The period betwen the All-Star break and July 31 is always full of rumors and speculation.  One of the best places to follow all of the rumors is at MLB Trade Rumors.  Tim Dierkes, the proprietor of MLBTR does a terrific job of following all of the scuttlebutt.  While Tim covers the entire league, my main concern is just with the Cubs.  So today, I want to consider the question, what do the Cubs have to do to land Toronto Blue Jays pitcher Roy Halladay?

The easy answer is that they need a new owner in place before July 31 who is willing to take on payroll.  That answer’s not much fun since it is highly unlikely that the Cubs new owner will be in place before the trade deadline.  So for the moment, let’s assume that Jim Hendry will be given permission to add Halladay to the roster if he can make a deal.  Otherwise, this will be a very short post.

According to reports, the Phillies, Yankees, and Dodgers are the three most likely landing spots for Halladay if he is traded.  In my opinion, the Yankees are an extreme longshot since they play in the same division as Toronto.  I can’t imagine the J.P. Ricciardi would be willing to trade his ace inside the division. 

Another way to look at this is that the entire purpose of trading Halladay is to acquire prospects that can help the team win in the future (as well as budget relief).  So why would Toronto trade Halladay, arguably the best pitcher in baseball, to one of the teams they will be competing against in the division?  To me, it just doesn’t make sense.

However, Anthony Reber of Newsday.com has an idea that could potentially make sense to Toronto.  What if the Yankees were willing to take on the contracts of Halladay and CF Vernon Wells in exchange for 3-4 prospects?  Wells is owed $110 million over the next 4 1/2 years, a contract that Toronto would certainly like to jettison.  If the Blue Jays could rid themselves of two very big contracts, they would be able to redirect their payroll in ways that could make the team more competitive more quickly.

It’s an interesting argument.  With so much payroll flexibility and 3-4 of the Yankees top prospects, the Blue Jays could build a potential contender.  However, my argument holds.  I just don’t see Toronto trading Halladay in the AL East.

What about the Dodgers?  Any trade for Halladay would likely include Clayton Kershaw going to Toronto and Ned Colletti of the Dodgers has basically made him untouchable.  The Dodgers love their prospects and with one glaring exception, they normally shy away from commiting too much of the payroll to one player.  Halladay will cost them (or anyone else that trades for him) about $7 million for the rest of this season and $15.75 million in 2010.  With the exception of Manny Ramirez, the Dodgers don’t have anyone on their roster commanding that share of the payroll budget.  I consider the Dodgers to be a longshot to land Halladay.

That leaves Philadephia.  They just signed Pedro Martinez for the remainder of this year, but they insist his signing will not prevent them from pursuing other players.

Philadelphia has a definite interest and need for Halladay.  They also have the prospects that would be needed to make the trade; or at least they did until yesterday.  According to Ken Rosenthal at Fox Sports, Jason Knapp, one of the Phillies top pitching prospects, went on the DL yesterday with shoulder fatigue.  That could throw a monkey wrench into the works.

In recent days, the Angels and Cardinals have emerged as potential trade candidates for Halladay.  Rosenthal dispels the possibility that the Angels could land Halladay.  Sure, they have interest, but they don’t have the trade chips necessary to make the deal.

The Cardinals also have interest and they have top prospect Brett Wallace who the Blue Jays once coveted.  To make the deal even more appealing, Halladay and Cards ace Chris Carpenter are close friends.  The one sticking point for the Cardinals is that they don’t have the MLB-ready starter that the Blue Jays say they want as part of any package.  The Cards already have to send a pitching prospect to Cleveland to complete the Mark DeRosa deal, so they’re currently a bit thin on pitching prospects.

That’s where the Cubs come in.  Not only would it be great to add Halladay to the rotation, but it would also be important to keep him out of St. Louis.

The Cubs have the MLB-ready pitching that Toronto wants.  Any deal could include Sean Marshall or Randy Wells.  A deal would also likely include the Cubs top prospect, 3B Josh Vitters.  I know Cubs fans would hate to see him go, but trading a prospect (someone with the potential to be good someday) for the best pitcher in baseball seems like a good move to me.  Plus, the Cubs don’t have the greatest track record when it comes to developing prospects.  Consider that before Vitters took the title, the Cubs top prospects were Felix Pie (2006-07), Brian Dopriak (2005), Angel Guzman (2004), Hee Seop Choi (2003), Mark Prior (2002), and Corey Patterson (1999-2001).

Adding Halladay will obviously cost the Cubs money and prospects, but he’s the type of pitcher that can instantly turn around or solidify a rotation.  And unlike CC Sabathia was last year for the Brewers, Halladay is just a few month rental.  He’ll be around for at least a year-and-as-half and the Cubs will have first shot at signing him to his next contract.  A rotation in 2010 of Halladay, Zambrano, Dempster, Lilly, and either Marshall or Wells would be mighty nice.

As long as we’re dreaming, let’s dream big.  What if the Cubs were to pull the same type of stunt that Anthony Reber suggested the Yankees pull, namel trading for both Halladay and Vernon Wells.  The Cubs could send Marshall or Randy Wells to Toronto along with Vitters and Milton Bradley (one bad contract for another).  Sure, Vernon Wells is overpaid and signed through 2014, but he is a better CF than anyone the Cubs currently have, he’s hitting better than Bradley (even though he isn’t hitting that great), and he isn’t the distraction that Bradley is.  There’s a lot to like about this deal!

Okay, while this has been fun, let’s be honest.  The likelihood that the Cubs will be involved in the Roy Halladay sweepstakes, let alone land him, is remote.  My best guess is that if Toronto trades Halladay, he’ll end up in Philadelphia.  Unfortunately, I think the Cardinals are next in line should Philadelphia falter.  That could hurt. 

Hendry has pulled off some impressive trades in the past.  Can he somehow, some way work something out for Halladay?  Doubtful, but you never know.