A lot of attention has been paid to the possibility of Zach Randolph being traded this offseason from Portland, now that Greg Oden is on the horizon.  While this would seem to make sense from Portland's point of view, the reality is that Randolph has one of the most untradeable contracts in the league, even for a young All-Star talent (and this doesn't even include his "character issues").

The Knicks supposedly have some of the most untradeable contracts in the league, in Stephon Marbury ($42,000,000 over the next two years), Steven Francis ($33,620,000 over the next 2 years), and Malik Rose ($14,748,750 over the next two years).  Reality check: as bad as all three contracts appear, they are still better than Randolph's, and more likely to get traded (which isn't to say they will get moved, just that they are easier to move).   Here's why:

The Greatest NBA Free Agent Class Ever.  Coming after the 2009/2010 season.

Let's start there.  LeBron James' contract expires after the 2009/2010 season.  He has a player option for 2010/2011 (at slightly more than $16 million), but there really isn't any reason to exercise it - he can get a brand new contract for more money, either from the Cavs or from anyone else.  Of course, he'll probably only be interested in signing with three teams - the hometown Cavs, the Brooklyn Nets (J-Hova!), or the long-shot Knicks.  Everyone else shouldn't waste their time.  The only reason we can think of that LeBron might exercise his option for 2010/2011 is if he thinks the Cavs can win it the next season (presuming he hasn't won it all already at that point), and wants to give it a go before switching teams (again, if he's going to stay in Cleveland, he can just go for the big contract from them at that point).  

But LeBron isn't the only premier player whose contract is scheduled to expire at the end of 2009/2010.  Check out this list:

Joe Johnson, Atlanta
Ben Wallace, Chicago
Larry Hughes, Cleveland
Zydrunas Ilgaukas, Cleveland
Josh Howard (Team Option for 2010/2011, very affordable, so unlikely to be free)
Dirk Nowitzki (player option for 2010/2011, for $21,513,524, unlikely to opt out)
Rip Hamilton, Detroit
Al Harrington, Golden State
Stephen Jackson, Golden State
Tracy McGrady, Houston
Rafer Alston, Houston
Jermaine O'Neal, Indiana
Cuttino Mobley, LAC
Tim Thomas, LAC
Kobe Bryant, LAL (player option for 2009/2010, 2010/2011)
Mike Miller, Memphis
Shaquille O'Neal, Miami
Dwayne Wade, Miami
Bobby Simmons, Milwaukee
Andrew Bogut, Milwaukee
Charles Villanueva, Milwaukee
Chris Paul, New Orleans
Quentin Richardson, NYK
Jerome James, NYK
Hidayet Turkoglu, Orl
Amare Stoudemire (player option, underpaid)
Steve Nash
Raja Bell
Darius Miles
Brad Miller
Shareef Abdul-Rahim
Kenny Thomas
Tim Duncan
Emanuel Ginobili
Ray Allen
Earl Watson
Luke Ridnour
Chris Bosh (player option, underpaid)
TJ Ford ($8,500,000 player option, hard to tell if that is a good deal for him or not)
Carlos Boozer (can opt out in 08/09)
Mehmet Okur (can opt out in 08/09)
Deron Williams
Marcus Camby
Marquis Daniels
Andrew Bynum
Udonis Haslem

Okay, let's take a step back.  First off, Jerome James was a joke.  He's not a premier free agent, though we wouldn't be surprised if he somehow got another multi-year contract.  But here is that list again, in terms of big All-Stars/franchise players only: Joe Johnson, Rip Hamilton, T-Mac, Jermaine O'Neal, Kobe (possible), Shaq, Wade, Paul, Amare, Nash, Duncan, Ginobili, Bosh, Boozer, Deron Williams, Ray Allen.  Not all of those will make it to free agency, of course, but more than you might think will - Boozer is underpaid.  Duncan ain't leaving SA, but Ginobili might be let go.  Wade, Paul, Amare, Williams, Bynum and Bosh are all young enough to land a franchise player contract anywhere they want.  So maybe Bosh is tired of Canada, eh?  

That list also includes a lot of aging vets looking for a title run (Wallace, Nash, Allen) and missing piece/2nd banana types (Ginobili, Tim Thomas, Hughes, S-Jax, Mike Miller, Brad Miller, Okur, Haslem.

Also worth noting: The 2008/2009 expiring contracts:

Andre Iguodala (rookie contract)
Andre Miller
Stephon Marbury
Steve Francis
Malik Rose
Shawn Marion
Mike Bibby
Kevin Martin (rookie contract)
Jorge Garbajosa (rookie contract)
Carlos Boozer (can opt out in 08/09)
Mehmet Okur (can opt out in 08/09)
Gilbert Arenas
Josh Smith (rookie contract)
Al Jefferson (rookie contract)
Emeka Okafor (rookie contract)
Ben Gordon (rookie contract)
Drew Gooden
Allen Iverson
JR Smith (rookie contract)
Rasheed Wallace
Baron Davis
Andris Biedrins (rookie contract)
Elton Brand (player option for 08/09, so could expire 07/08)
Corey Maggette (player option for 08/09, so could expire 07/08)
Shaun Livingston (rookie contract)
Lamar Odom
Kevin Garnett (player option for 08/09, so could expire 07/08)
Jason Kidd
Nenad Krstic
Dwight Howard (rookie contract)
Jameer Nelson (rookie contract)

Okay, too many of those rookie contracts (AI2, Howard, K-Mart, Josh Smith, Al Jefferson, Okafor and probably Gordon) are unlikely to switch teams as free agents.  Still, you have All-Stars Baron Davis, Rasheed Wallace, Allen Iverson, Marbury, Mike Bibby, Andre Miller (lots of PGs), Marion, Arenas, Kidd, Garnett and Brand.  That's the front year of back to back years of amazing free agents.

To compare, look at the class of 06/07: Vince Carter, Grant Hill, Chauncey Billups, Gerald Wallace.  One All-Star with a terrible rep, one aging, oft-injured veteran who  will probably command a mid-level exception on a contender, one vet who is unlikely to leave his team (Billups), and only one young talent who might switch teams.  

The 07/08 class?  It goes: Antawn Jamison, Michael Finley, Sam Cassell.  Maybe Garnett, Brand and Maggette, if all three decide to opt out early.  Note that all three are paid well, so are in a similar situation to Jamison this year, in which Antawn is more likely to exercise the option and play for another year at the high salary rather than to opt for free agency and possibly get less money.  So despite the options, we think Garnett, Brand and Maggette are unlikely to opt for free agency, making 07/08 a really bad year for free agents. 

The point of this post: Well, given that most teams have GMs smart enough to be aware of this, most are planning for the 08/09 and 09/10 free agent classes by leaving cap space available to sign free agents.  Which makes any player with a big  (read: overpaid) contract that runs through 10/11 or more very much out of demand.  Enter Zach Randolph ($17,333,333 for 2010/2011) and his ilk.  

Contracts that run until 2010/2011:
Paul Pierce ($21,513,521)
Kirk Hinrich (9,000,000), plus 8,000,000 (2011/2012)
Erick Dampier (13,075,000)
Jason Terry (10,650,000) plus 11,437,500 (2011/2012)
Kenyon Martin (16,545,454 player option)
Nene (14,200,000)
Carmelo Anthony (16,378,325), plus option for 2011/2012 (17,686,100)
Reggie Evans (5,080,000)
Tayshaun Prince (11,148,760)
Nazr Mohammed (6,883,800)
Jason Richardson (14,444,444)
Shane Battier (7,354,500)
Yao Ming (17,040,000)
Troy Murphy (11,968,253)
Mike Dunleavy (10,561,984)
Jamaal Tinsley (7,500,000)
Chris Kaman (11,300,000) plus for 2011/2012 (12,200,000)
Vladimir Radmanovic (6,883,800 player option)
Pau Gasol 17,822,187
Michael Redd 18,300,000 (player option)
Dan Gadzuric (7,243,750)
Marko Jaric (7,625,000)
Richard Jefferson (15,000,000)
Predrag Stojakovic (15,336,000)
Tyson Chandler (12,750,000 player option)
David West (8,287,500), plus option for 2011/2012  (7,525,000)
Eddy Curry (11,276,863 player option)
Jamal Crawford (10,080,000 player option)
Jared Jeffries (6,883,400 player option)
Samuel Dalembert (12,200,000)
Kyle Korver (5,536,303)
Boris Diaw (9,000,000) plus player option for 2011/2012 (9,000,000)
Leandrinho Barbosa (7,100,000) plus player option for 2011/2012 (7,600,000)
Zach Randolph (17,333,333)
Joel Przybilla (7,405,300)
John Salmons (5,808,000)
Tony Parker (13,500,000)
Nick Collison (6,750,000)
Andrea Bargnani (8,485,738)
Andrei Kirilenko (17,822,187)
Caron Butler (10,561,960)

Some of these contracts are good deals, relative to the skill level of the player; these are the ones you rarely hear mentioned in trade talks:  Kirk Hinrich, Barbosa, Carmelo, Yao.  Even Tayshaun Prince and Eddy Curry are okay, as they are under $12,000,000 each.  Richardson is the start of the borderline "untradeable" contracts - given his knee injury, he might be too much of a risk at almost $15 million (or about 1/4 the expected cap in 2010/2011). 

Others are definitely very much a tough cap eater, and their names are often floated in trade talks: Randolph.  Pierce.  Jefferson.  Guys that no one even bothers to mention anymore, because no one wants them:  Dampier.  Murphy.  Kenyon Martin.  Dunleavy.  Jaric.  Kirilenko (a good player, but not a franchise player - you can't give $17 million to a guy who can't score or carry your offense).  Stojakovic.  Redd.

So, despite all the talk about what Portland should do with Randolph ("trade him for the #3 pick!"), the reality is this: Unless they really make it worth someone's effort, like include at least Jarrett Jack and probably more (maybe a future #1, maybe Webster), the only way a team accepts Randolph is if they are getting rid of one of the monster contracts themselves - Paul Pierce, anyone?  Actually, that might make sense for both teams....

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