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Raila's weaknesses according to insiders

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Those who know Raila intimately say his biggest weaknesses are:
1. INABILITY TO TAKE ADVICE
Raila tends to listen to very many people but often, his mind is made up even as he listens. He will listen but still go back to his old ways. That means no new thinking enters his stream.
2: FAITHFULNESS TO FRIENDS
Unlike most politicians, Raila does not know how to let go of old friends who have become a liability. Many view the likes of James Orengo, Jakoyo Midiwo, and Oburu Oginga as spent forces with no new ideas to offer. Nyong'o has eased himself out of Raila's circle although he remains an intellectual force and part of the ODM think tank. Politically, Nyongo is concentrating on Senate duties and campaigns for Kisumu governor. Orengo on the other hand remains a constant around Raila and many view him as a bad influence who pushes out people with new ideas. He seems to believe that those who did not participate in the events of the 1980s and 1990s have nothing to offer. Raila seems not to know how to discard him. Orengo, alongside Muthama, is
currently being blamed for the failure by Okoa Kenya to raise sufficient signatures. Problems began when he and Muthama declared themselves in charge and made Okoa Kenya a CORD affair. These old friends let him down big time in Bomas in 2013 where the chief agent was either missing at critical moments of tallying or asleep or unavailable.
3: DISORGANISATION
In the 2013 elections, Raila campaign had as many as five or more tallying centres. That was a recipe for chaos. It was a manifestation of Cord's lack of leadership. Poor coordination also made agents miss their pay. Caroli Omondi was in charge of both the agents and setting up of tallying centres, most of which never worked.
4:BELIEF IN A FAIR CONTEST AND A KENYA THAT MIGHT BE
Raila admires nations where current and former Presidents live in complete harmony, where former leaders are accorded respect and given a role during national functions. He talks fondly of how the US parades its current and former leaders at critical national events and even in times of crisis. He admires this about Nigeria and Tanzania. He believes it can happen in Kenya. This partially informed his approach to the 2007 elections.
Despite indications that Kibaki was marshalling institutions, including police, to cling on to power, Raila believed that Kibaki would facilitate a fair contest and concede defeat. He did not believe that Kibaki would be keen to see the alternative which would be chaos.
5: FAITH IN INSTITUTIONS AND LAWS
This is what messed Raila up most in 2013. Having fought for a new constitution and presided over its promulgation in 2010, Raila believed the new laws and the supposedly independent and strong institutions it created would be enough to safeguard the vote. He believed the new institutions like the IEBC, police and top public servants, having undergone rigorous vetting, would stand up for the country and ensure free and fair polls. Raila did not believe these same institutions could be manipulated and that the officers who had been vetted, some on his recommendation, could mismanage the vote. In addition, he seemed to believe that with the 2007-2008 election chaos still fresh in people's minds, no one would be reckless enough to do things that might take the country back to chaos. He trusted that everyone would do good.
6: FAILURE TO DELEGATE
This has seen Raila make some very erroneous
appointments. Rather than create an institution and team to vet appointees and potential appointees, he likes to do it himself. The effect is that anyone with Raila’s number can call him, set up a meeting and sell himself as good in this or that. That is how he has ended up picking up a number of people: Tony Gachoka, Magerer Langat, Ngunjiri Wambugu, Eliud Owalo, among others. There were questions how Owalo was picked among so many potential campaign managers to head Raila's campaign in 2013, or how Caroli Omondi ended up being Raila’s Chief of Staff out of the many people who had worked with Raila over the years and who knew his thinking and his friends. Raila met these people, interviewed them secretly, and appointed them.
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