“The Red Sox playoff rotation has been finalized. Starting Game 1 at home against Detroit will be Josh Beckett with Roy Halladay to follow in Game 2. Jon Lester gets the nod in Game 3 in the Motor City.”
It’s entirely possible we could be hearing roughly those three sentences when the leaves change, the temperature drops, and the thoughts of another World Series title is floating around the collective heads of Red Sox fans across the globe. It’s entirely possible that by gutting the top of our loaded farm system, Massachusetts native J.P. Ricciardi could deal Toronto ace Roy Halladay to the Olde Towne team, giving Boston the strongest 1-2-3 punch in a playoff rotation in recent memory.
Am I naïve to think this could actually happen? Is this simply a pipe dream with no hopes of actually coming to fruition? I tried to calm myself down Tuesday afternoon when the news broke by Ken Rosenthal that Ricciardi will listen to offers for Halladay because there’s no way he trades his ace to a team in the same division, especially given the large number of games the Jays and Red Sox face off in the second half. Then Rob Bradford at WEEI.com reported that J.P. was not averse to trading Halladay within the division if it meant the best package was offered by Boston, New York or Tampa, which makes sense.
Is it a given that Halladay is dealt before July 31? Of course not. Ricciardi may not find a package that flutters his interest, and, worse case scenario, he has his horse for the 2010 season, the final year of his expensive contract. What could aid the process of dealing Doc is a guarantee by the Jays owner that J.P’s job is safe during a total rebuilding process. That way, he’d feel a lot more comfortable dealing Doc for a pile of high-ceiling prospects in hopes of Toronto contending 3-4 years down the road.
Who are the best fits in a potential Halladay trade? Due to his contract- around $7 million owed the second half of this season and almost $16 million due for 2010- it would likely have to be a big market club. This is NOT similar to a small-market Milwaukee team picking up C.C. Sabathia in early July last year because C.C. was a free agent at the end of the season. The $16 million could be a deal-breaker for teams like the Rangers, Brewers and Rays, who would love pitching but cannot afford the contract.
The White Sox had a deal with Jake Peavy done until he nixed it. We know how active Ken Williams is around this time, but would they be willing to surrender Gordon Beckham (rumor is that Toronto would love to add a shortstop and he’d be a perfect fit)? He could be the difference in a bad division. The Mets would have to gut their already mediocre farm system, surrendering Fernando Martinez. The Angels and Cubs lack the impact prospects the Jays would be looking for. The Dodgers would be a great fit, but would they be willing to part with Clayton Kershaw? It’s doubtful.
That leaves three potential suitors that I believe are the best fits: Phillies, Yankees and Red Sox.
The Phillies should win the NL East even without adding pitching, but can they really enter the postseason with Cole Hamels not completely right, Brett Myers injured, Jamie Moyer ineffective and J.A. Happ in the playoff rotation? They’d love to add Roy Halladay and may have the high minors pieces to add him with shortstop Jason Donald (although he’s hurt and was struggling this year), pitcher Carlos Carrasco and catcher Lou Marson. The Phillies also play in the NL meaning Ricciardi doesn’t have to worry about Halladay beating his team repeatedly the next year and a half. Would that be an attractive enough package for the best pitcher in the game? They’d be able to contribute right away, but there’s much debate on those three prospects and their respective ceilings.
Could the Yankees snatch Halladay and instantly promote their team as World Series favorites with a Halladay-Sabathia-Burnett trio at the top? Much like the Santana negotiations two winters ago, Phil Hughes may be the deal-breaker. Ricciardi will surely ask for Hughes in any deal and the Yankees would be reluctant to deal him at this point, especially considering Chien-Ming Wang’s return to the DL and the fashion in which Hughes has stabilized the eighth inning for Joe Girardi. He may also be needed in the rotation. A Hughes/Montero/Jackson package should get the job done.
The Phils and Yanks will likely get involved. But the best fit for Roy Halladay is the Boston Red Sox for an assortment of reasons.
1. The Red Sox can easily take on his contract. Boston’s payroll decreased for the third straight year and is now $22 million lower than the 2007 total. Missing out on Mark Teixeira at $170 million and instead opting for cheaper free agents like Smoltz, Baldelli, Penny and Saito was disappointing, but it gives Theo tons of payroll flexibility both at the deadline this year and next offseason. I understand that the economy will still make the Red Sox front office cautious, but they should be able to easily take on Doc’s $23 million or so and also be able to entertain extension talks. Beckett and Halladay are both off the books after the 2010 campaign.
2. The Red Sox have the best prospects to offer. As Curt Schilling said yesterday on WEEI, this is why you build a farm system as a big market club. Not only are you able to fill holes with cheaper options, but when a golden opportunity like Roy Halladay being available comes along, you have the upper hand. Casey Kelly is likely untouchable, but would a Buchholz/Anderson/Delcarmen package get the job done? What about Buchholz/Anderson/Bowden? What about Anderson/Bowden/Bard/Reddick? There are plenty of options here, and if you cringed at dealing that type of incredible package, REMEMBER THAT ROY HALLADAY IS THE RETURN, possibly the most sure-thing when it comes to pitching in baseball.
3. J.P. Ricciardi grew up a huge Red Sox fan. Remember the Kevin Garnett deal? Don’t think this doesn’t matter. At least this is what I keep telling myself.
4. They don’t have to outspend the Yankees, they just have to out-prospect the Yankees. Rather than let all of these gems reach free agency where the Pinstripers will pounce, blockbuster trades every 3-4 years may be the route the Red Sox need to go. It’s not like the Red Sox are the Pirates or Indians, but the Yankees still have a payroll around $80 million higher than Boston’s. Josh Beckett in 2006, Roy Halladay in 2009?
While some may conclude I need to remove the Red Sox-colored glasses, when one actually breaks this down, and if J.P. Ricciardi is willing to deal within the division, Boston appears to be the best fit. Roy Halladay would jump at the chance to pitch in October for the first time in his career, waive the no-trade clause, the Jays end up with a boatload of talented young players to build around and the Red Sox have the best rotation in the game.
If Halladay is being fitted for a Red Sox uniform around July 31, you can start making room for the banner.

I agree. I think a perfect deal would be:
Bowden, Lowrie, Anderson, Bard.
I don’t think you have Red Sox colored glasses, Zach. Unless the Yankees are willing to part with Joba or Montero+Hughes, Boston is the best fit. That said, I don’t think Evan’s deal gets done, if only because there is no elite talent in that deal. Anderson is a very good prospect, as is Bowden,but I highly doubt you get a deal done without Buchholz. I think Toronto is going to want a team’s top prospect, or a former top prospect now showing something in the majors. I think both of the deals including Buchholz that you mentioned would probably get it done, although they would push for Lowrie as well. Basically, I would guess the Sox would offer, if serious, Buchholz, Anderson, and Delcarmen, and Toronto would want Lowrie rather than Manny. Should be interesting.
Okay, then Buchholz. But Anderson not elite? Come on.
Anderson is not an elite prospect in my book- he is a top 30 guy, but likely not a top 15 guy after struggling in AA. I guess it depends on how you define elite.
This will be fun to follow, no doubt. Seems the Sox and Yankees have the most to offer, if either team gets Halladay pencil them in for a WS appearance
Buchholz would need to be in the deal. Anything short of Buchholz, Anderson, Bard, and another player (Reddick/Lowrie/Bowden) won’t likely get it done.
The Jays can always deal him next year at the deadline and have more suitors. Could pay to wait.
Tim, you think it would necessarily require Buchholz, ANderson, AND Bowden/Lowrie? That is quite a haul. If I was Boston, I think one elite prospect and one upper level prospect should be plenty, and then supplement with bullpen types or single A high risk high reward types.
I can still see the Phillies overpaying for Halladay since they seem to be so overwhelmingly desperate for starting pitching, and Halladay would obviously much improve their chances at repeating.
As for the Sox, even if Ricciardi loves us it’ll still cost a ton of good players to acquire him, and I don’t know if Theo would actually pull the trigger.
Any package would start with Buchholz and Lars, and from there you’d have to add. Lowrie might have to be in it since it’s said they really want a SS, but maybe we can sell them on a guy like Diaz in AA as a great glove/low bat guy, plus a guy in High A like Mailman.
Doing any deal for Halladay would make trading for an impact bat nearly impossible, and the Sox need the bat much more. Maybe Halladay packaged with Scott Rolen could work, and taking the extra salary could lower the demands, though probably not much.
No no no no no no no. Why would we trade our top pitching prospects for another pitcher? We have enough young(ish) arms to keep us afloat for years, and absolutely nothing in terms of sure-thing power. Maybe if Anderson had a .900 OPS right now in AA or if that .764 was in AAA, but I am not remotely confident that we have a bat for the future that isn’t currently in our MLB infield.
He may be an ace, but he’s 32 and has more miles on his arm than pretty much any pitcher in the league with all those CGs. Were he 28 I’d say go for it, but there is no reason to trade for pitching right now.
I agree with Sean. Hell, even if this was two years ago I’d make the deal. But as I said on The Bottom Line, Halladay only has one year left on his current deal and he’d sign an extension for only a stupid amount of money. I don’t want to sign a 33 year old pitcher to a five year (at least) 100 million dollar contract
I think Moshe is on target with the parameters of a trade. Buster Olney says the Jays would want three top prospects. Remember, unlike Sabathia in 2008, Halladay isn’t a short-term rental; he’d be under team control for a year and a half. So he’s a more valuable commodity than Sabathia was.
To me, a blockbuster deal only makes sense if you’re willing to give Halladay a contract extension. (Since he has a no-trade clause, he might even insist on an extension as a condition of approving a deal.) If you do that, you’ve removed a lot of your up-and-coming (cheap) talent and taken on another top-level contract — probably four more years at 20MM/year. That would severely limit the Sox’ ability to (a) sign the young players who become eleigible for arbitration or free agency, and (b) sign or trade for other high-priced talent, such as a new cleanup hitter or catcher.
Personally, I’d love to see Halladay in a Sox uni, but you do have to consider all the ramifications of such a deal.
One other consideration: I’m sure the Jays would prefer to trade Halladay outside the division. They’ll look to the NL first. Olney mentioned the Phillies as a team with a high budget, good prospects, and a real need for starting pitching.
Everyone is completely overblowing Anderson’s struggles, he’s only 21, and if you take out a terrible May his stats aren’t so bad, honestly I’d rather part with Buchholz. I’d offer Buchholz/ Bowden/ Reddick and maybe throw in Hagadone if it gets it done. Fact of the matter is there are only 2 pitchers who we can comfortably rely on come October, Beckett and Lester, Halladay makes this the best team in baseball no doubt.
Bad idea. Trading for Halladay would be a huge mistake IMHO. Halladay is an Ace, but we don’t need pitching; in fact, pitching is our main point of strength right now. We need OFFENSE, and if we go after Halladay, not only we are gonna lose any oportunity to get the bat we need, but we are gonna lose the best bat we have in the farms (Anderson) in the process. This means we are gonna DOWNGRADE the offense to add even more pitching surplus. It makes no sense to me.
If we are gonna go for the blockbuster, it has to be for someone like Adrian Gonzalez or V-Mart, who can be a big upgrade right now and for the future. Not for a 32 year old pitcher, who we don’t need.
what pitching surplus? I’d buy this if Dice-K had been anywhere close to effective this year, but the pitching staff is essentially Beckett, Lester and a bunch of guys who are hit or miss
Just want to remind everyone that Roy Halladay is the best pitcher in the American League.
Throwing that out there.
Great thread. IMO, the problem in 2008 was pitching, both SP and RP. Theo solved both problems before ST. 2009 pitching is outstanding, but at this point our surplus is a bit of a chimera with
Daisuke on the DL, and Smoltz/ Penny/ Saito/ Ramirez/ MDC/ Papelbon/ Bard all struggling with consistency. Depth, now and in 5 years, comes from potential stars Buchholz & Bowden, Tazawa & Hagadone.
Yet, I agree with MAG
V-Mart is signed through the end of next year, the same as Halladay, so the two will help you for now and next year, not the future, barring an extension. A Gon will obviously help you for now and the next two years, as his deal is only for a year longer than the other two, although he might be open to a pre-FA extension.
And I honestly don’t think Halladay is coming here. It just doesn’t make sense in many ways. Theo won’t give up top prospects to a divisional rival, even for a guy like Halladay.
Lowrie is not valuable to anyone except the Red Sox right now. Given Green’s offensive slowdown and Lugo’s defensive dysfunction the Sox need Lowrie. If Bowden, Delcarmen and Andersen get the deal done – great. If it has to be Buchholz instead of Bowden, bite the bullet and do it.
If Rolen is part of the deal with Halladay – Buchholz, Bard, Reddick and Anderson would be great for both teams.
I want no part of Rolen, replacing one injury prone, aging, 3b with another isn’t exactly prudent.
I don’t want to give up Anderson, espec. within the division, but if you can get it done with ot without him, getting Halladay is a smart move, it clears the path to another ring, which after all is the goal. There’s plenty of pitching in AA and below for the future, and developing prospects is very important, but let’s not confuse the means and the ends. Getting Halladay makes this easily the best team in the AL for the next 1 1/2 seasons, the Sox missed a chance to do that with Santana (could have done that deal w/o Lester, look at what the Twins got and tell me otherwise) they shouldn’t miss that chance again
It is fun to think about, but I think we all know this kind of deal is against the Sox organizational philosophy. Trading loads of young talent is not happening, unless it brings back a cornerstone piece, like the Beckett deal. Of course, Halladay could be the cornerstone of any club, but in the Sox’ case he might not be worth Buchholz alone. They like to keep things profitable, and 6 years of Clay, who could be an ace himself is a bargain I don’t see them trading for anything.
I agree with Ted.
Joesox, when I say I want someone who can be an upgrade for right now and for the future, I’m asuming an extension. If we are gonna trade the farm, I want to do it for a player who can be signed for a contract extension. I don’t have any problem with giving extensions to V-Mart or Adrian Gonzalez. V-Mart has 30 years old and Adrian Gonzalez only 27, they are elite hitters who are gonna be productive for many years to come.
But I cannot say the same thing about Halladay. Is he the best pitcher in the American league? Probably. But for how long? I know the guy is amazing, but he is still a 32 year old PITCHER. And I’m not comfortable with giving a long-term extension to a 32 year old pitcher, even if it is for a guy as good as Halladay.
And I still think Dice-K is gonna rebound. He is having some problem right now, but he is better than this. Even if you don’t consider him an Ace, I still think he can be a more than reliable 3rd starter. And I think Kelly, Bowden, Tazawa, Hagadone and others give us good reasons to be optimistic about the future of our pitching. Maybe not every one of this kids are gonna be an Ace, but we have a lot of potential here.
And, by the way, this is the reason I wanted to sign Sabathia in the offseason. We could have signed him for only money, without losin anyone. But the FO didn’t even try.
so if V-Mart is in the picture, what’s he worth to the six? And as everyone is wrapped up in the Halladay conversation about cost in prospects and salary (not to mention age), how about Cliff Lee? He is 30, signed for the same years for a lot less money.
So, instead of Halladay, for a larger but similar trade package and less $$, we get Lee and V-Mart. V-Mart solves the bat problem, and provides rest for Papi, Tek, Youk and, indirectly, Mike; and replaces Lars. And Lee replaces Buchholz. Beckett, Lester, Lee is nearly as formidable as Beckett, Lester, Halladay; and V-Mart improves the lineup. Have to keep Lowrie, though, as SS and to back Mike.
I like Lars Anderson a lot. However, after watching him play at Hadlock it appears that he is a California kid who can’t play in the cold weather. The Sox love to play in October so he may not be the best fit for Boston. San Diego bound? I would love to have Adrian Gonzalez playing for the Sox.
I don’t think you get both Lee & Victor for a “similar” package as Halladay. I would guess one of them brings a similar but slightly less costly package of talent, as both are very good at what they do and are signed for the same contract length as Halladay, but for much less money.