There's undeniable risk when it comes to pulling the trigger on a blockbuster deal at the trade deadline.

Even after he helped them win a World Series, fans around the league still question the Chicago Cubs' decision to trade Gleyber Torres for two months of flamethrowing closer Aroldis Chapman.

The Texas Rangers made back-to-back World Series appearances thanks at least in part to the haul of prospect talent they acquired when they traded slugger Mark Teixeira to the Atlanta Braves, while the Braves found themselves mired in a lengthy rebuild a few short years after that trade.

We set out to find the most regrettable deadline deals of the past 10 years. If baseball teams got a mulligan, they'd use them on these deals in a heartbeat.

While it's still too soon to tell who will come out on top in these trades, here are a couple of deals from last year that could eventually join this list:

7/13/2017: CWS traded LHP Jose Quintana to CHC for OF Eloy Jimenez, RHP Dylan Cease, IF Bryant Flete, 3B Matt Rose



7/16/2017: OAK traded RHP Ryan Madson, LHP Sean Doolittle to WAS for RHP Blake Treinen, LHP Jesus Luzardo, 3B Sheldon Neuse

Now, let's kick things off with some honorable mentions before diving into the seven most brutal blockbuster trade fails of the past 10 years.

The trades are ranked based on a combination of lopsidedness and the production and impact the key player in each deal had on his team's success, particularly in the postseason.

Honorable Mentions

Adam Duvall Joe Robbins/Getty Images

7/30/2009: PIT acquired 2B Josh Harrison , RHP Kevin Hart, RHP Jose Ascanio from CHC for LHP Tom Gorzelanny, LHP John Grabow

PIT acquired , RHP Kevin Hart, RHP Jose Ascanio from CHC for LHP Tom Gorzelanny, LHP John Grabow 7/29/2010: WAS acquired C Wilson Ramos , LHP Joe Testa from MIN for RHP Matt Capps

WAS acquired , LHP Joe Testa from MIN for RHP Matt Capps 7/30/2010: WAS acquired RHP Tanner Roark , RHP Ryan Tatusko from TEX for IF Christian Guzman

WAS acquired , RHP Ryan Tatusko from TEX for IF Christian Guzman 7/30/2011: DET acquired RHP Doug Fister , RHP David Pauley from SEA for LHP Charlie Furbush, OF Casper Wells, 3B Francisco Martinez, RHP Chance Ruffin

DET acquired , RHP David Pauley from SEA for LHP Charlie Furbush, OF Casper Wells, 3B Francisco Martinez, RHP Chance Ruffin 7/30/2011: BAL acquired 1B Chris Davis , RHP Tommy Hunter from TEX for RHP Koji Uehara

BAL acquired , from TEX for RHP Koji Uehara 7/21/2012: HOU acquired RHP Chris Devenski , LHP Blair Walters, RHP Matt Heidenreich from CWS for RHP Brett Myers

HOU acquired , LHP Blair Walters, RHP Matt Heidenreich from CWS for RHP Brett Myers 7/25/2012: LAD acquired SS Hanley Ramirez , LHP Randy Choate from MIA for RHP Nathan Eovaldi, RHP Scott McGough

LAD acquired , LHP Randy Choate from MIA for RHP Nathan Eovaldi, RHP Scott McGough 7/28/2012: MIN acquired 3B Eduardo Escobar , LHP Pedro Hernandez from CWS for LHP Francisco Liriano

MIN acquired , LHP Pedro Hernandez from CWS for LHP Francisco Liriano 7/22/2013: CHC acquired RHP Carl Edwards Jr. , RHP Justin Grimm, 3B Mike Olt, RHP Neil Ramirez for RHP Matt Garza

CHC acquired , RHP Justin Grimm, 3B Mike Olt, RHP Neil Ramirez for RHP Matt Garza 7/31/2014: ARI acquired OF Mitch Haniger , LHP Anthony Banda from MIL for OF Gerardo Parra

ARI acquired , from MIL for OF Gerardo Parra 7/30/2015: CIN acquired OF Adam Duvall , RHP Keury Mella from SF for RHP Mike Leake

CIN acquired , RHP Keury Mella from SF for RHP Mike Leake 7/14/2016: BOS acquired LHP Drew Pomeranz from SD for RHP Anderson Espinoza

BOS acquired from SD for RHP Anderson Espinoza 7/30/2016: PIT acquired LHP Felipe Vazquez, LHP Taylor Hearn from WAS for RHP Mark Melancon

7. Los Angeles Dodgers Acquire Alex Wood

Alex Wood Rob Leiter/Getty Images

Date: July 30, 2015

To LAD: LHP Alex Wood, RHP Bronson Arroyo, LHP Luis Avilan, RHP Jim Johnson, SS Jose Peraza, RHP Mat Latos, OF Mike Morse

To ATL: 3B Hector Olivera, LHP Paco Rodriguez, RHP Zachary Bird, No. 40 overall pick in 2016 (LHP Joey Wentz)

To MIA: RHP Victor Araujo, RHP Jeff Brigham, RHP Kevin Guzman

Overview

This 14-player deal still has a chance to look a bit better from the Atlanta Braves' standpoint if Joey Wentz develops into a long-term rotation piece.

For now, the Los Angeles Dodgers are the clear winner.

They dealt Hector Olivera just four months after signing him to a six-year, $62.5 million contract. That turned out to be a stroke of brilliance, as the Cuban standout went on to post a minus-0.2 WAR over 108 plate appearances with the Braves before he was flipped for the contract of Matt Kemp in 2016 and subsequently released.

In the process, they picked up three-and-a-half years of Alex Wood, who has gone 27-18 with a 3.48 ERA and 1.15 WHIP in 65 starts so far since joining the Dodgers. He finished ninth in National League Cy Young voting last year and earned his first trip to the All-Star Game.

Lefty reliever Luis Avilan (111 G, 22 HLD, 3.43 ERA, 10.8 K/9) was a productive piece in Los Angeles as well.

The Miami Marlins also grade out as losers. They gave up the No. 40 overall pick in 2016, which turned out to be Wentz, in exchange for three lower-level prospects and the ability to unload the contracts of Mat Latos and Mike Morse.

6. Milwaukee Brewers Acquire Josh Hader and Domingo Santana

Josh Hader Dylan Buell/Getty Images

Date: July 30, 2015

To MIL: LHP Josh Hader, OF Domingo Santana, OF Brett Phillips, RHP Adrian Houser

To HOU: CF Carlos Gomez, SP Mike Fiers, cash

Overview

A truly dynamic talent during his peak with the Milwaukee Brewers, center fielder Carlos Gomez racked up 12.4 WAR in 2013 and 2014 before his production dropped off significantly during an injury-plagued 2015 campaign.

He was hitting .262/.328/.423 with a 1.6 WAR when the Brewers packaged him with starter Mike Fiers and shipped him to Houston in exchange for four prospects.

Gomez wound up hitting a brutal .221/.277/.342 over 126 games with the Astros before he was eventually released on Aug. 18, 2016. The Texas Rangers scooped him up two days later, and he ended up resurrecting his career, but he produced next to nothing during his time in Houston.

Fiers went 21-19 with a 4.59 ERA (86 ERA+) in 384.1 innings of work with the Astros before joining the Detroit Tigers in free agency this past winter.

In exchange for that duo, the Brewers picked up a pitcher in Josh Hader who has quickly emerged as one of the game's most dominant relievers.

The 24-year-old sports a 1.82 ERA, 0.90 WHIP and a staggering 153 strikeouts in 94 innings since debuting last season, including a 1.55 ERA and 16.5 K/9 in 30 games this season to earn a spot on the NL All-Star team.

Domingo Santana posted a 125 OPS+ with 30 home runs last season, but he's fallen victim to an outfield logjam this year, while Brett Phillips (No. 5) and Adrian Houser (No. 12) still rank among the team's top prospects, according to MLB.com.

5. Chicago Cubs Acquire Addison Russell

Addison Russell Kirk Irwin/Getty Images

Date: July 5, 2014

To CHC: SS Addison Russell, OF Billy McKinney, RHP Dan Straily, cash

To OAK: RHP Jeff Samardzija, RHP Jason Hammel

Overview

The Oakland Athletics had the best record in baseball (53-33) on July 4, 2014, but they needed some rotation help behind the one-two punch of Sonny Gray and Scott Kazmir if they were going to make a legitimate title run.

They found a willing seller in the rebuilding Chicago Cubs, who dealt Jeff Samardzija (17 GS, 2-7, 2.83 ERA, 1.20 WHIP) and Jason Hammel (17 GS, 8-5, 2.98 ERA, 1.02 WHIP) for a package built around top prospect Addison Russell.

No one would have questioned this deal if the A's had kept rolling and made it to the World Series.

Instead, they stumbled to a 35-41 record the rest of the way, falling to the AL Wild Card Game in the process, where they were eliminated by the Kansas City Royals in a 12-inning thriller.

Samardzija was traded to the Chicago White Sox during the offseason, Hammel ended up rejoining the Cubs in free agency and Oakland has not posted a winning record since.

Giving up Russell has proved to be a steep price to pay for an Oakland team that values cost-controlled young talent.

The No. 14 prospect in baseball heading into the 2014 season, according to Baseball America, Russell has racked up 12.6 WAR since debuting. He played a pivotal role in the team's 2016 World Series title and is undoubtedly one of the top defensive players in baseball, even if his offensive game has not progressed as hoped.

McKinney was later used in the trade to acquire Aroldis Chapman, and the Cubs bailed on Dan Straily sooner than they should have, but this deal still ranks as a major win for the North Siders.

4. Oakland Athletics Acquire 3B Josh Donaldson

Marcio Jose Sanchez/Associated Press

Date: July 8, 2008

To OAK: 3B Josh Donaldson, OF Matt Murton, RHP Sean Gallagher, OF Eric Patterson

To CHC: RHP Rich Harden, RHP Chad Gaudin

Overview

In the Chicago Cubs' defense, this trade looked like an excellent move at the time.

Rich Harden joined a contender and went 5-1 with a 1.77 ERA and 89 strikeouts in 71 innings over 12 starts down the stretch to help the Cubs reach the postseason.

He was 9-9 with a 4.09 ERA and 171 strikeouts in 141 innings the following season before departing in free agency, but it still looked like a solid trade.

Then, the 2013 season changed everything.

A 27-year-old Josh Donaldson came out of nowhere to hit .301/.384/.499 with 24 home runs and 93 RBI to finish fourth in AL MVP voting, a season that would prove to be the first step in his rapid ascent to superstardom.

His 36.7 WAR since the start of the 2013 season trails only Mike Trout (50.1) among all position players during that span, and he won AL MVP honors in 2015.

Of course, the Cubs wound up drafting an MVP third baseman of their own, but it's still an extremely lopsided move in hindsight.

3. Chicago Cubs Acquire Kyle Hendricks

Joe Robbins/Getty Images

Date: July 31, 2012

To TEX: RHP Ryan Dempster

To CHC: RHP Kyle Hendricks, 3B Christian Villanueva

Overview

If only the Los Angeles Dodgers had been willing to trade pitching prospect Allen Webster back in 2012, recent Chicago Cubs history might look decidedly different.

Ryan Dempster was the top rental arm on the trade market that year, and he had full veto power with 10-and-5 rights. He had made it clear the Dodgers were his preferred destination, but Los Angeles refused to include Webster—one of its top prospects at the time.

He wound up traded to the Texas Rangers instead, with the Cubs bringing back well-regarded third base prospect Christian Villanueva and a High-A starter by the name of Kyle Hendricks.

Six years later, Hendricks has established himself as a Cubs legend.

He threw a gem in Game 6 of the 2016 NLCS (7.1 IP, 2 H, 0 ER) and also earned the start in Game 7 of the World Series (4.2 IP, 4 H, 1 ER)—arguably the two biggest games in franchise history.

All told, the 28-year-old control artist is 43-30 with a 3.09 ERA, 1.12 WHIP and 14.2 WAR during his time with the Cubs, and he still has team control remaining through the 2020 season.



Dempster went 7-3 with a 5.09 ERA in 12 starts for a Rangers team that wound up losing in the Wild Card Game, before departing in free agency.

2. Chicago Cubs Aquire Jake Arrieta and Pedro Strop

Jonathan Daniel/Getty Images

Date: July 2, 2013

To CHC: RHP Jake Arrieta, RHP Pedro Strop, cash

To BAL: RHP Scott Feldman, C Steve Clevenger

Overview

The Chicago Cubs don't win the World Series without Jake Arrieta; team president Theo Epstein made that clear while talking with reporters this past offseason:

"None of us have rings without Jake Arrieta. He was as instrumental as anybody in the turnaround of this franchise. He helped lift the culture with the way he approached things. He won a ton of big games for us. We’re all huge fans of his. We wish him well. We wish his family well. Whatever team lands him in free agency is going to be getting a great pitcher and a great representative for the organization."

A top prospect during his time in the Baltimore system, Arrieta went 20-25 with a 5.46 ERA and 1.47 WHIP in 69 games (63 starts) over parts of four seasons with the big league club.

The change of scenery gave him a chance to get back to basics with his mechanics, and he was no longer looking over his shoulder after shuffling between Triple-A and the big leagues for much of his time in Baltimore.

He went 10-5 with a 2.53 ERA in 25 starts in his first full season in Chicago, and the following year, he won NL Cy Young honors with a second half for the ages (15 starts, 12-1, 0.75 ERA, 0.73 WHIP).

Aside from his regular-season success, he also went 5-3 with a 3.08 ERA and 1.08 WHIP in nine postseason starts, including 2-0 with a 2.38 ERA in his two World Series appearances in 2016.

Not to be overlooked, reliever Pedro Strop has also been an excellent addition. He's posted a 2.69 ERA, 1.04 WHIP and 10.4 K/9 in 338 appearances in Chicago while tallying 112 holds and eight saves.

And all for free-agent flier Scott Feldman.

The veteran signed a one-year, $6 million deal to join the Cubs and went 7-6 with a 3.46 ERA and 1.14 WHIP in 15 starts prior to the trade. He signed with the Houston Astros in free agency after the season.

1. Cleveland Indians Acquire Corey Kluber

Jason Miller/Getty Images

Date: July 31, 2010

To CLE: RHP Corey Kluber

To STL: RHP Jake Westbrook, LHP Nick Greenwood

To SD: OF Ryan Ludwick

Overview

The Jake Westbrook-for-Ryan Ludwick swap was the meat and potatoes of this deal at the time.

Westbrook went 4-4 with a 3.48 ERA in 12 starts with the Cardinals down the stretch and then re-signed on a two-year, $16.5 million deal as he helped the team win a World Series in 2011.

Ludwick racked up 59 home runs and 210 RBI in the two seasons prior to the trade, and he was hitting .281/.343/.484 with 11 home runs and 43 RBI at the time of the deal, but he did little of note in San Diego.

That said, it's Corey Kluber who has made this deal one to remember. Or forget, depending on your rooting interests.

Kluber was in Double-A at the time of the trade, and he had shown swing-and-miss stuff in the Padres system since going in the fourth round of the 2007 draft—albeit with mixed results from a peripheral standpoint.

He made his MLB debut in 2011 and started 12 games in 2012, when he posted a 5.14 ERA and 1.49 WHIP before carving out a regular rotation spot in 2013. He went 11-5 with a 3.85 ERA, 1.26 WHIP and 136 strikeouts in 147.1 innings that year, and that proved to be just the tip of the iceberg.

A breakout 2014 season earned him AL Cy Young honors, and he's gone 75-42 with a 2.79 ERA, 1.00 WHIP and 1,129 strikeouts in 1,002.2 innings since the start of that breakout campaign, including taking home another Cy Young award last season.

Throw in his 1.83 ERA in six starts during Cleveland's run to the 2016 World Series, and there's little question he's one of the best pitchers in the game today.

Jake Arrieta may have made a more profound impact in the Cubs organization, but in terms of sheer lopsidedness, the Kluber deal takes the No. 1 spot.

All stats courtesy of Baseball Reference and FanGraphs unless otherwise noted.