Four years after his unsuccessful bid to help Raila Odinga succeed him as President, some observers argue that his latest political calculations could be facing fresh headwinds.
Uhuru has endorsed former Interior CS Fred Matiang'I as Jubilee Party's preferred presidential prospect.
Political commentator Caleb Burudi believes Jubilee should be cautious about settling on Matiang'i as its presidential candidate before broader consultations in the opposition coalition.
He says the party risks repeating past mistakes if it assumes Matiang'i is the automatic choice to fly the coalition's flag.
"While Matiang'i is widely recognised for his record in public service, a presidential campaign requires broader political networks, grassroots mobilisation and the ability to build a coalition that extends well beyond a candidate's regional base," Burudi said.
He argued that the opposition's immediate priority should be building a united front capable of attracting support across the country rather than rallying behind a single individual too early. Burudi warned that prematurely endorsing one candidate could alienate other influential leaders and weaken efforts to mount a formidable challenge against President William Ruto in 2027.
The comments revive memories of the 2022 General Election, when Uhuru threw his full weight behind then ODM leader Raila after ending his political alliance with William Ruto, who was his deputy.
The endorsement followed the 2018 Handshake between Uhuru and Raila, which gave rise to the Azimio la Umoja-One Kenya Coalition.
Throughout the campaign, Uhuru argued that Raila was best placed to preserve national unity, sustain economic development and continue key government programmes. Despite the backing of the outgoing President and a broad coalition of political parties, Raila narrowly lost the election to Ruto.
According to the IEBC, Ruto garnered 7,176,141 votes, representing 50.49 per cent of the total vote, while Raila secured 6,942,930 votes, or 48.85 per cent. The Supreme Court later upheld Ruto's victory after dismissing Raila’s petition challenging the presidential results.
With attention now shifting to the 2027 race, Uhuru has focused on rebuilding Jubilee Party after its diminished performance in the last election.
The former President has overseen efforts to reorganise the party's structures, with Matiang'i emerging as the figure many Jubilee leaders view as the party's best hope of returning to national prominence.
However, political developments in Kisii Nyanza, widely regarded as Matiang'i's political backyard, have complicated that strategy. A growing number of regional leaders have recently appeared at Nairobi Senator Edwin Sifuna's Linda Mwananchi rallies. This has fuelled speculation that Sifuna is steadily expanding his influence in the region.
Among those who have openly associated themselves with Sifuna's movement is Kisii Senator Richard Onyonka, who has publicly endorsed the Nairobi senator's possible presidential bid. Kitutu Masaba MP Clive Gisairo has also participated in political engagements alongside Sifuna during tours of the Gusii region.
The shifting alliances have been further highlighted by the resignation of former Jubilee official Pauline Njoroge from the party before joining Sifuna's political camp.
The development has intensified debate over Jubilee's ability to retain key allies as the opposition begins positioning itself for the next presidential contest.
Jubilee's recent electoral performance has also raised concerns about the party's ability to mount a national comeback. In the Ol Kalou parliamentary by-election, Jubilee candidate Wilson Kigwa managed only 198 votes, finishing far behind DCP's Sammy Kamau, who polled 35,440 votes, and UDA's Samuel Muchina Nyagah, who received 5,450 votes.
The result reinforced perceptions that Jubilee continues to struggle in areas once considered part of its political stronghold.
The outcome prompted fresh criticism from political leaders. Eldas MP Adan Keynan argued that the by-election demonstrated how dramatically the political landscape in the Mt Kenya region had changed.
Declaring Rigathi Gachagua the region's new political leader following the DCP victory, Keynan said the Ol Kalou seat had historically belonged to Jubilee but that the party had effectively been displaced.
He described the defeat as a wake-up call for Jubilee's leadership as it seeks to rebuild ahead of the 2027 General Election.
