The Roy Halladay Sweepstakes: Part 2, The NL Central

Thomas HillContributor IJuly 18, 2009

NEW YORK - JULY 04:  Roy Halladay #32 of the Toronto Blue Jays pitches against the New York Yankees on July 4, 2009 at Yankee Stadium in the Bronx borough of New York City.  (Photo by Nick Laham/Getty Images)

In the first installment of my in-depth analysis of possible trade scenarios that would relocate All-Star Game starter and Toronto Blue Jay Roy Halladay, I looked at the perceived favorites in the bidding war for the “Doc”.

Part 2 discusses teams that for various reasons, fall just a notch below the likely destinations for the arguably the game’s best pitcher.

Interestingly, a majority of these teams fall into the Central Division of the National League.


Milwaukee Brewers

We know that Brewers GM Doug Melvin is not afraid to pull the trigger on blockbuster mid-season deal, as evidenced by last season’s trade for CC Sabathia. Would he do it again for Halladay?

Well, first of all, the situation is very different. Halladay would not merely be a 2-3 month rental, but would also be in the fold for next season.

Second, the NL Central is an absolute wild-card division that has five teams that could conceivably make the playoffs this year (Sorry, Pittsburgh). They have a similar, offensive-minded, close-to-MLB ready player in Mat Gamel to the player they traded for Sabathia, Matt LaPorta (Who, in case you were wondering, hit .190 with Cleveland this year before a demotion back to AAA where he has since hit to the tune of .309 with 11 home runs).

The Blue Jays, however, are probably much more interested in Alcides Escobar, who has hit .296 at AAA this year after previously being touted as a strong-armed fielding whiz whose bat lagged behind.

Escobar’s potential as a shortstop is second to none when compared to other shortstop prospects the Blue Jays could acquire in a deal for their ace.

However, Milwaukee could instead substitute current starter JJ Hardy into a deal and hope Escobar turns out to be better.

Catcher Angel Salome, pitcher Jeremy Jeffress and Second Basemen/Catcher Brett Lawrie are other highly ranked prospects that Toronto could be interested in. 


Trade Proposal

Mat Gamel, JJ Hardy, and another lesser prospect for Halladay. Toronto gets a shortstop for the future and can spin Scutaro in a separate deal to a contender.

Gamel, who is probably best suited to play outfield on the major league level, is the key piece in this trade, and how he develops will determine who got the better end of this deal.

For the Brew Crew, they get to pair Halladay with Yovani Gallardo for a potent 1-2 punch that can wreak havoc on NL lineups.


St. Louis Cardinals

Imagine a rotation of Adam Wainwright, Roy Halladay, Joel Pineiro, Kyle Lohse, and Chris Carpenter. One through five, those hurlers match up well against any team on any given day.

I’m convinced the Cardinals win the National League pennant with this pitching rotation. Even against the current NL-best LA Dodgers, the Cards would have to be considered the favorites.

Randy Wolf and Hiroki Kuroda versus whoever you decide are St. Louis’ four and five pitchers? I’ll take the Cardinals every time.

Who would they trade in a deal? Well, Colby Rasmus is as close to untouchable as possible but maybe last year’s first rounder, Brett Wallace, is not.

Wallace is a premier bat who has risen all the way to AAA in his first full season of professional ball, where he’s hitting .296.

With Lyle Overbay and Scott Rolen entrenched on the corners in Toronto, I’m not sure where he will play but they find spots for kids that hit this well.

St. Louis can include MLB-ready pitchers Jason Motte and Clayton Mortensen to satisfy Toronto’s pitching needs and one more decent prospect such as outfielder Daryl Jones or shortstop Peter Kozma should be enough.


Trade Proposal

A trade of Halladay for Brett Wallace, Jason Motte, Clayton Mortensen, and Daryl Jones could work. Surely, this is an absolute ransom for the Cardinals to give up, as those prospects are the crown jewels of the St. Louis farm system.

However, for a chance to become the dominating team in the NL Central and even all the NL, it’s a price worth paying. Toronto stocks up on advanced level prospects that can each contribute within a year.


Chicago Cubs

They were heavily in pursuit of another pitching ace, the Padres’ Jake Peavy, earlier this year. With Zambrano being a loose cannon this season, Halladay would stabilize what has been an erratic pitching rotation highlighted by Ted Lilly.

The Cubs would not be opposed to trading power reliever Carlos Marmol, who failed to hold down the closer’s role early this season. Additionally, including one of their two third-base prospects, Jake Fox or Josh Vitters, would entice the Jays.

Toss in reliever Kevin Hart and a low-minors prospect with intrigue such as pitcher Dae-Eun Rhee, and you have the framework of a deal.

The only way the Cubs stand a chance in the NL Central against Milwaukee and St. Louis is to make a major splash at the trade deadline.

That would mean Halladay, and the worst thing that could happen to Chicago is seeing him arrive to the NL Central in a Brewers or Cardinals uniform.


Trade Proposal

Because they are bidding against divisional rivals for the services of Halladay, the Cubs most likely try to raise the price, including top prospect Vitters, Marmol, Hart, perhaps lefty Sean Marshall, and another prospect or two.

This move could decimate the Cubs bullpen but shore up a questionable rotation.

Toronto would probably rather have the packages mentioned above from Milwaukee or St. Louis, but Vitters and Marmol offer extreme upside, plus the other parts provide a lot of secondary value.


Houston Astros

An extreme dark-horse candidate, the ‘Stros are on the fringe of truly being competitive for the post-season at this point. Halladay to Houston would make for a very interesting NL Central race, immediately legitimizing the Houston team.

Teaming Halladay with another Roy, Astros incumbent ace Roy Oswalt, and the improved Wandy Rodriguez would certainly make a formidable staff.

The Astros have had one of the weaker farm systems in recent years, and have even had their draft prowess questioned after seemingly reaching for players and over-drafting for need rather than sticking to the conventional strategy of “best-player available.”

However, those same questionable draft choices, namely catcher Jason Castro and pitcher Jordan Lyles, have proved a lot of people wrong and made the Houston draft team look very smart with their development over the past year.

They also could dangle emerging outfielder Michael Bourn or other pitching prospects such as Ross Seaton and Bud Norris. I think Houston might make a call to Toronto to gauge Halladay’s price, only to find that it will cost selling the farm for a team that has only just rejuvenated its system with some talent.


Trade Proposal

Unlikely to be consummated, a deal of Castro, and two of three out of Lyles, Norris, and Seaton could be enough, but I think Houston wouldn’t even let that deal get on the table.

Those are some nice prospect pieces, but ultimately Toronto can probably get a better deal elsewhere, even from among teams in the NL Central alone. It would be shocking to see Halladay wearing an Astros uniform.


Cincinnati Reds

Another long-shot candidate who probably checks in with Toronto just to see the asking price, the Reds (like the Astros) entered the second half of the season only 3.5 games out of the NL Central race and 4.5 games out of the wild-card.

The Reds could use a shot in the arm for their pitching rotation as much as any team in baseball. Cincinnati is currently running out a rotation of Aaron Harang, Bronson Arroyo, Homer Bailey, Johnny Cueto, and Micah Owings.

Harang is a tier below the best pitchers in the game and is more of a good number two pitcher than an ace. Cueto has his dominating games but also gets shelled a fair amount, while Bailey has never been able to translate his electric stuff and minor league success to the major league level.

Arroyo and Owings don’t scare anyone. Halladay would instantly be the Reds’ best pitcher and enable them to match up more comparably against other NL Central stalwarts like Adam Wainwright, Ted Lilly, Yovani Gallardo, and Roy Oswalt.

The Reds also have the means to acquire Halladay, with many talented young players. To start, Bailey or Cueto would be included to fill the rotation hole in Toronto by trading their ace. Both have spectacular stuff, particularly electric fastballs, but have been unable to develop any sort of consistency.

First baseman Joey Votto can hit a ton, but has been dealing with anxiety and stress-related emotional issues that caused him to miss time this season.

The Reds bullpen has some power arms that may be of interest to Toronto, including Josh Roenicke, who has struck out over 8 batters per 9 innings this year.

For minor leaguers, former Little League World Series hero Todd Frazier has shifted from shortstop to third base to outfield throughout his minor league seasoning, but continues to hit (.314 at AA this season).

Former first round picks Drew Stubbs (.277 with 33 SB at AAA while playing outstanding defense in center field) and Yonder Alonso (.287 with 45 RBI between A and AA ball) could be dangled, as could Chris Heisey, who has come out of nowhere from Division III Messiah (Pa.) to not only make the Futures Game in St. Louis this year, but hit .349 with 16 HR, 54 RBI, 16 SB, and an almost 1:1 strikeout to walk ratio between AA and AAA this season.


Trade Proposal

Halladay for Bailey, Heisey, Roenicke, and an additional prospect, such as low-A pitcher Kyle Lotzkar (11.85 K/9) or even Frazier would be an interesting swap.

Halladay steps into the ace role while sliding Aaron Harang to his more suitable position as No. 2 while Toronto gets a rapidly improving (and potential 5-tool player) in CF Heisey, a one-time Top 10 pitching prospect in Homer Bailey (who is still only 23), a power arm for the bullpen in Roenicke, and another prospect to develop.


Up Next: The Third and Final Part of the Halladay Sweepstakes, The Extreme Long-shots


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