Trump's strategy: Where he says he can win

By Gregory Wallace, CNN

Updated May 27, 2016

Donald Trump is not a conventional politician.

And his path to the White House may not be very conventional either.

He's hinting at a path to 270 electoral votes that would redraw the electoral map, taking him to victory through some states that haven't gone Republican since George H.W. Bush nearly swept the map in his 1988 bid.

Presidential nominees typically focus on a handful of so-called battleground states, those that political observers and campaign strategists believe can tip either way in November. They largely take for granted that the rest of the map is predictable -- Texas for Republicans and California for Democrats, for example.

But Trump has claimed he can shake up that math by winning least eight states that CNN has categorized as either likely or solidly Democratic.

He's also projected confidence he'll pocket Florida and Ohio. Those states are historically the two most hotly-contested battlegrounds and are the largest prizes among the nine toss-ups on this year's map.

Solid Republican

West Virginia

Last Republican win: 2012

5 electoral votes

"We're going to win West Virginia big."
Trump on NBC, 1/15/2016

Battleground

Florida

Last Republican win: 2004

29 electoral votes

"We're going to win Florida."
Trump on NBC, 1/15/2016

Ohio

Last Republican win: 2004

18 electoral votes

"Ohio is going to remember that I stuck up for Cleveland (where Republicans will hold their convention)."
— Trump, 5/26/2016

Lean Democrat

Michigan

Last Republican win: 1988

16 electoral votes

"I'm going to win Michigan by a lot. Republicans don't go there, horror show, closing factories there."
— Trump, 5/26/2016

Pennsylvania

Last Republican win: 1988

20 electoral votes

"I don't see how (Clinton) could do well in a place like Pennsylvania... I'm think I'm going to win Pennsylvania easily."
— Trump, 5/26/2016

Solid Democrat

California

Last Republican win: 1988

55 electoral votes

"We’re going to play heavy as an example in California... Other GOP candidates wouldn't even come here for a dinner"
— Trump, 5/26/2016

Illinois

Last Republican win: 1988

20 electoral votes

"I put so many states in play: Michigan being one. Illinois."
— Trump, 5/26/2016

New Jersey

Last Republican win: 1988

14 electoral votes

"We're going to win New Jersey."
Trump, 1/5/2016

New York

Last Republican win: 1984

29 electoral votes

"We’re going to focus on New York;" of other GOP candidates, "They wouldn’t spend 10 cents in New York."
— Trump, 5/26/2016

Oregon

Last Republican win: 1984

7 electoral votes

"Um, Oregon, nobody would even think about Oregon. I'm going to campaign there. These are states that are locks for the Democrats."
— Trump on Fox, 5/18/2016

New Mexico

Last Republican win: 2004

5 electoral votes

"I know this goes a little bit on the Democrat side but not now. Not with me. Because I'm going to bring back jobs. We're going to have a strong border. We're going to have the wall. We're going to stop drugs from coming in. We're going to have incredible trade agreements. "
— Trump, 5/24/2016

The full CNN electoral map

Source: CNN Reporting; Produced by Tal Yellin, Terence Burlij, Ben Werschkul, Jeff Simon