Chicago Experts Weigh In On Trump Campaign Shakeup

(CBS) – The Donald Trump campaign has been rebooted yet again.

The former campaign chairman is out and new campaign ads are on the air.

Two Chicago-based campaign veterans spoke with CBS 2 Political Reporter Derrick Blakley about whether the latest shakeup can right the ship for the Republican.

"These kinds of things are usually ironed out typically in the primary," Democratic strategist Kevin Conlon says. "It's very, very unusual to have things -- 2 or 3 major changes -- within 100 days of a November election."

Conlon has advised White House candidates from Howard Dean to Hillary Clinton and instability this late is a harmful distraction.

"The focus always has to be on the campaign, the candidate, and not the intramurals and the infrastructure piece of it."

Chip Englander managed Republican Bruce Rauner's campaign for governor and Rand Paul's unsuccessful presidential bid. He says the message is Trump wants to be Trump.

"He hasn't looked particularly constrained to me. But obviously he felt he was being put in a box and maybe this will unleash him. It will be exciting for people who enjoy watching this. It's the circus, for sure."

Trump began airing his first TV spots in battleground states today. Englander says Trump's late campaign shakeup isn't promising.

"Whenever you see something like this, it usually does not end well," he says.

Trump's hoping to overcome a torrent of Clinton TV ads, with giant rallies and sheer force of personality on free media, he says. But that will only work if trump stays on message, which so far, he's been unable or unwilling to do.