The Roy Halladay Sweepstakes, Part One: The Major Players

Thomas HillContributor IJuly 16, 2009

ST LOUIS, MO - JULY 14:  American League All-Star Roy Halladay of the Toronto Blue Jays pitches during the 2009 MLB All-Star Game at Busch Stadium on July 14, 2009 in St Louis, Missouri.  (Photo by Morry Gash-Pool/Getty Images)

In the week since Toronto Blue Jays GM J.P. Ricciardi announced to the baseball world that the organization would be all ears to any trade discussions regarding ace Roy Halladay, over a dozen teams have checked in with the Canadian franchise.

Predictably, the asking price seems to be a package of three-plus young players/prospects, with the Jays preferring players that can contribute on the major league level within the next year.

It should also be noted that with Marco Scutaro having a breakout season in his free-agent year, the Jays would certainly look hard at any deal that includes a promising young shortstop.

With many teams still within striking distance of divisional or wild card contention, the AL’s best pitcher can count almost every team with a .500 record or better as a potential suitor.

While ESPN’s Buster Olney has already published his handicapping of possible Halladay destinations, let’s take a one-by-one look at the favorites, possibilities, and a few dark horse candidates vying for “Doc’s” services. Finally, I’ll finish up with a trade proposal that would suit both clubs.


Everyone predicts the defending champs will be the ones who land arguably the best pitcher in baseball, and it’s easy to see why.  Not only have they had a hole in their rotation since Brett Myers went down with a shoulder injury, but acquiring another front-line (i.e. Ace or No. 2) pitcher would instantly make them the NL favorite for the pennant.

Why? Ask any team if they would feel confident about their chances facing Cole Hamels and Halladay twice each in a playoff series. And, unlike a majority of the other contenders, the Phillies have a deep stable of attractive players that they can trade without hindering the future or depleting the farm system.

Icing on the cake from the Jays perspective is that many of Philadelphia’s better prospects are pitchers and another is a shortstop, Jason Donald, who could be the key to this trade. Known more for his defense and rocket arm when drafted in the third round, Donald’s bat has developed to the tune of being a .297 career hitter in the minors entering 2009.

In fact, after scorching major league pitching this past spring training, Donald was penciled into the Phillies lineup at either or second or third base if Chase Utley or Pedro Feliz were injured to start the season. Of course, that was before he was hitting .230 through 50 AAA games after he suffered a torn meniscus in his knee.

However, Donald has just resumed playing games and should still be considered a possible trade chip that Toronto would be interested in. Pitching wise, the Phillies have a crop of youngsters highlighted by JA Happ, Kyle Drabek, Antonio Bastardo and Carlos Carrasco.

All except Drabek have pitched at the Major League level at some point this year and Drabek is knocking on the door with his pitching in the AA Eastern League for Reading. The Phils also have highly regarded positional players in outfielders Dom Brown and Mike Taylor, and catcher Lou Marson.

Taylor, a Stanford product, is closer to the big leagues, but Brown has the higher ceiling.

Trade Proposal

Halladay for Donald, the Jays’ choice between Brown and Taylor, and the Jays’ choice of one from the group of Carrasco, Bastardo, Happ, and Drabek. My guess is the Phillies initially offer Taylor, Donald and Bastardo but are willing to substitute in Brown, Happ, Carrasco, etc.

I think they will try to hold onto Drabek unless Ricciardi is insistent on acquiring him. Ultimately, something like Brown/Donald/Carrasco could be the final product.

This trade gives the Phillies the upper hand in the National League while giving the Jays a Major League ready starter in Carrasco, a high upside outfielder a couple years away in Brown and a cheap option to try out at shortstop in Donald in the event Scutaro bolts for the greener pastures of free agency.


The Los Angeles Angels of Anaheim have been dealing with pitching injuries and ineffectiveness all year, coupled with bouts of inconsistency. Despite these hindrances, they remain in first place in the AL West.

Adding Roy Halladay to a rotation that already includes John Lackey, Jered Weaver, and Joe Saunders would wreak havoc on many a team, and would match up well against the other high-octane rotations of the AL, such as the Red Sox and Yankees.

The Angels are also brimming with top flight prospects, especially at the two positions most important to the Blue Jays: Shortstop and Pitching.

Brandon Wood, with his prodigious power, has seemingly been one of the Angels top prospects for half the decade but has been blocked by Erick Aybar, another top young player in his own right.

To acquire Halladay, the Angels would probably let the Blue Jays choose between the two. As far as pitching is concerned, flamethrower Jordan Walden has held his own at just 21 years old at AA Arkansas and lefty rotation-mate Trevor Reckling, even younger at 20, played in this year’s Futures Game in St. Louis.

Other prospects of note include outfielder Peter Bourjos, catcher Hank Conger, and first baseman Mark Trumbo. The Angels would probably also dangle ineffective starter Ervin Santana, and he would offer serious upside to the Jays if he returns to form.

Trade Proposal

Halladay for a choice between Wood and Aybar, along with Reckling, Santana, and another young arm such as Kevin Jepsen or Anthony Ortega could be a feasible swap. The Angels get the ace for a talented collection of young players, but all of which are expendable.

They have a glut of young shortstops and several other high-impact arms awaiting their big league opportunity. The Jays get a rotation replacement in Santana who could very easily return to his pre-2009 form, a young shortstop to replace Scutaro, a top-tier pitching prospect already at AA, and a bullpen arm.


Some people don’t see San Francisco as a major player in the Halladay auction, but I think they should be for the sole reason that a rotation made up of Halladay, Tim Lincecum, Matt Cain, Jonathan Sanchez and Barry Zito/Randy Johnson would absolutely, unequivocally level the playing field between the Giants and the current best team in baseball, Los Angeles Dodgers.

Madison Bumgarner, at a mere 20 years old, is carving up AA hitters and was slated to start the Futures Game this past week. He is one of the top three pitching prospects in the game (with Stephen Strasburg and Aroldis Chapman being the other two, in my opinion).

However, he is probably untouchable, and I would venture to say that last year’s first round pick, catcher Buster Posey, is as well.

The Giants do have some other pieces to offer though. Corner infielder Angel Villalona, “The Big V”, is considered an elite level bat, albeit he is still in the lower minors, far from impacting a major league team.

Pitcher Tim Alderson, another 20 year old in AA, would certainly entice the Jays, and the Giants would almost certainly have to include him in any deal for Halladay that doesn’t include Bumgarner or Posey.

Trade Proposal

If I’m the Giants, I offer Alderson and Villalona and hope that is enough to strike a deal. It could be effectively argued that those two offer the most combined upside of any two prospects the Jays could get for Halladay.

Adding someone like shortstop Brian Bocock could be enough of a sweetener to facilitate a trade. The Giants would immediately transform the NL West into an all-out battle with the Dodgers.

In return, the Jays get a great pitching prospect in Alderson who could make an impact next season, a high potential player for later in Villalona, and a shortstop in Bocock that could compete for time when Scutaro leaves.

Yankees/Red Sox

I am grouping these two together, because while they are always major bidders when a talented player is on the trading block, they also share the AL East with Toronto, thus making them unlikely trade partners.

How can the Blue Jays sell their fans on trying to compete if they trade their single best player to a divisional rival that they face multiple times every season.

It is not out of the realm of possibility, however, that one of these two empires will construct a three-way deal behind the scenes without the Blue Jays’ knowledge to acquire Halladay. Either way, Yankees and Red Sox would both have to pony up the same bounty of prospects, just necessarily emphasizing a close-to-ready shortstop.

For New York, pitchers Phil Hughes, Joba Chamberlain, and AA All-Star Starter Zach McAllister, as well as their top prospect, catcher Jesus Montero, would be atop any team’s wish list.

Major leaguers Melky Cabrera and Brett Gardner, with their improved play in 2009, would merit consideration for a team looking for an outfielder to get on the field right away.

The Yankees, who have completely overhauled their farm system over the course of the last five years, also have intriguing talents such as 6’8" pitcher Dellin Betances, last year’s top prospect in AAA outfielder Austin Jackson, and catcher Austin Romine.

Ramiro Pena, Francisco Cervelli, Phil Coke, Alfredo Aceves, and Mark Melancon are other young players that have seen action in the Bronx this year. To make it worthwhile for either Toronto to deal directly with them or convince another team to execute some kind of controversial three-way deal to land Halladay in New York, the Yankees will have to offer an overwhelming package.

To me, that would mean one of Joba, Hughes, or Montero plus at a combination of least two, and probably three, top prospects and/or MLB-ready young players. Perhaps something like Chamberlain, Cabrera, Cervelli, and Betances could work. That’s a high price to pay, but imagine facing CC, Doc, and Burnett three days in a row.

For Boston, a trade for Halladay would mean pairing Doc with Josh Beckett, Jon Lester, All-Star Tim Wakefield, and whomever they feel like putting at No. 5 for an incredible rotation.

Lars Anderson, their top prospect, would be the first player another team would covet, and the BoSox certainly have MLB-ready pitching prospects in Clay Buchholz, Michael Bowden, and Daniel Bard.

Outfielder Josh Reddick has five-tool potential, and A-level prospects Casey Kelly (P/SS), Yamaico Navarro (SS), and Stolmy Pimentel (P) all highlight the list of Boston’s top prospects.

Other notable prospects include SS Ryan Dent, OF Ryan Kalish, 3B Michael Almanzar, and 1B Aaron Bates. Established big leaguers such as Justin Masterson and Jacoby Ellsbury could even be discussed in a deal to net Halladay.

If I’m the trade partner, I emphasize that the rival Yankees are in discussions and refuse to settle for a trade package of anything less than Anderson, one of either Bard, Masterson, or Buchholz, and two other prospects, preferably Reddick and one of the A-level pitchers.

Coming up next: Part Two, Second Tier Trading Partners