.
Runner-Up: OF Carlos Lee, OF Nelson Cruz traded to the Texas Rangers for OF Kevin Mench, RP Francisco Cordero, OF Laynce Nix, RP Julian Cordero (July 28, 2006).
Minnesota Twins: Non-Tendering DH David Ortiz
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Dec. 16, 2002: David Ortiz released by the Minnesota Twins.
Let's try to rationalize this one from the Minnesota Twins' perspective.
David Ortiz posted a 120 OPS+ with 20 home runs over 466 plate appearances in 2002, but he hit just .203 against left-handed pitching and was essentially relegated to platoon duties. After earning $950,000 that season, he was about to become more expensive for a budget-conscious Twins team.
Still, the decision to non-tender and eventually release him is hard to understand. Former teammate Torii Hunter spoke candidly about the team's decision while talking with Doug Miller of MLB.com in 2015:
"David always could hit. I still don't understand why the Twins non-tendered him. Now that I'm older, I'm really like, 'That was stupid.'
"The worst mistake [Twins general manager] Terry Ryan ever made was to non-tender David Ortiz. Boston got a diamond in the rough in 2003 and gave him a shot. He led those boys to the World Series championship. David Ortiz turned that franchise around. They might not say it, but I saw it."
Ortiz went on to launch 483 home runs and win three World Series titles over 14 seasons in Boston.
Runner-Up: SP Matt Garza, SS Jason Bartlett, RP Eddie Morlan traded to the Tampa Bay Rays for OF Delmon Young, IF Brendan Harris, OF Jason Pridie (Nov. 28, 2007).
New York Mets: Re-Signing LF Yoenis Cespedes
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Nov. 30, 2016:Â OF Yoenis Cespedes re-signed to a four-year, $110 million deal.
A few years from now, if Jarred Kelenic develops into the type of perennial All-Star many expect him to be for the Seattle Mariners, last offseason's Robinson Cano/Edwin Diaz blockbuster could be the slam-dunk answer here.
For now, we'll go with the contract Yoenis Cespedes signed after opting out of the final two years and $47.5 million of his previous deal with the New York Mets.
At the time, Cespedes was coming off a stellar 2016 season in which he posted a 136 OPS+ with 31 home runs to win Silver Slugger honors and finish eighth in NL MVP voting.
However, he's played in just 119 games since agreeing to that new contract, including a lost 2019 season that he spent recovering from a fractured ankle he suffered working on his ranch in the offseason.
The Mets have managed to recoup some of their money with his 2020 salary slashed to $6 million as part of a restructured deal, but they would no doubt avoid this signing altogether if given the chance.
Runner-Up:Â 3B Justin Turner non-tendered (Dec. 2, 2013).
New York Yankees: Signing CF Jacoby Ellsbury
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Dec. 7, 2013: CF Jacoby Ellsbury signed to a seven-year, $153 million deal.
Giancarlo Stanton is owed $244 million over the next eight years, and while $50 million of that will be paid by the Miami Marlins, that's still a considerable chunk of change for a guy who played all of 18 games last year.
That said, he's still just 30 years old and one season removed from a 38-homer, 100-RBI showing.
So for now, the nod goes to the Jacoby Ellsbury contract, which is still on the books for 2020.
After posting a lackluster 95 OPS+ and 9.7 WAR over the first four seasons of his seven-year deal, Ellsbury spent the past two campaigns watching from the sidelines with hip and shoulder injuries, among other ailments.
The Yankees finally bit the bullet and released him on Nov. 20, 2019, absorbing the $21.1 million he was owed in 2020 and a $5 million buyout on a 2021 club option.
Runner-Up: SP Jose Quintana granted MiLB free agency (Nov. 2, 2011).
Oakland Athletics: Trading 3B Josh Donaldson
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Nov. 28, 2014: 3B Josh Donaldson traded to the Toronto Blue Jays for 3B Brett Lawrie, SS Franklin Barreto, SP Kendall Graveman, SP Sean Nolin.
It makes perfect sense for a small-market team to flip a star player when free agency is fast approaching and it's unlikely he's going to stick around. It made zero sense for the Oakland Athletics to trade Josh Donaldson after back-to-back top-10 finishes in AL MVP voting when he had four years of club control remaining.
Even if Brett Lawrie had proved a serviceable replacement at third base and Franklin Barreto had developed as hoped, it would still have been hard to justify trading one of the best all-around players of the last 20 years.Â
Donaldson won AL MVP in his first season with the Toronto Blue Jays and went on to rack up 18.9 WAR in his three full years with the team.
The four players Oakland acquired have thus far provided a combined 6.4 WAR for the team, with the bulk of that coming from Kendall Graveman (5.5).
Runner-Up:Â IF Max Muncy released (March 31, 2017).
Philadelphia Phillies: Trading SPs Gavin Floyd, Gio Gonzalez
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Dec. 6, 2006: SP Gio Gonzalez, SP Gavin Floyd traded to the Chicago White Sox for SP Freddy Garcia.
The Philadelphia Phillies thought they were giving their starting rotation a shot in the arm when they acquired Freddy Garcia from the Chicago White Sox on the heels of a 17-win season.
Instead, he dealt with shoulder issues early in the year and went just 1-5 with a 5.90 ERA and 1.60 WHIP in 58 innings before hitting free agency.
After a rocky first season of his own in Chicago, former top prospect Gavin Floyd emerged as a staple in the White Sox rotation. From 2008 through 2012, he went 62-56 with a 4.12 ERA (108 ERA+) and 15.9 WAR, averaging 190 innings and 31 starts per season.
He would have been a useful piece of the puzzle in Philadelphia during the team's five straight trips to the playoffs.
Gio Gonzalez was traded again a year later in the deal that sent Nick Swisher from Oakland to Chicago, and he was still pitching in 2019 with 130 career wins, 1,826 strikeouts and 14.0 WAR under his belt.
Runner-Up: 1B Ryan Howard signed to a five-year, $125 million extension (April 26, 2010).
Pittsburgh Pirates: Trading OF Austin Meadows, SP Tyler Glasnow
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July 31, 2018:Â SP Tyler Glasnow, OF Austin Meadows, SP Shane Baz traded to the Tampa Bay Rays for SP Chris Archer.
The Pittsburgh Pirates were 56-52 and in third place in the NL Central standings when they pulled off an unexpected blockbuster trade to acquire Chris Archer at the 2018 deadline.
The team was riding a 16-4 hot streak that had thrust it into wild-card contention. Even if it fell short, Archer's remaining club control would make him a key addition to the 2019 plans, as well.
Fast forward and the Pirates missed the playoffs in 2018 before taking a precipitous fall down the standings with a 69-93 record last year.
Archer had a 5.19 ERA over 119.2 innings in his first full season with the Pirates, and there was some question about whether his team-friendly $9 million option for 2020 would even be exercised. He's controllable through 2021 with an $11 million option.
On the other side, Austin Meadows emerged as an All-Star, posting a 143 OPS+ while leading the Tampa Bay Rays with 33 home runs in a 4.0-WAR season. Tyler Glasnow was equally impressive early on, going 6-1 with a 1.78 ERA and 76 strikeouts in 60.2 innings over 12 starts before a forearm strain prematurely ended his season.
Not to be overlooked, right-hander Shane Baz will begin the 2020 season as the No. 3 prospect in the Tampa Bay system and the No. 71 prospect in baseball, according to Baseball America.
This one is going to sting for a while.
Runner-Up: SP Jason Schmidt, OF John Vander Wal traded to the San Francisco Giants for SP Ryan Vogelsong, OF Armando Rios (July 30, 2001).
San Diego Padres: Trading 1B Anthony Rizzo
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Jan. 6, 2012: 1B Anthony Rizzo, RP Zach Cates traded to the Chicago Cubs for SP Andrew Cashner, OF Kyung-Min Na.
In a bubble, the decision to trade Anthony Rizzo for Andrew Cashner hurts.
Rizzo has developed into a franchise cornerstone with the Chicago Cubs, averaging 30 home runs and 99 RBI over the past six seasons while racking up 33.9 WAR in his time with the North Siders.
Cashner posted a 98 ERA+ in 608.2 innings with the Padres before he was traded to the Miami Marlins in a deal that brought back Josh Naylor. His five-year stint in San Diego was worth 3.2 WAR.
However, the impact of this one stretches beyond just the players involved in the 2012 trade.
If Rizzo were still wearing a Padres uniform, the front office might not have felt compelled to throw an absurd eight-year, $144 million contract at Eric Hosmer in free agency.
Runner-Up: SP Corey Kluber traded to the Cleveland Indians for OF Ryan Ludwick in three-team, four-player deal (July 31, 2010).
San Francisco Giants: Trading SP Luis Castillo
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Dec. 20, 2014: SP Luis Castillo, SP Kendry Flores traded to the Miami Marlins for 3B Casey McGehee.
How good would Luis Castillo look at the center of the San Francisco Giants' current rebuilding plans?
The 27-year-old is still under team control through the 2023 season, and he emerged as one of the best pitchers in baseball last season, going 15-8 with a 3.40 ERA, 1.14 WHIP and 226 strikeouts in 190.2 innings for the Cincinnati Reds.
At the time of this trade with the Marlins, he was still a raw 22-year-old who had just shown flashes at Single-A with a 3.07 ERA and 66 strikeouts in 58.2 innings.
Kendry Flores was actually the more highly regarded prospect at the time, slotting in at No. 5 in the Marlins system following the trade, according to Baseball America.
Casey McGehee, who was acquired to replace Pablo Sandoval at the hot corner, hit .213 with a 59 OPS+ in 138 plate appearances before he was released on July 8 to clear the way for Matt Duffy's breakout rookie season. He ended up re-signing with the Marlins two days after he was released, which means Castillo was essentially acquired for free.
Runner-Up: SP Francisco Liriano, RP Joe Nathan, SP Boof Bonser traded to the Minnesota Twins for C A.J. Pierzynski (Nov. 14, 2003).
Seattle Mariners: Trading CF Adam Jones, SP Chris Tillman
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Feb. 8, 2008: CF Adam Jones, SP Chris Tillman, RP George Sherrill, RP Kam Mickolio, SP Tony Butler traded to the Baltimore Orioles for SP Erik Bedard.
Erik Bedard went 13-5 with a 3.16 ERA, 1.09 WHIP and 221 strikeouts in 182 innings during the 2007 season to lead the AL in K/9 (10.9) and finish fifth in AL Cy Young voting.
Two years removed from free agency, the Baltimore Orioles decided to sell high on the southpaw. That brought back a solid prospect haul:
- SP Chris Tillman: No. 3 SEA prospect, No. 67 MLB prospect
- SP Tony Butler: No. 12 SEA prospect
- RP Kam Mickolio: No. 18 SEA prospect
That said, the centerpiece of the deal was center fielder Adam Jones. He had been the No. 1 prospect in the Seattle system and the No. 28 prospect in baseball heading into 2007 before he exhausted his rookie eligibility.
Jones went on to make five All-Star appearances and post 32.2 WAR with the Orioles. Tillman was an All-Star in 2013 and made three Opening Day starts, and reliever George Sherrill saved 51 games in two seasons and made an All-Star team in 2008.
Bedard continued to pitch well in Seattle when healthy, but he was limited to just 30 starts over the two years following the trade.
Runner-Up: OF Shin-Soo Choo, SP Shawn Nottingham traded to the Cleveland Indians for 1B Ben Broussard (July 26, 2006).
St. Louis Cardinals: Trading SP Dan Haren
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Dec. 18, 2004: SP Dan Haren, RP Kiko Calero, 1B Daric Barton traded to the Oakland Athletics for SP Mark Mulder.
Two days after trading Tim Hudson for a less-than-impressive return, the Oakland Athletics fleeced the St. Louis Cardinals when they shipped out another member of their once-vaunted "Big Three" starters.
Mark Mulder went 16-8 with a 3.64 ERA in 205 innings during his first season in St. Louis but ended up making just 23 more appearances after that, struggling to a 7.73 ERA in 106 innings while battling a rotator cuff injury and subsequent setbacks.
In return, the Cardinals shipped out promising young starter Dan Haren, who went 43-34 with a 3.64 ERA (120 ERA+) and 11.4 WAR in three seasons with the A's before he was traded to the Diamondbacks in another blockbuster deal.
Reliever Kiko Calero (179 G, 3.96 ERA, 1.8 WAR) and first baseman Daric Barton (551 G, 99 OPS+, 8.9 WAR) were also solid contributors during their time in Oakland.
Runner-Up: OF Dexter Fowler signed to a five-year, $82.5 million deal (Dec. 9, 2016).
Tampa Bay Rays: Trading SP German Marquez
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Jan. 28, 2016: SP German Marquez, RP Jake McGee traded to the Colorado Rockies for OF Corey Dickerson, 3B Kevin Padlo.
The Tampa Bay Rays have been as good as any franchise at identifying and developing pitching talent in recent years, but German Marquez stands out as the one who got away.
The 25-year-old has been quietly excellent in his three full seasons as a member of the Colorado Rockies rotation, posting a 116 ERA+ with 552 strikeouts in 532 innings and 11.2 WAR.
His breakout 2018 season earned him a five-year, $43 million extension, and he looks like one of the few viable long-term pieces in Colorado.
Corey Dickerson had two solid seasons in Tampa Bay, even making an All-Star team in 2017 before he was surprisingly non-tendered. His time with the Rays was worth a modest 4.4 WAR.
Third baseman Kevin Padlo enters the 2020 season as the No. 17 prospect in the Tampa Bay system, per Baseball America, after he posted a .927 OPS with 31 doubles and 21 home runs between Double-A and Triple-A.
The 23-year-old has his work cut out for him to even the scales on this trade.
Runner-Up: OF Josh Hamilton left unprotected in the Rule 5 draft (Dec. 7, 2006).
Texas Rangers: Not Acquiring 2B Robinson Cano in the Alex Rodriguez Trade
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April 23, 2004: Choosing SS Joaquin Arias instead of 2B Robinson Cano as the second piece in the Alex Rodriguez-for-Alfonso Soriano swap with the New York Yankees.
In the years since the epic Alex Rodriguez-for-Alfonso Soriano blockbuster trade was completed, it has come to light that the Texas Rangers could have also had Robinson Cano in that trade.
Let's set the scene.
"Soriano was the featured player that they wanted to move," then-Rangers general manager John Hart told reporters. "And we went through a laundry list of five or six players of which we would end up taking a young shortstop, Joaquin Arias."
Yankees general manager Brian Cashman confirmed, saying, "There was another player sitting on that list, thankfully, [that] they passed up, which was Robbie Cano."
Yikes.
Arias was the No. 4 prospect in the Yankees system at the time, while Cano checked in at No. 6, per Baseball America. So there's that.
Runner-Up: SP Kyle Hendricks, 3B Christian Villanueva traded to the Chicago Cubs for SP Ryan Dempster (July 31, 2012).
Toronto Blue Jays: Trading SP Noah Syndergaard
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Dec. 17, 2012: SP Noah Syndergaard, C Travis d'Arnaud, OF Wuilmer Becerra, C John Buck traded to the New York Mets for SP R.A. Dickey, C Josh Thole, C Mike Nickeas.
This trade was the definition of selling high on the part of the New York Mets.
R.A. Dickey resurrected his career in 2010 and won NL Cy Young honors two years later when he went 20-6 with a 2.73 ERA, 1.05 WHIP and 230 strikeouts in 233.2 innings.
He was 37 years old.
Despite his age and limited track record, the Blue Jays traded their top two prospects in catcher Travis d'Arnaud (No. 23 MLB prospect) and right-hander Noah Syndergaard (No. 54 MLB prospect) to add him to their rotation.
The knuckleballer continued to eat up innings over his four seasons in Toronto, averaging 32 starts and 206 frames, but he never matched his 2012 level of success with a 4.05 ERA and 100 ERA+.
While d'Arnaud never developed into the franchise catcher he was expected to be, he did post a respectable 94 OPS+ and 2.1 WAR in 407 games.
The obvious price here was Syndergaard, who has been one of the most overpowering pitchers in baseball when healthy.
Runner-Up: IF Michael Young, RP Darwin Cubillan traded to the Texas Rangers for SP Esteban Loaiza (July 19, 2000).
Washington Nationals: Trading SP Lucas Giolito
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Dec. 7, 2016: SP Lucas Giolito, SP Reynaldo Lopez, SP Dane Dunning traded to the Chicago White Sox for RF Adam Eaton.
The Bartolo Colon blockbuster will always have a place in lopsided trade lore. However, the repercussions of trading Lucas Giolito could be felt by the Washington Nationals for years to come.
The 25-year-old took his lumps in 2018 and came out the other side as one of the best pitchers in the American League, going 14-9 with a 3.41 ERA, 1.06 WHIP and 228 strikeouts in 176.2 innings to finish sixth in AL Cy Young voting last year.
If the Nationals had put their faith in the 2012 first-round pick, maybe they wouldn't have needed to throw $140 million at Patrick Corbin in free agency, and maybe then they would have had enough money to re-sign both Stephen Strasburg and Anthony Rendon this offseason rather than having to let Rendon walk.
Just a thought.
Adam Eaton was coming off a 6.6-WAR season at the time of the trade, but he's been worth just 2.9 WAR in three seasons with the Nationals.
Also, despite his 5.38 ERA in 184 innings last year, don't sleep on Reynaldo Lopez. He's still just 26 and has the stuff to develop into an impact starter.
Runner-Up:Â CF Grady Sizemore, SP Cliff Lee, 2B Brandon Phillips, 1B Lee Stevens traded to the Cleveland Indians for SP Bartolo Colon, SP Tim Drew (June 27, 2002).
All stats courtesy of Baseball Reference and FanGraphs, unless otherwise noted.
