This profile is part of our 2018 Power Issue. For more of 2018's most powerful Texans, click here.

Randall Stephenson has emerged as an unlikely media mogul. A phone-company lifer, the 58-year-old AT&T honcho has taken on the task of turning stodgy old Ma Bell into an entertainment diva by paying $85.4 billion to acquire Time Warner, the media powerhouse that owns HBO, CNN, and Warner Bros. Pictures. Combined with a $67 billion deal for DirecTV in 2015, the purchase moves the 139-year-old company rooted in landline monopolies into the era of cord-cutting and streaming content.

At least, that’s the plan. There are strong headwinds working against Stephenson’s vision. The federal government opposed the Time Warner deal when it was announced and recently appealed a judge’s approval of the merger. (It’s unclear if the decision was influenced by Stephenson’s strained relationship with President Trump, a frequent critic of CNN.) And while the DirecTV purchase significantly increased AT&T’s subscriber base, some analysts argue that Stephenson paid too much. Millions of Hulu- and Netflix-loving customers have defected from satellite TV and switched to providers that offer high-speed internet connections that AT&T has lagged in offering. (It’s currently expanding its AT&T Fiber service in several major Texas cities.)

And then there’s the issue of debt. Since becoming CEO in 2007, Stephenson has embarked on a buying spree somewhere in the neighborhood of $300 billion, leading to a whopping $190 billion in red ink for the Dallas-based company—more than the national debt of some countries. That could pose problems for AT&T if the debt markets head south.

But thanks to AT&T’s vast asset base and profitable businesses—the company expects to throw off as much as $10 billion in free cash flow annually with the Time Warner deal—Stephenson probably isn’t terribly worried. For years he has kept a color-coded list of potential acquisitions that he updates frequently, a habit he learned from his onetime mentor, the vastly wealthy Mexican businessman Carlos Slim. While Stephenson won’t reveal what companies are on the list, it’s a safe bet that he hasn’t scratched off his last target.

This article originally appeared in the December 2018 issue of Texas Monthly with the headline “Dragging AT&T into the Twenty-First Century.” Subscribe today.