Commentary

Dealing an ace can be a crapshoot

A look back at blockbuster trades since 2000 involving big-name starters

Updated: July 23, 2009, 12:29 PM ET
By Jerry Crasnick | ESPN.com

Toronto general manager J.P. Ricciardi has the commodity that every team wants. Now we'll see if he can parlay all that phone time into something tangible.

As the Roy Halladay sweepstakes enters the final week, Ricciardi must decide whether to squeeze the trigger or hang onto his staff ace until the offseason. From here until Ricciardi's self-imposed July 28 deadline, it's all about guts, leverage, timing and sensing the desperation in the voice at the other end of the line.

As recent history shows, an ace pitcher on the trade block can bring a mother lode of talent in return, or a bunch of prospects who are long on hype and short on ability. The GM with the biggest chip has to rely on his scouts, make the deal and then wish for the best.

This week's edition of Starting 9 provides a little history lesson, as we focus on nine major trades since 2000 with a star pitcher as the featured attraction.

What kind of package can an ace bring in return? As the results show, not all blockbusters are created equal.

Bartolo Colon
Colon

The Bartolo Colon trade (June 2002)

The deal: The Indians send Colon and Tim Drew to Montreal for Cliff Lee, Grady Sizemore, Brandon Phillips and Lee Stevens.

The backdrop: Cleveland general manager Mark Shapiro, forced to shed payroll by owner Larry Dolan, sends his staff ace to Montreal for three prospects. The surprising Expos are 6½ games behind Atlanta in the National League East, and GM Omar Minaya is in a mood to go for it.

The initial reaction: Cleveland fans are ready to revolt. The Akron Beacon Journal runs a headline reading, "Colon trade a slap in face to fans; Shapiro talks about rebuilding team, but wrecking ball whisks Tribe's top pitcher to Montreal."

Minaya, in hindsight, says he made the deal because he was convinced the Expos were about to be contracted. That's a bit of a stretch, but Minaya is clearly under pressure to win now. He is generally hailed for his bold stroke: The Montreal Gazette headline reads, "Minaya works some magic," and a local columnist refers to Minaya as "brilliant"

Cleveland's grade: A. In Sizemore's first four seasons as an Indian, he made three All-Star teams, won two Gold Gloves and a Silver Slugger Award, and averaged 116 runs, and Lee went 81-48 with a Cy Young Award. The Indians might get an A-plus if they hadn't given up too early on Phillips and packed him off to Cincinnati.

Erik Bedard
Bedard

The Erik Bedard trade (February 2008)

The deal: Baltimore GM Andy MacPhail sends Bedard to Seattle for outfielder Adam Jones and pitchers George Sherrill, Chris Tillman, Kam Mickolio and Tony Butler.

The backdrop: Seattle is coming off an 88-win season, and GM Bill Bavasi bets the ranch that Bedard can help the Mariners make the playoffs for the first time since 2001. The rotation of Bedard, Felix Hernandez, Carlos Silva, Jarrod Washburn and Miguel Batista looks formidable on paper.

The initial reaction: The diehards at the USS Mariner blog like Bedard, but hate the trade because Seattle surrendered a potential superstar in Jones and helped replenish Baltimore's farm system. Derek Zumsteg calls it a "crappy deal" and writes, "It makes me want to throw up in my M's cap. And then mail the cap to the team."

Baltimore's grade: A. Jones made the All-Star team this year at age 23. Sherrill has 51 saves in a season and a half, and Tillman, 21, has 95 strikeouts in 93 innings with Triple-A Norfolk this season.

Bedard, in contrast, helped cost Bavasi and manager John McLaren their jobs, and hasn't exactly burnished his "gamer" credentials in Seattle.

"Sometimes you get a guy and he's a little different than he looks from outside," former Mariners pitching coach Mel Stottlemyre told the Seattle Times. "Not to knock him, because he's a great talent, but basically he didn't have the leadership qualities I thought we were getting."

Josh Beckett
Beckett

The Josh Beckett trade (November 2005)

The deal: Florida sends Beckett, Mike Lowell and Guillermo Mota to Boston for minor leaguers Hanley Ramirez, Anibal Sanchez, Harvey Garcia and Jesus Delgado.

The backdrop: Lowell is coming off a down year and appears to be fading at age 31. Beckett, the hero of Florida's 2003 championship run, is about to get too expensive for the Marlins' tastes. The Rangers want Beckett badly, but a reported package of Hank Blalock and either John Danks or Thomas Diamond isn't enough to trump Boston's offer.

Ramirez has a world of talent, for sure, but he's gained a reputation for immaturity in the minors. The deal goes down while Boston GM Theo Epstein is on hiatus as a result of his spat with club president Larry Lucchino.

The initial reaction: One New York-based writer thinks the Red Sox pulled off a heist because Ramirez and Sanchez are "frauds" and beneficiaries of Boston-based hype.

The Boston press is generally upbeat about the trade because of Beckett's age and potential upside.

"Getting Beckett stands alone as a cause for celebration, because he is the type of pitcher who could have a Curt Schilling-like effect on the Sox' fortunes, for a Pedro Martinez-like period of time," writes Gordon Edes of the Boston Globe.

Florida's grade: A. Sure, Beckett has Mr. October-like qualities, and Lowell has been a great pickup for the Red Sox. But Ramirez is a perennial All-Star at a premium position, and he was signed to a long-term deal through 2014. With the exception of Sanchez's no-hitter in 2006, the Marlins' return from the other three players is minimal.

Mark Mulder
Mulder

The Mark Mulder trade (December 2004)

The deal: Oakland GM Billy Beane sends Mulder to St. Louis for Dan Haren, Daric Barton and Kiko Calero.

The backdrop: Two days after trading Tim Hudson to Atlanta, Beane says goodbye to a second member of the Big Three. The move apparently won't play well in the clubhouse.

"What the hell?" third baseman Eric Chavez tells the San Francisco Chronicle. "I don't understand. I don't know whether to be mad or shocked or what. I wasn't going to step in and say who we should keep, but I think this is getting borderline ridiculous."

The initial reaction: Oakland media outlets have faith in Beane's judgment, but wonder if the team isn't losing its identity with the constant retooling on the fly.

"At least Beane hasn't traded Stomper, the A's wildly irritating yet persistently obnoxious elephant mascot," writes San Jose Mercury News columnist Mark Purdy. "Yet."

Oakland's grade: A. Never mind that the A's turned around and traded Haren to Arizona three years later. Beane landed the better, younger pitcher in the deal. Calero gave manager Ken Macha two nice seasons in the 'pen, but those 70 appearances in 2006 took a toll. Barton is taking a while to develop, but he's only 23. Barton returned from the minors Monday and homered in a 14-13 victory over the Twins.

Dan Haren
Haren

The Dan Haren trade (December 2007)

The deal: Billy Beane trades Haren and Connor Robertson to Arizona for pitchers Dana Eveland and Greg Smith and minor leaguers Brett Anderson, Chris Carter, Aaron Cunningham and Carlos Gonzalez.

The backdrop: The A's have concerns about the health of third baseman Eric Chavez and pitcher Rich Harden. Beane, never one to trod the safe middle ground, decides to trade his most marketable commodity, Haren, and go young. The deal comes three days after Haren's wife, Jessica, gives birth to their first child, son Rhett.

The initial reaction: "Plenty of sadness in the A'sosphere that well-liked new daddy Dan Haren is gone after just three years -- and that the A's are apparently throwing in the towel on the 2008 season before it even starts. But there's no stathead consensus on how this deal will work out," writes the San Francisco Chronicle. Still, Beane is widely praised for acquiring five of Arizona's top 10 prospects.

Oakland's grade: B+. Anderson, 21, looks like the real deal. He has thrown 21 straight shutout innings in July. The A's sent Smith and Gonzalez to Colorado in the Matt Holliday trade, and Carter, Cunningham and Eveland are all in the minors. True, Haren has been incredible in Arizona, but the A's have no complaints over their haul.

Curt Schilling
Schilling

The Curt Schilling trade (July 2000)

The deal: Philadelphia GM Ed Wade sends Schilling to Arizona for Travis Lee, Vicente Padilla, Nelson Figueroa and Omar Daal.

The backdrop: Schilling is wearing out the Phillies' front office, and his time in the city has reached an end. He's clashed with Wade on more than one occasion and gone public with his desire to be traded. The Phillies are last in the National League East, and Wade's mission is to get as much young talent as he can in a single swoop.

The initial reaction: Philadelphia writers don't know what to expect from the four Arizona players, and they're conflicted over Schilling's departure. He makes life interesting, but sure likes to hear himself talk.

"He was not Robin Roberts or Steve Carlton. But love him or hate him, Schilling was one heck of a competitor who left a piece of himself on the mound every fifth day. The Phillies will certainly miss the horse," writes Jim Salisbury of the Philadelphia Inquirer.

Philadelphia's grade: C. It's easy to label this trade a bust, since Schilling achieved great things in Arizona and the Phillies failed to receive one high-impact player in return. Lee lived up to his reputation as a low-passion overachiever, and Padilla will be remembered in Philly as a hot-headed loner. But Padilla posted a 49-49 record in six seasons with Philadelphia, Lee hit 20 homers and drove in 90 runs in 2001, and Daal won 13 games that season. So it's not as if Wade received nothing in return.

Johan Santana
Santana

The Johan Santana trade (February 2008)

The deal: Minnesota GM Bill Smith trades Santana to the Mets for outfielder Carlos Gomez and pitchers Phil Humber, Kevin Mulvey and Deolis Guerra.

The backdrop: It's clear the Twins can't afford Santana once he files for free agency, so Smith has three options: (1) trade Santana now, (2) move him at the July deadline or (3) keep him, make a run at the AL Central title and then collect the draft picks.

Boston reportedly makes Jacoby Ellsbury, Jon Lester and Justin Masterson available in various packages, while the Yankees apparently are willing to deal pitcher Phil Hughes. The Twins wait so long that the market dries up, and the deal finally goes down on Groundhog Day. Shortly thereafter, Santana signs a $137.5 million extension with New York.

The initial reaction: "In poker terms, Smith slow-played a big hand and ended up dragging in less than the maximum pot," writes Aaron Gleeman on his Minnesota Twins blog.

Minnesota's grade: D. Yes, we know Smith's leverage decreased as the winter progressed, but in hindsight, the return sure looks light. If Gomez ever figures out the strike zone or Guerra amounts to anything, the deal still has some upside from Minnesota's end. But don't hold your breath.

Tim Hudson
Hudson

The Tim Hudson trade (December 2004)

The deal: Billy Beane sends Hudson to Atlanta for pitchers Juan Cruz and Dan Meyer and outfielder Charles Thomas.

The backdrop: After allowing Jason Giambi and Miguel Tejada to leave through free agency and pocketing the draft picks, Beane makes a pre-emptive strike and trades Hudson to Atlanta entering the pitcher's "walk" year. It's an interesting negotiation, with John Schuerholz and Beane matching up in a classic old-school, new-breed collaboration.

The initial reaction: The trade elicits a lot of emotion from Beane, who says the phone call to Hudson was the most difficult he's ever made to a player. Hudson posted a 92-39 record in Oakland and was revered by his teammates. Beane calls him "this generation's Dave Stewart."

Oakland's grade: D-. Meyer stagnated in Oakland because of arm problems before resurrecting his career in the Marlins' bullpen. Thomas fell off the map in 2007, and Cruz contributed 32 2/3 innings with the A's before being traded to Arizona for Brad Halsey. Oakland's return for Hudson is one step above the proverbial bag of balls.

CC Sabathia
Sabathia

The CC Sabathia trade (July 2008)

The deal: Cleveland sends Sabathia to Milwaukee for pitcher Zach Jackson and minor leaguers Matt LaPorta, Michael Brantley and Rob Bryson.

The backdrop: Sabathia gets off to a slow start in 2008, and the Indians come to grips with the realization that they're not going to sign him in free agency. So they shop him hard, and the Brewers spring into action. They assemble a strong package of young players to beat out six other clubs.

The initial reaction: It's wall-to-wall euphoria in Milwaukee, as fans buy more than 27,000 tickets the day after the trade is announced. "Sabathia mania hits Brewer nation," reads the headline in the Milwaukee Journal Sentinel.

Cleveland's grade: Incomplete. Questions linger about LaPorta's defense, but he is hitting .314 with a .927 OPS for Triple-A Columbus. The Indians plans to call him up and turn him loose once they can find at-bats for him. It might be at first base.

There's a lot to like about Brantley. He's a .388 OBP guy in the minors, with a terrific strikeout-to-walk ratio and 50-steal speed and instincts. The Indians foresee him as a Kenny Lofton-type producer, but he might have to slide over to left field with Grady Sizemore entrenched in center. "He's an athletic kid," said a National League front-office man. "He's going to be a good player."

Jerry Crasnick covers baseball for ESPN.com. His book "License To Deal" was published by Rodale. Click here to order a copy. Jerry can be reached via e-mail.

Jerry Crasnick | email

ESPN.com MLB Sr. Writer