He was elected mayor of Janesville in April 1885 for a two-year term, over Republican
Charles Valentine. He was elected to the Assembly as a Democrat again in 1886, after being defeated in a run for the United States Senate by incumbent Republican
Philetus Sawyer, who won the votes of 82 legislators, to 37 for Winans and six for
Populist John Cochrane. For the Assembly, he received 1,132 votes to 1,047 for Republican Oscar Nowland (Republican incumbent
Pliny Norcross was not a candidate) and 91 for Prohibitionist James Harris. When the Assembly session opened, he was the Democratic candidate for Speaker, losing to Republican
Thomas B. Mills in what turned out to be a six-man race. He once more returned to the judiciary committee, and to the committee on bills on the third reading. He was not a candidate for re-election in 1888, and was succeeded by Republican
Cyrus Miner. He was elected to the Assembly (as a Democrat) for the final time in 1890; the 2nd district no longer included the Town of Rock, but did include those of
Center and
Harmony. He received 1487 votes to 1308 for Nowland and 67 for Prohibitionist C. W. Cook. He again became chair of the judiciary committee; and was also on the
joint committees on
charitable and
penal institutions, and on
apportionment (serving as Assembly co-chair of the latter committee). After the
redistricting of 1891, most of his district was put in the new 3rd Rock County Assembly district; Winans did not run for re-election, and was succeeded by fellow Democrat
Agesilaus Wilson. == Out of office again ==