Woolson was at the center of Huckabee's stunning victory in the 2008 Iowa caucuses and his decision to switch camps will be read as an indication that the former Arkansas governor is leaning against a return run for president.
Huckabee allies insist that idea is misguided, noting that while Woolson was a trusted ally in 2008, he is not part of the governor's inner circle as he decided about whether or not to run in 2012.
Huckabee, however, has expressed his own reservations about a second national bid of late, telling the Post's Karen Tumulty that "I'm not one who thinks the future of the world is depending on whether I run for president".
Woolson's hire is also a sign of Pawlenty's big bet on Iowa where his team clearly believes he must win -- or perform above expectations in order to have a real shot at the Republican nomination.
Woolson, who served as communications director in Iowa for the caucus campaign of then Texas Gov. George W. Bush in 2000, will join Annie Kelly on Pawlenty's Iowa team. Kelly, who served as deputy campaign manager for Pawlenty's 2006 gubernatorial race and ran his Freedom First PAC, moved to Des Moines a few weeks ago.
And, Pawlenty has several other Iowa aces up his sleeve -- most notably Terry Nelson who, for a time, managed John McCain's 2008 presidential campaign, and former Bush White House political director Sara Taylor. Both are Iowa natives.
There has been very limited polling done in Iowa but Pawlenty remains far behind better known candidates like Huckabee and former Govs. Mitt Romney and Sarah Palin.
But, Pawlenty is lavishing the Hawkeye State with attention -- he spoke at a candidate cattle call sponsored by the Faith & Freedom Coalition earlier this week and will be back for another forum later in the month -- and is hoping that his Midwestern roots and average Joe pitch resonate with Iowa voters.