JSFiddle - React, Tailwind, and code Playground

HTML

<div class="list-group-item">
    <h4>Short item</h4>
    <p>I don't have that much content really</p>

    <div class="ribbon">
        <span>Ribbon</span>
    </div>
</div>
<div class="list-group-item">
    <h4>A much longer item</h4>
    <p>I have a lot of content, because I have a Lorem ipsum in me</p>
    <p>Lorem ipsum dolor sit amet, consectetur adipisicing elit. Dignissimos amet, minus maiores adipisci. Neque possimus, iusto odio explicabo. Libero, fugiat.</p>
    <p>Lorem ipsum dolor sit amet, consectetur adipisicing elit. Ipsam, aliquid.</p>
    <p>Lorem ipsum dolor sit amet, consectetur adipisicing elit. Dignissimos amet, minus maiores adipisci. Neque possimus, iusto odio explicabo. Libero, fugiat.</p>

    <div class="ribbon">
        <span>Ribbon</span>
    </div>
</div>

CSS

.list-group-item {
    position:relative;
    padding:20px;
    padding-left:60px;
    border:1px solid #ccc;
}
.ribbon {
    position:absolute;
    top:0;
    left:0;
    width:40px;
    height:100%;
    background:blue;
    color:white;
}
.ribbon span {
    display:block;
    top:20%;
    left:0.6em;
    position: relative;
    -ms-writing-mode: tb-rl; /* old syntax. IE */
    -webkit-writing-mode: vertical-rl;
    -moz-writing-mode: vertical-rl;
    -ms-writing-mode: vertical-rl;
    writing-mode: vertical-rl; /* new syntax */
    -webkit-text-orientation: upright;
    -moz-text-orientation: upright;
    -ms-text-orientation: upright;
    text-orientation: upright;
}