OCTOBER SURPRISE: Iran’s new MIDDLE EAST plan to ‘mess with Trump’

>> Aishah: KYIV IS REELING AFTER. AN INTENSE MISSILE AND DRONE. ATTACK BY RUSSIA. THE STRIKES STARTED JUST HOURS. AFTER RUSSIAN PRESIDENT PUTIN. AGREED IN PRINCIPLE TO RESUME A. THREE-WAY CONVERSATION EARLIER. THIS WEEK. PRESIDENT TRUMP ASKED ABOUT IT. JUST YESTERDAY. LISTEN. >> ON UKRAINE, PRESIDENT. ZELENSKYY SAID THE NEW RUSSIA. STRIKES OVERNIGHT ARE PROOF.

NOTHING HAS CHANGED WITH PUTIN. HE DOESN'T WANT PEACE. >> President Trump: WE'LL SEE. HOW IT WORKS OUT. IT HAS BEEN HAPPENING A LOT. >> Aishah: THE FORMER SENIOR. DIRECTOR IN THE BUSH NFC AND. STAFF DIRECTOR OF THE HOUSE. INTEL COMMITTEE. MICHAEL JOINS US LIVE NOW. WHAT IS YOUR TAKE? ZELENSKYY IS SAYING THIS IS MORE. OF THE SAME. >> I THINK PUTIN WILL CONTINUE. TO PUT THE PRESSURE ON EVEN IF. WE'RE ON THE VERGE OF PEACE. TALKS. HE IS LOSING ON THE BATTLEFIELD.

AND HIS STRATEGY IS TO POUND. KYIV WITH BALLISTIC MISSILES AND. DRONES ESPECIALLY OVER THE. BITTERLY COLD UKRAINE WINTER TO. TRY TO GET THEM OR CONDITION THE. UKRAINIANS TO WANT TO COME TO. THE TABLE TO MAKE CONCESSIONS. I DON'T THINK IT WILL WORK. THE UKRAINIANS ARE TOUGH AS. NAILS BUT I THINK THAT'S PUTIN'S. PLAN. >> Bill: THIS WAR HAS BEEN GOING. ON LONGER THAN WORLD WAR I. NOT A LOT IS CHANGING PHYSICALLY. ON THE GROUND. BOTH SIDES DUG IN POUNDING EACH. OTHER WITH DRONES AND MISSILES. IF PUTIN DOESN'T WANT TO MAKE A.

DEAL REALISTICALLY HOW DO THEY. EVER GET OUT OF THIS QUAGMIRE. >> THEY WOULD HAVE TO DECLARE. THE SPACE THEY'RE AT NOW A. DEMILITARIZED ZONE IN THE. MIDDLE. THE UKRAINIANS CAN'T GIVE UP. ANYMORE TERRITORY. THEY HAVE -- IF THEY LET THE. RUSSIANS COME OVER IT WOULD BE. SMOOTH COULD YOU PASTURES TO. KYIV. THEY FEEL THEY NEED TO STAY. WHERE THEY ARE. LET'S KEEP THE LINES WHERE THEY.

ARE. THE PRESIDENT IS ON TO THIS. DEMILITARIZED ZONE OR SOMETHING. IN THE MIDDLE AND TRY TO WALK. BACK THE TENSIONS OVER MANY, MANY MONTHS. I THINK THAT'S WHERE THEY WILL. GO EVENTUALLY IF PUTIN AND KYIV. WANT TO DO IT. >> Aishah: SOUNDS LIKE THEY WILL. HAVE THE MEETINGS AFTER THE. MID-TERMS. PROBABLY A WEEK AFTER THE. MID-TERMS. THE TWO SIDES ARE PRETTY FAR. APART, RIGHT? >> VERY. AT A MINIMUM UKRAINIANS WILL. HAVE TO ACKNOWLEDGE THAT EVER.

PIECE OF LAND THEY HAVE LOST ON. THE BATTLEFIELD IS DEFACT OWE. RUSSIA'S. UKRAINE'S LINE IS AND IN THEIR. CONSTITUTION THAT THEY JUST. CAN'T GIVE UP LAND FOR FREE TO. THE RUSSIANS. I THINK THAT'S WHAT PUTIN WANTS. PUTIN WOULD HAVE TO WALK BACK. SOME OF THESE DESIRES TO HAVE. THE ENTIRETY OF THE DONBAS. BECAUSE OF THIS FORTRESS BUILT. AND IN HIS INTEREST TO REBUILD.

HIS ECONOMY. MAYBE HIS MILITARY, TOO AND. UKRAINE THE SAME. I THINK WE TRY TO GET THE DO TO. SAY WE'RE AT THE POINT OF. EXHAUSTION AND --. >> Bill: WANT TO ASK YOU ABOUT. THE WAR IN IRAN. MULTIPLE REPORTS COMING OUT THE. U.S. AND ISRAEL ARE PRESSING TO. HIT IRAN BUT NOT BEFORE THE. MID-TERMS. IRAN IS RESPONDING TO THAT IN. THE "WALL STREET JOURNAL" THEY. WRITE QUOTE IRAN THREATENS WIDER. STRIKES ON ECONOMIC AND CIVILIAN. TARGETS IN U.S. ATTACKS.

IN PRIVATE DIPLOMATIC. COMMUNICATIONS ARE AIMED AT. DETERRING ANY ATTACK WITH TOUGH. TALK BUT SIGNAL A REAL THREAT. IRAN RETAINS SIGNIFICANT MISSILE. AND DRONE STOCKS AND THE ABILITY. TO USE THEM. WHAT IS YOUR BIRD'S EYE VIEW. >> THE REASON THE ISRAELIS AND. UNITED STATES ARE THINKING ABOUT. GOING BACK TO WAR IS TO. COMPLEMENT THE STRANGULATION. THAT WE HAVE ON THEM. ECONOMICALLY. I THINK THEY ARE CONSIDERING HOW. MUCH MORE CAN WE INCREASE THE. PRESSURE TO GET A GOOD.

DIPLOMATIC ARRANGEMENT. IF THE PRESIDENT FEELS LIKE IN. ADDITION TO DEGRADING THEIR. MISSILE CAPABILITY, WHICH IS. VERY IMPORTANT, THAT HE ALSO. WANTS TO HIT SOME IRANIAN ENERGY. TARGETS, IT WOULD BE AGAIN TO. CONDITION THEM TO COME TO THE. TABLE AND MAKE SOME ARRAIGNMENT. WITH US. IF I'M THE PRESIDENT I WANT TO. KNOW WHY I'M GOING TO WAR BEFORE. I DO IT. THE ECONOMIC BLOCKADE IS WORKING. WELL RIGHT NOW. IT'S EXPLAINABLE AND SUSTAINABLE.

AND OIL HAS GONE BACK TO PRE-WAR. LEVELS. THE WALL STREET YOUR ALL REPORT. EVIDENCE THAT THIS WEEK. WE HAVE TO GET PAST THE. ELECTION. I DON'T THINK THE IRANIANS WILL. GIVE US ANYTHING. >> Aishah: I KEEP HEARING THAT. THERE WILL BE AN OCTOBER. SURPRISE AND IRAN WILL DO. SOMETHING IN THE MIDDLE EAST. RIGHT BEFORE THE ELECTIONS TO. MESS WITH PRESIDENT TRUMP'S. CHANCES. >> I THINK YOU'RE RIGHT. THEY ARE FORECASTING THE. REPUBLICANS MIGHT LOSE THE HOUSE.

OF REPRESENTATIVES AND I THINK. THEY WANT TO -- I DO.