Who is the only president to have someone elected after him and later be reelected?

That would be Grover Cleveland, the 22nd and 24th President of the United States, and the only one to date to serve two non-consecutive terms of office. Cleveland won his first presidential election in 1884. This was a bitterly contested affair against the Republican candidate James Blaine. The Republicans targeted Cleveland with personal abuse over an allegedly scandalous past involving the fathering of an illegitimate child. But Blaine himself had been dogged for many years by allegations of graft and corruption and the Democrats made a great play of this.
When the votes were counted, Cleveland won by a whisker—just one quarter of one per cent. The final tally in the electoral college was slightly more comfortable:219-182. Cleveland's first term was characterized by reform. In particular, his administration pursued a policy of tariff reduction, as most Democrats believed that the government should not take more money from the people than was strictly necessary for its maintenance. Opponents, however, favored a high tariff to protect American business from foreign competition.
Inevitably, tariff reform galvanized Republican opposition to the first Cleveland Administration and formed a central plank of the party's platform at the 1888 election. Hampered by an inept campaign, Cleveland lost the election to the Republican Benjamin Harrison. Though Cleveland narrowly won the popular vote, he lost in the electoral college.
The Harrison Administration pursued a controversial economic policy that involved increasing the amount of money in circulation backed by silver. This was intended to help farmers and other small businessmen to pay off their debts more easily. The downside was that it would lead to an increase in inflation and effectively reduce the value of the dollar. Cleveland felt passionately about the issue, so much so that it brought him out of semi-retirement. He once more entered the political fray and was chosen by the Democratic Party to be its candidate for the 1892 election.
The campaign was a low-key affair on account of President Harrison's wife dying of tuberculosis. Once again, tariff reform was a major issue, with growing numbers of voters sick of persistently high prices for imported goods which they attributed to the Harrison Administration's protectionist measures.
The Cleveland-Harrison rematch ended in victory for the Democrat, edging out his Republican opponent by three percentage points in the popular vote and a comprehensive 277-145 majority in the electoral college, with the remaining 22 votes going to the Populist candidate James B. Weaver.
https://www.history.com/topics/us-presidents/grover-cleveland


Grover Cleveland is the only president to have served two nonconsecutive terms. Defeating James Blaine in 1884, Cleveland was elected the first Democrat president following the Civil War. As Governor of New York when he began his campaign, Cleveland gained leverage after Blaine’s “Mulligan Letters” revealed corruption. The news of this conspiracy to extend federal favors to a southern rail company encouraged many Republicans to switch to the Democrat Party. Such party disloyalty, based on moral grounds, earned these new Democrats the unsavory title of Mugwumps (a term used to describe someone with a "holier than thou" attitude). Cleveland served as the twenty-second president of the United States from 1885 to 1889. In 1888, Cleveland lost the twenty-third presidency to Benjamin Harrison. Cleveland did win the popular vote; however, Harrison held 58.1% of the electoral vote. In 1892, the resilient Cleveland ran again, defeating Harrison and becoming the twenty-fourth president of the United States of America (1893–97).

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