The cubs have won 44 baseball games and have lost 65 games. they have 53 games remaining. at least how many of the remaining 53 games must the cubs win to have a winning season? (a winning season means they win more than 50% of their games.)

More than 50% would be 50% of the total games plus one win.
In total, there are 162 games.
44+65+53=162
50% of 162 equals 81.
The cubs must win 82 games. If they have won 44 games so far, then 82-44=36
They must win at least 56 games to have a winning season.

Hope I got it right for your sake.