Can Jon Daniels and Nolan Ryan find enough arms to allow the team to contend in 2009? If history is any indication, the answer is…no.

To be fair to Daniels in particular, the Rangers have a long, sad history of ill-fated signings and luckless trades, and his predecessor (John Hart) was much, much worse. Still, even a successful deal such as landing All-Star Josh Hamilton is mitigated by the loss of Edinson Volquez in that very same transaction.

So which are the worst deals of the Daniels regime?

Here’s our take, with marginal players omitted for the sake of brevity:

Alfonso Soriano for Brad Wilkerson, Armando Galarraga and Terrmel Sledge (2005): In essence, the Rangers completed the process of turning Alex Rodriguez into a light-hitting outfielder/first baseman (Wilkerson) who is no longer with the team.

And this one actually gets worse. To make room for the since-injured Jason Jennings, the Rangers traded Galarraga to the Tigers before the 2008 season in what amounted to a release. Galarraga won his 12th game on August 19, beating the Rangers in Arlington. Ouch!

John Danks for Brandon McCarthy (2006): Deeming their former No. 1 draft pick not quite ready for the bigs, the Rangers shipped him to the White Sox for the supposedly more seasoned McCarthy. Danks is an integral part of a contending team’s rotation; McCarthy has spent more time in the training room than on the mound.

Chris Young and Adrian Gonzalez for Adam Eaton and Akinori Otsuka (2006): Young won 24 games with an ERA under 4.00 in his first two seasons in San Diego. Considered too light of stick to play a corner infield position, Gonzalez hit 82 home runs in his first 442 games as a Padre. Eaton, meanwhile, left Texas after pitching just 13 lackluster games in 2006. Otsuka had 32 saves for the Rangers in 2006, but missed part of last year and all of this year with injuries.

Signing Kevin Millwood (2006): It’s not so much the concept here as it is the cost. Desperate for anything resembling a staff anchor, the Rangers ponied up $60 million over five years for a then-31-year-old pitcher who had won just nine games in each of the previous two seasons. After notching a respectable 16 wins in 2006, Millwood has been hurt for long stretches of the past two seasons…and he still has two more years on that inflated deal.

Re-signing Vicente Padilla: After being acquired from the Phillies, Padilla won 15 games for Texas in 2006, but proved to be a challenging clubhouse presence. Again, desperation was the mother of invention, and Padilla responded to a three-year, $34 millon free agent deal by winning six games in 2007. He bounced back a bit in ‘08 but faded after a strong start.