Eight years after he was the man try­ing to grant Barack Obama’s plea to keep his Black­Berry, Richard “Dick­ie” George is watch­ing with more than cas­u­al in­terest while an­oth­er pres­id­ent-elect fights to keep his smart­phone as a life­line out of the bubble that is the mod­ern pres­id­ency.

Obama won that battle—sort of—thanks to the work of a team at the Na­tion­al Se­cur­ity Agency headed by George, and thanks to the pres­id­ent’s will­ing­ness to ac­cept severe re­stric­tions.

Today, the chal­lenges presen­ted by Pres­id­ent-elect Don­ald Trump’s heavy use of so­cial me­dia on an un­se­cured An­droid phone are con­sid­er­ably more daunt­ing. And the out­come is less than clear only five weeks be­fore the In­aug­ur­a­tion.

Trump trans­ition of­fi­cials will not talk about the is­sue, not even re­spond­ing to ques­tions on wheth­er they have had any dis­cus­sions with the NSA. The pres­id­ent-elect, in an in­ter­view with CBS’s 60 Minutesshortly after the elec­tion, prom­ised to be “very re­strained” with Twit­ter “if I use it at all.” With 17.3 mil­lion fol­low­ers, he sees Twit­ter as “a meth­od of fight­ing back” against cri­ti­cism.

In­deed, in his postelec­tion tweets, he has at­tacked The New York Times, Van­ity Fair, CNN, NBC News, and Sat­urday Night Live. On Dec. 5, he seemed to an­swer the ques­tion about his fu­ture tweets when he tweeted: “If the press would cov­er me ac­cur­ately & hon­or­ably, I would have far less reas­on to ‘tweet.’ Sadly, I don’t know if that will ever hap­pen!”

That means the NSA, which is in charge of pro­tect­ing U.S. gov­ern­ment com­mu­nic­a­tions and in­form­a­tion sys­tems, will have to deal with a tweet-happy pres­id­ent, one who has told his aides he does not want to sur­render his Sam­sung Galaxy S4. It’s ex­actly the type of chal­lenge George thrived on dur­ing his 41 years with the NSA. Be­fore he re­tired in 2011 and be­came seni­or ad­viser for cy­ber­se­cur­ity at the Johns Hop­kins Ap­plied Phys­ics Lab, George had spent the pre­vi­ous eight years at the NSA as tech­nic­al dir­ect­or for the In­form­a­tion As­sur­ance Dir­ect­or­ate.

He was in that job on Elec­tion Day in 2008 when he was told to find a way to let Obama keep his Black­Berry. In an in­ter­view this week with Na­tion­al Journ­al, George com­pared the as­sign­ment to the NSA’s de­vel­op­ment of “Vin­son,” a se­cure voice-en­cryp­tion unit that was a fore­run­ner of the cell phone. “We de­signed that in 1957. We built the first mod­el in 1970, and we fixed everything we found wrong through the first few en­gin­eer­ing mod­els, and we fielded it in 1976. It took 19 years to get that thing out,” he said, con­trast­ing that with the three-month time frame to reen­gin­eer Obama’s phone.

To do it, he as­sembled a core team of about a dozen, with up to an­oth­er 50 work­ing on the pro­ject. In the end, after tweak­ing the phone’s al­gorithms and en­gin­eer­ing, he presen­ted the new pres­id­ent with a severely lim­ited device. Obama could call and re­ceive calls from only a hand­ful of close friends—who first had to be briefed by the White House coun­sel’s of­fice and have their devices ex­amined. He could not click on any at­tach­ments and could not tweet. “And he wasn’t play­ing Angry Birds, I can prom­ise you that,” joked George.

In Obama’s last year in of­fice, the NSA re­placed his Black­Berry with a new phone. The lim­it­a­tions re­mained in force, as the pres­id­ent joked in an ap­pear­ance on The To­night Show with Jimmy Fal­lon on June 9. Obama re­called what he was told when giv­en the new device: “This is a great phone—state of the art. But it doesn’t take pic­tures, you can’t text, the phone doesn’t work, and you can’t play your mu­sic on it,” he joked.

George was watch­ing Fal­lon that night and laughed along with the pres­id­ent. “I thought his char­ac­ter­iz­a­tion was right on. In fact, I laughed with my wife and told her, ‘Boy, did he get that right.’”

The lim­it­a­tions are crit­ic­al be­cause the threat is so dire, he said. “We are all tar­gets,” he said. “But he has got a much big­ger bull’s-eye on his back than I do or any­body else.” He ad­ded that it is al­most cer­tain that a pres­id­ent would be sent false links, of­ten dis­guised as com­ing from le­git­im­ate sources. “If someone can get in­to the sec­ret­ary of De­fense sys­tem and send a mes­sage to the pres­id­ent with a ‘You need to read this’ link, the chances are much bet­ter that he is go­ing to click on that than if it comes from some per­son he’s nev­er heard of.”

If a pres­id­ent is not care­ful, he could sur­render con­trol of his phone, his cam­era, and the device’s mi­cro­phone and GPS. “People are go­ing to try a lot harder, spend a lot more re­sources to get him. You’ve got to pro­tect your­self,” said George.

Trump’s postelec­tion tweets also have raised the pos­sib­il­ity of hack­ers send­ing out fake tweets that look as if they came from Trump and have the po­ten­tial of af­fect­ing the stock mar­ket or trig­ger­ing for­eign crises. Two com­pan­ies already saw their val­ues drop fol­low­ing barbed early-morn­ing tweets from Trump. On Dec. 6, he cri­ti­cized the amount he said—in­ac­cur­ately—Boe­ing was spend­ing on a new Air Force One, de­mand­ing, “Can­cel or­der!” Boe­ing’s shares lost al­most 1 per­cent at the open­ing of trad­ing on the New York Stock Ex­change. Six days later, Lock­heed Mar­tin suffered a more than 5 per­cent hit after Trump tweeted that the cost of the F-35 fight­er jet pro­gram was “out of con­trol.”

“And,” said George, “those were really mild things he said. You could really tank a com­pany if you wanted to” with a fake tweet. “The im­pact he can have is phe­nom­en­al.”

For Trump, George sus­pects the an­swer will be giv­ing him mul­tiple devices. “It’s not like he is only go­ing to have one device to do things from. And it’s not like he has to worry about car­ry­ing ex­tra devices. There are people who will be car­ry­ing stuff for him.” George said the func­tion­al­ity of one device can be lim­ited to send­ing tweets. “This is the device that you only Twit­ter on. You don’t take phone calls, you don’t send emails. You Twit­ter on this and nobody is call­ing you on this.” An­oth­er phone would be used for calls to his fam­ily.

NSA of­fi­cials know, though, that no pres­id­ent has to listen to them. They can only hope that Trump is as co­oper­at­ive as Obama was. “He is the pres­id­ent; he gets to make the risk-man­age­ment de­cision,” said George. “The good news was that Obama was about as easy to work with as you could ima­gine. He didn’t fight us at any step. He took it really ser­i­ously, and what more could you ask for?”

With Trump, he said, “We can sug­gest. But no one is go­ing to tell him.” He ad­ded, “This is the pres­id­ent. He can do what he wants. But pres­id­ents are in­her­ently really smart people. They un­der­stand the risks that they take and they try to play the game right. You don’t get to be pres­id­ent if you don’t un­der­stand that kind of stuff.”