Is Roy Halladay Too Old and Too Expensive?

Is Roy Halladay Too Old and Too Expensive?

So we are heating up, folks.

Last night we mentioned the burning desire in New England for the Red Sox to take some Thanksgiving-action and trade or sign for, a big-named player.

And not just anyone — but someone off of the “approved” fan list which reads as follows:

• Matt Holliday
• Jason Bay
• Adrian Gonzalez
• Felix Hernandez
• Jose Reyes
• Hanley Ramirez
• Miguel Cabrera
• Roy Halladay
• Prince Fielder

If the Red Sox were to sign the likes of John Lackey or Marco Scutaro, the response would be a collective “meh.” It would be a lot of “well, that’s cool, but we need to get (fill in the blank).” It looks like that ‘fill in blank’ might happen sooner than later.

Today, the hot stove is burning on high, with the recent push from the Toronto Blue Jays to deal ace pitcher, Roy Halladay. The Red Sox, Yankees and Dodgers all appear to be in the mix. Toronto would like to deal Halladay before baseball’s general managers meetings beginning Dec. 7.

Former Blue Jays general manager, JP Riccardi, was supposed to deal Halladay in 2009 at the instruction of the organization, but he never pulled the trigger. Some say that was the final straw ending his days in the Jays’ front office.

Now, Toronto wants to move Halladay as soon as possible in order to extract as much value as they can. Had Halladay been dealt last year, the Blue Jays could have demanded a ransom. Riccardi apparently wanted the world, not just a ransom, and today, Halladay remains a Blue Jay.

The Prospects

Toronto is rumored to be asking for two of the Red Sox best young players; Clay Buchholz and Casey Kelly. That is a top-line starter in Buchholz and the #1 rated prospect in the Boston farm system in Kelly. Is that too high of an asking price for a 33-year old pitcher?

A rotation that features Halladay, Jon Lester and Josh Beckett sounds like a dominant, World Series-winning pitching staff. Yet could it be a price tag that hamstrings the organization for years to come? The Red Sox traded Hanley Ramirez to the Florida Marlins for Josh Beckett and Mike Lowell. Those two acquisitions catapulted the Red Sox to their second World Series of the decade.

Today, Ramirez is the best shortstop in baseball. A rare blend of power, speed and average. The nice thing for the Red Sox front office is that Hanley is tucked away in the confines of the National League — buried in Miami, FL, where he cannot haunt them.

Would Kelly or Buchholz be different? Maybe. Toronto is a division rival that the Red Sox cannot ignore or avoid. To say that either player would reach the level of production and success that Ramirez has had is far fetched, but their immediate impact against the Red Sox must be factored.

Trading for Halladay would also require a contract extension. There is no way you hand over two top-flight prospects for a one-year rental. Halladay is heading into his 13th Major league season. He has a 3.48 career ERA and nearly 150 wins on his resume. So what kind of contract extension would you give him?

The Contract

In 2010, Halladay will make $15.75m. The Red Sox are going to want to presumably extend him an additional three years, which would probably total somewhere around 55-60 million dollars. Halladay would be 37 when the contract expired.

According to Fangraphs, Halladay’s actual on-the-field value has exceeded his salary every year since 2002. In 2009, he was paid $14.25m and was listed as worth $33m. If the Sox could tie him up at around $18m per year over the three years, Halladay will prove to be well worth it, especially if it nets the team another ring or two.

But could the Red Sox complete a deal with Toronto and not give up both blue chips? You would like to see them move either Buchholz or Kelly (with some lesser prospects) to get Halladay and then turn around and deal the other blue chip in a package to acquire a big-time bat.

Maybe we are playing a version of video-game general manager here, but both ‘Kelly and Buchholz to Toronto’ seems a little rich for a team desperate to move their ace. Halladay has already stated that he won’t re-sign in Toronto when his contract expires after 2010.

So what if it were Buchholz and Michael Bowden? Would that get it done?

The Biggest Risk

The real risk of course is the New York Yankees. A worst-case scenario would be for Boston to play hardball with Toronto and in-turn, the Blue Jays flip Halladay to the Bronx. It would be another season of Yankees fans reminding Red Sox fans about how cheap their organization is. They swooped in and gobbled up Alex Rodriguez and Mark Teixeira from Boston. New York acquiring Halladay would be a deadly blow.

The Yankees have been rumored to be considering offering Toronto a package that would include Joba Chamberlain, Phil Hughes and possibly a catching prospect. If New York pulls the wool over Boston’s eyes, it will be a long and irritating season as Red Sox fans waver between anger and hope.

Again, signing a John Lackey would be all well and good, but you don’t want to let the Yankees enter a playoff series with CC Sabathia, AJ Burnett and Halladay. With their already stacked-lineup, they could easily rattle off championships for the next three seasons. Lackey and his grossly exaggerated under bite would only serve as a reminder that the Red Sox refused to play big ball with the Empire.

One thing to always remember is that there are no guarantees with prospects. For every Hanley Ramirez there is a Jorge De la Rosa or a Brian Rose. Dealing both players is a hot button-topic amongst fans with possible long-term ramifications.

But a bird in hand is worth two in the bush.

Darryl Johnston is the Red Sox correspondent for Fanball.com. He has many years of sports writing under his championship belts. Email him – redsoxdj@gmail.com

Tags: Adrian Gonzalez, AJ Burnett, AL East, Alex Rodriguez, Boston Red Sox, Brian Rose, Casey Kelly, CC Sabathia, Clay Buchholz, Darryl Johnston, Fanball, Fangraphs, Felix Hernandez, Fenway Park, Florida Marlins, Hanley Ramirez, Jason Bay, Joba Chamberlain, John Lackey, Jon Lester, Jorge De la Rosa, Jose Reyes, Josh Beckett, JP Riccardi, Los Angeles Dodgers, Marco Scutaro, Mark Teixeira, Matt Holliday, Michael Bowden, Miguel Cabrera, Mike Lowell, New York Yankees, Phil Hughes, Prince Fielder, Roy Halladay, Sox Tea Party, Theo Epstein, Trade Rumors