<style>
.columns {
  width: 250px;
  column-width: 250px;
  height: 160px;
  font-size: 22px;
}
img {
  float: left;
  background-color: red;
  width: 100px;
  height: 100px;
}
.widower {
  orphans: 1;
  widows: 2;
}
</style>
<div class="columns">
  <div class="first">first<br>second<br>third<br>fourth<br><img></div>
  <div class=widower>PASS if this text does not overlap the red box on the second column.</div>
</div>