Even since he was fielded by the Congress from a seat first nursed by Jawaharlal Nehru, Kaif has had to face the lack of support from old party hands. His hurriedly put together squad also lacks experience.
In short, according to those monitoring the Phulpur constituency, some 220 km from Lucknow, Kaif's team is in disarray.
"Support can only take you so far. Once you cross the line, you have to face the bowler alone," the 33-year-old Kaif told IANS, obliquely hinting that not all was well with his campaign.
The Phulpur seat covers five assembly constituencies, two of them falling in Allahabad city, and is home to 17.36 lakh voters.
In 2009, the seat went to Kapil Muni Karwariya of the Bahujan Samaj Party (BSP). The Congress won it last in 1984 and has since then not even been a runner up.
In the last election, it finished third. The party's then candidate Dharam Raj Singh Patel is now with the Samajwadi Party and is again in the fray.
Another formidable opponent is Keshav Prasad Maurya of BJP who is buoyed by the "Modi wave" and by the party's alliance with the Apna Dal which has influence over the two lakh Patel votes.
Kaif's biggest drawback are his inadequacies in his maiden electoral battle.
Unlike most candidates, he has avoided addressing public meetings, relying more on door-to-door canvassing.
Santosh Gupta, the 30-year-old owner of an advertising agency who heard one of Kaif's rare speeches dubbed it as "very disappointing" because he had "nothing important to say".
"This constituency has a legacy... How can someone like Kaif be the right choice? A cricketing hero cannot be a hero everywhere," says Gupta.
Kaif, who is from Allahabad, is a Class 12 passout whose cricketing talent hit the spotlight when he led the under-19 team to a World Cup victory in 2000.
His most memorable turn happened in the 2002 Natwest Series in England, after which he was in and out of the Indian cricket team. He has not played for the country since 2006.
Kamal Kishor, a photographer who lives close to Kaif's home in Civil Lines area, says Kaif supporters - mainly some sportspersons - have been getting into scuffles with the opposition.
"No one really seems to know what is happening with Kaif's campaign," he says.
Congress sources say the leading cricketers Kaif said would bat for him haven't visited the constituency.
Even Kaif fans are disappointed.
Mohammed Arif, a 22-year-old engineering student, says: "There was a general excitement when his name was announced. But I haven't seen him come asking for votes."
But Brijendra Singh, a political writer, believes that with Kaif around, the Congress is at least figuring in the contest.
"Had the party fielded anyone else, it would have lost its (security) deposit. Now some young people will vote for him."
Kaif believes this as much.
"Young people are looking at me with a lot of hope," Kaif told IANS. "Nothing has happened in the constituency for so years. People know that I will be as sincere as a politician as I was as a cricketer."
Kaif is contesting from Phulpur, which was first nursed by Jawaharlal Nehru
What if he loses? "Cricket has made me mentally tough," Kaif says. He will need his mental toughness when Phulpur votes Wednesday.
The opposition is of course less charitable.
BJP candidate Keshav Prasad Maurya told IANS: "He may be a good player but this is a different game."