In the early going, Rick Perry’s top challenger for the 2016 GOP presidential nomination won’t be any of the other Republican candidates. It will be Mr. Perry himself.

In August of 2011, the then-governor of Texas jumped into the 2012 presidential race late, fresh off back surgery, and, Perry admits, ill-prepared. A few months later, he uttered the “oops” heard ‘round the world in a debate, when he couldn’t remember the third government agency he would abolish. Early in 2012, he dropped out of the race.

On Thursday, Perry will announce his second bid for the presidency. His first task: overcoming his embarrassing first campaign.

“He starts off behind the starting line; he’s got a lot to prove,” says Bruce Buchanan, a political scientist at the University of Texas in Austin. But “I can say that he’s worked pretty assiduously to try to get up to speed on the issues this time. He shows no sign of quit, and he’s been able to marshal his financial supporters.”

Still, Mr. Buchanan adds, “it’s going to be an uphill slog.”

Since last year, Perry has stressed that he’s been doing his homework ahead of a possible second presidential run.

“Over the past 18 months, I have focused on being substantially better prepared,” Perry told reporters last June at a luncheon hosted by The Christian Science Monitor.

More recently, since leaving the governor’s office in January after a record 14 years, Perry has laid out a rationale for a campaign. He has positioned himself as a pragmatic executive willing to compromise – and an outsider who can bring change to a gridlocked capital.

Washington “has become a debating society that seldom solves problems,” Perry told the American Principles Project in Washington in February, according to Politico. “Governors have to make choices and take action. Americans have become cynical that Washington can ever change. And I am skeptical that an agent of change can come from Washington.”

Perry appeared to take aim at fellow Texan Ted Cruz, a hard-line conservative senator who is also running for president. “We must remember we are not electing a critic-in-chief, we are electing a commander-in-chief,” Perry said.

Henry Barbour, Republican national committeeman from Mississippi and an informal adviser to Perry for the past few years, says Perry’s path to the nomination doesn’t run through competing in any “brackets” or going after particular candidates, but in touting his record and his issue positions.

“The country is hungry for some performance out of the White House. We’ve had enough of hope and hype,” says Mr. Barbour in an interview. “Rick Perry brings record job growth, population growth, serious education achievements, and record graduation rates of minorities in Texas. There’s been a lot of success.”

“Plus, he’s authentic,” Barbour adds. “That’s another contrast to President Obama and Mrs. Clinton.”

Unlike most in the Republican field, Perry brings military experience to the table. He served five years in the 1970s as a pilot in the Air Force, attaining the rank of captain. Sen. Lindsey Graham (R) of South Carolina, who announced for president on Monday, is the only other veteran running. He served as a judge advocate in the Air Force during the 1980s.

Perry’s military service could be a key argument to Republican voters, says GOP pollster Kellyannne Conway.

"More than any election since 1980, 2016 will be a national-security contest,” Ms. Conway told CNBC’s Larry Kudlow in March.

In his speech to the Conservative Political Action Conference in February, Perry called for a more muscular foreign policy, warning that the Islamic State represents “the worst threat to freedom since communism.”

Right after he delivered his speech, his leadership political action committee, RickPAC, released an ad touting Perry’s military service.

University of Virginia political scientist Larry Sabato notes Perry’s “strong campaign team” as an advantage. In addition to Barbour, Perry has signed on Steve Schmidt, a former top aide to 2008 GOP nominee John McCain. Mr. Barbour’s brother, Austin, another top GOP strategist in Mississippi, is leading Perry’s super-PAC, the Opportunity and Freedom PAC.

Together, the Barbour brothers (nephews of former Gov. Haley Barbour (R) of Mississippi) were instrumental in fending off a strong tea party challenge to Sen. Thad Cochran (R) of Mississippi last year. Tea party activists are furious over Perry’s association with the Barbours and Mr. Schmidt, but it’s not clear how powerful the tea party “establishment” will be in the 2016 cycle.

In the end, the success or failure of Perry 2.0 will rest squarely on the candidate himself. He starts with strong speaking and fundraising skills. Perry has recruited major donors to RickPAC, including some of the biggest fundraisers in Republican politics, according to The Washington Post.

Perry also has built networks of supporters in the early nominating states, Iowa, New Hampshire, and South Carolina, which he didn’t do in 2011. And he’s skilled on the stump.

“He’s a very good platform performer,” says Buchanan from the University of Texas. “He’s got as much going for him as a great lot of the rest of the mob on the Republican side.”

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But that points to a major problem: the size of the GOP field, which could approach 20 people when the announcements are done. This field is also stronger than in 2012. As a prospective candidate, Perry has been polling down in the pack, in 10th place, according to the Real Clear Politics average. If he can stay in the top 10, he will qualify for the first debate on Aug. 6. But if he drops below 10th , that could kill his chances before the campaign really starts.

That’s why the next two months are critical. Perry needs to build his national name recognition, and get his message out – that, in his view, he successfully governed the second-largest state for 14 years. There may also be comparisons to the last Texas governor to win the presidency: George W. Bush. But while that was viewed as a liability for Perry in 2012, it may be less so in the 2016 cycle, as time has softened memories and former President Bush’s favorability ratings have improved.