This Man Is the Future of Super PACs

Multimillionaire John Jordan is one of a growing number of donors taking matters into their own hands.

Lights, camera, super PAC action: Jordan
National Journal
Shane Goldmacher
See more stories about...
Shane Goldmacher
May 5, 2014, 1 a.m.

HEALDS­BURG, Cal­if. — It’s a Monday af­ter­noon in mid-March, and Re­pub­lic­an mul­ti­mil­lion­aire John Jordan is pre­par­ing to host House Speak­er John Boehner for din­ner the fol­low­ing Sat­urday — not that he sounds par­tic­u­larly ex­cited about it. “I know that, tra­di­tion­ally, that it makes donors feel good that the can­did­ates, the politi­cians come,” he tells me, as he steps in­to the in­tim­ate din­ing room where they’ll be eat­ing. “I really don’t care.”

Jordan isn’t fuss­ing much over the menu, oth­er than to en­sure that there will be gen­er­ous amounts of the ac­claimed caber­net sauvign­on pro­duced on his 1,450-acre North­ern Cali­for­nia vine­yard. (Boehner’s love of reds is widely known.) He does have one sur­prise in mind: a 9-foot mech­an­ized di­no­saur that will ap­pear, part­way through the meal, amid the gi­ant wine tanks that the din­ing room over­looks. Jordan wants the event — where he and oth­er donors will mingle with Boehner and se­lect staff — to be any­thing but bor­ing. Along those lines, he has one rule for his polit­ic­al guests: no speeches. “We all know what they’re go­ing to say any­way,” he ex­plains.

This is Boehner’s second vis­it to the vine­yard in as many years. The last time the speak­er swung through town, in March 2013, Jordan — who took over the wine busi­ness from his par­ents — dashed off more than $80,000 in checks to his guest and vari­ous oth­er GOP groups. In­deed, ac­cord­ing to the Cen­ter for Re­spons­ive Polit­ics, last year he was the third-largest in­di­vidu­al su­per PAC con­trib­ut­or in the na­tion, be­hind only bil­lion­aires Mi­chael Bloomberg and Tom Stey­er. No won­der so many prom­in­ent Re­pub­lic­ans — the list in­cludes Mitch Mc­Con­nell, Rick Perry, and Tim Pawlenty — have made the trek to Jordan’s winery in re­cent years.

Still, Jordan in­sists he doesn’t like glad-hand­ing with politi­cians. “I’m not try­ing to spoon with them,” he says. “I don’t care. In fact, I try to avoid — I go out of my way to avoid meet­ing can­did­ates and politi­cians.” Why? “All too of­ten, these people are so dis­ap­point­ing that it’s de­press­ing. Most of these people you meet, they’re un­em­ploy­able.”¦ It’s just easi­er not to know.”

“I go out of my way to avoid meet­ing can­did­ates and politi­cians. All too of­ten, these people are so dis­ap­point­ing that it’s de­press­ing.”

What Jordan — 42 years old this month, with sandy blond hair and a line­back­er’s build — loves is not the politi­cians them­selves but the game of polit­ics. He reads the Drudge Re­port, Real­Clear­Polit­ics, and the D.C. polit­ic­al rags re­li­giously. He con­sumes polling crosstabs and stud­ies the latest ads in races across the coun­try. He spends about three hours a day feed­ing his polit­ic­al ap­pet­ite. “I geek out on this stuff,” he says.

In 2012, Jordan donated to the Karl Rove”“af­fil­i­ated Cross­roads net­work. But his geeki­est and pri­ci­est polit­ic­al mo­ment came last June, when he cre­ated his own su­per PAC, hired his own cam­paign team, and poured more than $1.4 mil­lion of his own money in­to a single can­did­ate — Re­pub­lic­an Gab­ri­el Gomez, who was con­test­ing a spe­cial elec­tion 3,000 miles away to fill John Kerry’s Sen­ate seat in Mas­sachu­setts — des­pite the fact that Jordan had nev­er met or spoken to him. Gomez lost the elec­tion, but Jordan con­tin­ues to plan for­ays in­to the polit­ic­al world. This week, he fun­ded a flight of ads in Ore­gon’s con­tested Re­pub­lic­an Sen­ate primary, and he is con­tem­plat­ing more such in­ter­ven­tions in the near fu­ture.

For Jordan, build­ing his own highly spe­cif­ic polit­ic­al or­gan­iz­a­tions is prov­ing much more at­tract­ive than simply dol­ing out checks to om­ni­bus groups like Cross­roads. And he’s one of a grow­ing num­ber of mil­lion­aires and bil­lion­aires who are tak­ing this ap­proach. The biggest of these do-it-your­self donors — people such as Bloomberg or broth­ers Charles and Dav­id Koch — are house­hold names. But a num­ber of re­l­at­ively an­onym­ous free-spend­ers are also opt­ing to play the role of king­maker on their own terms. This group in­cludes hedge-fund man­ager Sean Fieler, who has al­most single-handedly bank­rolled a su­per PAC that aims to elect so­cial con­ser­vat­ives; Miami re­tir­ee Ron­ald Fir­man, who re­cently poured $1.5 mil­lion in­to an un­suc­cess­ful su­per PAC cam­paign in a Flor­ida House spe­cial elec­tion; and Jonath­an Sor­os, the son of lib­er­al fin­an­ci­er George Sor­os, who has a su­per PAC ded­ic­ated to, of all things, lessen­ing the im­pact of big money in polit­ics.

In oth­er words, Amer­ic­an polit­ics is about to have many more John Jord­ans. There’s go­ing to be a su­per PAC on nearly every corner, many of them fun­ded by people you’ve nev­er heard of. “The su­per PAC world is go­ing to be a lot more balkan­ized,” Jordan says. “There’s not go­ing be one big su­per PAC. It’s not go­ing to be like it was in 2012 ever again.”

DIS­IL­LU­SION­MENT

Jordan is a proud Re­pub­lic­an, though he doesn’t like to be con­fined to an ideo­lo­gic­al cubby. He sup­ports abor­tion rights and gay mar­riage, and his winery hawks its com­mit­ment to sol­ar power. But he’s deeply wor­ried about the grow­ing size and in­trus­ive­ness of gov­ern­ment. “It is truly about the in­di­vidu­al versus the state and the growth of the state,” he says of the Obama era.

The winery own­er first met Karl Rove at Fox News stu­di­os in New York City more than two years ago, back when he was dat­ing one of the chan­nel’s cor­res­pond­ents, Ju­liet Huddy. Jordan and his par­ents had been long­time Re­pub­lic­an donors, but when he saw Rove, he told him he was think­ing of get­ting quite a bit more in­volved. At the time, Rove was build­ing a jug­ger­naut at Amer­ic­an Cross­roads and Cross­roads GPS, the su­per PAC and non­profit that to­geth­er amoun­ted to the biggest pro-Re­pub­lic­an polit­ic­al ap­par­at­us in the coun­try. Karl Rove (Tom Pen­ning­ton/Getty Im­ages)

It was Rove’s task to help reel in big-fish con­trib­ut­ors, and Jordan had hooked him­self on the line. So it wasn’t long be­fore Rove was wind­ing past the gates of Jordan’s Healds­burg es­tate and up the scen­ic mile-long drive­way for an in­tim­ate din­ner to make his pitch. Jordan and Rove sub­sequently at­ten­ded the Ken­tucky Derby to­geth­er, along with Rove’s then-fiancée, Kar­en John­son, and Huddy. (Huddy and Jordan have since split.)

Jordan says he soon be­came a “sev­en-fig­ure con­trib­ut­or and raiser” to Cross­roads, but even be­fore the dis­ap­point­ment of Novem­ber 2012, he found him­self frus­trated. Jordan had thought his hefty check would grant him a priv­ileged po­s­i­tion in­side one of the na­tion’s biggest Re­pub­lic­an op­er­a­tions. In­stead, he felt like he was on the out­side look­ing in. “With Cross­roads all you got was, Karl Rove would come and do his little rain dance,” Jordan says. He didn’t com­plain aloud so much as stew. “You write them the check and they have their in­vestors’ con­fer­ence calls, which are” — Jordan pauses here for a full five seconds, be­fore de­cid­ing what to say next — “something else. You learn noth­ing. They ex­plain noth­ing. They don’t dis­close any­thing even to their big donors.” (Cross­roads Com­mu­nic­a­tions Dir­ect­or Paul Lind­say re­spon­ded via email, “We ap­pre­ci­ated Mr. Jordan’s sup­port in 2012 and his fre­quent in­put since then.” Rove de­clined to com­ment.)

The Cross­roads net­work raised a com­bined $325 mil­lion in the 2012 elec­tion cycle. Yet Mitt Rom­ney lost. So did Scott Brown, Rick Berg, and George Al­len. Al­most every Re­pub­lic­an in every Sen­ate race in the coun­try that Cross­roads spent money on lost, with the ex­cep­tion of Dean Heller in Nevada. To Jordan, Cross­roads’ strategy was just “spray-and-pray ad­vert­ising.” Worse, Jordan had no idea where all his money had gone. It turns out that the se­cret­ive nature of the non­profit Cross­roads GPS and some opaque dis­clos­ure laws kept even its biggest donors in the dark about the de­tails. Jordan wanted to know who had scored com­mis­sions on ad buys, what was spent on tele­vi­sion versus on­line, and, at the most ba­sic level, “who’s mak­ing what.” He couldn’t find out. “To hell with this,” he de­cided.

BLURRED VINES

Jordan sips soda from a plastic Den­ver Bron­cos cup as we tour the winery grounds his par­ents pur­chased on the same day, in 1972, that he was born. Today, the prop­erty has a small grass land­ing strip and an air­plane hangar where Jordan stows the smal­lest of his three planes, a yel­low Piper Cub. He flies three or four times a week “even just to bore a hole in the sky.” He in­sists on man­ning the con­trols, even if he’s cross­ing the con­tin­ent in his G3 jet. “I like air­planes flown by me,” he says.

Some of Jordan’s prop­erty can be seen in the vari­ous videos pro­duced by the winery’s staff video­graph­er. They are mostly stand­ard fare — chardon­nay this, som­meli­er that. But a few stand out, such as a 2013 par­ody mu­sic video of Robin Thicke’s Blurred Lines. The plot­line of Blurred Vines, per the winery: “In the world of wine, there are two types of men: wine geeks and wine dudes. Geeks ob­sess over wine lists, wine scores, and wine­mak­ing tech­niques. Dudes love their wine but don’t take it too ser­i­ously. Who gets the girl?”

{{third­PartyEmbed type:you­tube id:19T90ut2JEE}}

Spoil­er alert: Jordan does. In shades, a blazer, and an open-col­lar white shirt, Jordan shakes a mag­num of caber­net at bux­om wo­men who shimmy in skin­tight dresses. One of them pro­voc­at­ively feeds him grapes. An­oth­er lights his ci­gar as she licks her lip­stick-reddened lips. The wo­men end up stripped down to bikinis in his hot tub.

The four-minute You­Tube video has been viewed about 35,000 times. “This is like something Mi­chael Scott would do,” wrote one on­line com­menter, re­fer­ring to the glee­fully ig­nor­ant boss on The Of­fice.

Jordan loves the videos. An­oth­er fea­tured him and his staffers dan­cing Gang­nam-style. An ex-cheer­lead­er on staff did the cho­reo­graphy. “We had prac­tice,” he says. “Sev­er­al prac­tices.” As for the scantily clad wo­men in Blurred Vines, he says they were vo­lun­teers. “Look, the wine busi­ness, at the end of the day, too many people take too ser­i­ously,” Jordan says. “If you can’t have fun around wine, it’s a you prob­lem.”

Life is fun when you’re mak­ing money. Jordan has been run­ning the winery’s day-to-day op­er­a­tions since 2005 — after a wind­ing early ca­reer that in­cluded the Nav­al Re­serve, busi­ness school, law school, and start­ing his own law prac­tice. Jordan Vine­yard & Winery ships out more than 100,000 cases of wine each year, he says, and Wine and Spir­its re­cently named Jordan the second-most-pop­u­lar brand in the coun­try among the na­tion’s top res­taur­ants, even with its av­er­age res­taur­ant price of more than $100 per bottle. The wine has been a hit for a gen­er­a­tion; the Re­agan White House served it at the 1987 state din­ner for So­viet lead­er Mikhail Gorbachev.

The wine busi­ness alone isn’t fuel­ing Jordan’s polit­ic­al giv­ing, though. He says he made some tech­no­logy-stock bets in re­cent years that paid off big (he de­clined to say which com­pan­ies). He has also cofoun­ded a tech com­pany of his own, which makes an iPad app for res­taur­ants.

CLOAKED IN SECRECY

After the 2012 elec­tion, Jordan was flush, frus­trated, and look­ing for some­where “fun” to spend his money. He found his op­por­tun­ity when John Kerry va­cated his Sen­ate seat to be­come sec­ret­ary of State. Re­pub­lic­ans re­cruited Gab­ri­el Gomez — a hand­some 47-year-old former Navy SEAL who sup­por­ted im­mig­ra­tion re­form, ex­pan­ded back­ground checks for gun buy­ers, and gay mar­riage — to run in a spe­cial elec­tion for the seat. Gab­ri­el Gomez (Jes­sica Rinaldi For The Bo­ston Globe)

Gomez was ex­actly the kind of out-of-the-box can­did­ate the GOP’s eld­er states­men had been de­mand­ing in the wake of the 2012 de­feats. Yet weeks away from the June spe­cial elec­tion, it was only Demo­crat­ic groups that had in­ves­ted in the race, back­ing vet­er­an Demo­crat­ic Rep. Ed­ward Mar­key to the tune of mil­lions. The U.S. Cham­ber of Com­merce, the Koch broth­ers’ net­work, and Cross­roads all sat on the side­lines. “There was a lot more in­terest in na­vel-gaz­ing and pout­ing about 2012,” says Brad Todd, one of Gomez’s ad­visers, who pleaded pub­licly for help. “Our donor base was guilty of not be­ing will­ing to take its as­pir­in and get over its hangover.”

But Jordan was watch­ing closely. In early June, he asked Re­pub­lic­an poll­ster John McLaugh­lin to sur­vey the con­test for him. The two had teamed up a few months earli­er, along with con­ser­vat­ive act­iv­ist Dick Mor­ris, on a poll of His­pan­ic-Amer­ic­ans about im­mig­ra­tion. On June 4, McLaugh­lin went in­to the field, on Jordan’s dime, and came back with the res­ults the next day: Mar­key, 45 per­cent; Gomez, 44 per­cent. “It was win­nable,” McLaugh­lin says. Pa­per­work was filed that day, and a su­per PAC was born. “It was a res­cue mis­sion on the fly,” Jordan says. “Four days be­fore, five days be­fore go­ing on the air, I had no idea I was even go­ing to do it.”

Jordan quickly as­sembled a polit­ic­al team. McLaugh­lin would serve as poll­ster. Sheena Tahilramani, Rove’s former chief of staff, would be his spokes­wo­man. Rick Wilson, a Flor­ida-based strategist, would cut the ads. Cleta Mitchell, a prom­in­ent GOP law­yer, would handle leg­al mat­ters. The group was giv­en a de­cept­ively non-Re­pub­lic­an name: Amer­ic­ans for Pro­gress­ive Ac­tion.

The date on the su­per PAC fil­ing was key. Be­cause it came less than three weeks be­fore Elec­tion Day, Jordan wouldn’t have to be re­vealed as its fun­der un­til after the elec­tion. Jordan in­sists this was a “co­in­cid­ence.” “I’m not say­ing I was dis­ap­poin­ted by it. And I’m not say­ing I wouldn’t do it that way,” he says now. “But in this case, it truly wasn’t [in­ten­tion­al].” As for the Demo­crat­ic-sound­ing name, he says, “Cleta Mitchell says you’ve got to have a name. I’m like, ‘Oh, shit, I’ve got to think of a name.’ “¦ I thought of that in the shower.”

Late-night con­fer­ence calls were sched­uled to go over the latest polling and stat­ist­ics from the field. “We would be on the phone, mid­night East Coast time, go­ing through the data,” McLaugh­lin says, “what was good, what was bad.” Des­pite a blitz of Jordan-fun­ded ads, the polls soon took a turn for the worse. Demo­crats were on the air, too, and the party faith­ful were co­ales­cing be­hind their nom­in­ee. Mar­key had widened his lead by June 19, ac­cord­ing to in­tern­al-polling res­ults provided by McLaugh­lin. They can­celed a fi­nal series of ads the week­end be­fore the race, and Jordan re­fun­ded him­self $273,000.

All the while, Jordan’s role re­mained cloaked in secrecy. As the ads filled the Mas­sachu­setts air­waves, the mys­tery of who was be­hind them grew. There was little to go on — just the name of Nancy Watkins, the GOP treas­urer who had signed the pa­per­work, and Tahilramani, the spokes­wo­man. Fi­nally, on June 21, four days be­fore the elec­tion and two days after the poll that caused them to pull the plug, Jordan outed him­self to The Wall Street Journ­al as the sole con­trib­ut­or. “Here I saw an Amer­ic­an hero run­ning in a close race in a tough state while get­ting ab­so­lutely poun­ded by Demo­crats throw­ing everything they could at him,” Jordan told the pa­per. “I just couldn’t sit by and watch and leave him alone while the es­tab­lish­ment Re­pub­lic­an groups de­cided to sit on their hands and just leave him on the beach.” Jordan gave me much the same ra­tionale: “It’s a Navy thing, first of all,” he said. “That’s hard to ex­plain.”

Jordan had blown through more than $1.4 mil­lion in two weeks on a los­ing ef­fort — and he loved every second of it. “I nev­er had any il­lu­sions about the prob­ab­il­ity of suc­cess. At the same time, some­body has to try, and you nev­er know. You lose 100 per­cent of the shots you don’t take, so why not do it?” he says. “And I’ve al­ways thought it would be fun to do, and I had a great time do­ing it, frankly.” Now, Jordan says that the Gomez race was just the be­gin­ning — a $1.4 mil­lion “po­ten­tial ice­berg tip” of fu­ture polit­ic­al ef­forts.

THE SPLIN­TER­ING OF SU­PER PACS

At the same time Jordan was help­ing Gomez, Tom Stey­er was tap­ping his per­son­al for­tune to de­feat him. The Cali­for­nia-based re­tired hedge-fund in­vestor had cre­ated a su­per PAC of his own, Nex­t­Gen Cli­mate Ac­tion, to elect can­did­ates who prom­ised to ad­dress cli­mate change. Stey­er spent mil­lions in 2013, in­clud­ing in the Mas­sachu­setts Sen­ate race and the Vir­gin­ia gov­ernor’s race. He is now plot­ting a re­por­ted $100 mil­lion push in the 2014 elec­tions — half from him, half from oth­er like-minded donors.

“If you’re a busi­ness lead­er who wants to make a dif­fer­ence on policy is­sues, it may make sense to start your own or­gan­iz­a­tion.”

Every­where you look these days, wealthy donors are, like Jordan, tak­ing a DIY ap­proach to their polit­ic­al act­iv­ism. Bloomberg has star­ted his own an­ti­gun group. Mark Zuck­er­berg and oth­er tech elites wanted im­mig­ra­tion re­form, so they launched their own ad­vocacy arm. Joe Rick­etts, the founder of TD Amer­it­rade, es­tab­lished End­ing Spend­ing, a su­per PAC and a non­profit that seek to rein in the fed­er­al debt. “If you’re a busi­ness lead­er who wants to make a dif­fer­ence on policy is­sues, it may make sense to start your own or­gan­iz­a­tion,” says Bri­an Baker, pres­id­ent of the End­ing Spend­ing en­tit­ies and a polit­ic­al ad­viser to Rick­etts. “That is the clas­sic hall­mark of an en­tre­pren­eur.”

The world of the polit­ic­ally act­ive su­per­rich is small. They tend to con­greg­ate and com­mu­nic­ate to­geth­er. Bil­lion­aire hedge-fund in­vestor Paul Sing­er, for in­stance, is a be­ne­fact­or of End­ing Spend­ing ($350,000 in March 2014) and Amer­ic­an Cross­roads ($250,000, again in March 2014). But he has also seeded a su­per PAC of his own, the Amer­ic­an Unity PAC, ded­ic­ated to elect­ing pro-gay-rights Re­pub­lic­ans.

One com­mon­al­ity among these men of means (and it’s al­most all men) is their pas­sion for polit­ics. They want to do more than donate; they want to shape events. “More and more you can find that, as a com­mit­ted, in­formed in­di­vidu­al donor, you can as­semble the right kind of tools to be ef­fect­ive and move num­bers in cam­paigns,” says Wilson, the GOP con­sult­ant who de­signed Jordan’s pro-Gomez ads. And un­sur­pris­ingly, the su­per-wealthy tend to be­lieve they are rich for a reas­on: their smarts. “If you read enough, like what goes on in cam­paigns, and you read all the trade journ­als, it isn’t very hard,” Jordan says. “It’s not brain sur­gery.”

Go­ing it alone has po­ten­tial draw­backs, of course. Rich busi­ness­men are, al­most by defin­i­tion, polit­ic­al novices. They are at risk of sad­dling up to a con­sult­ant who can take them to the clean­ers, or mis­judging the im­pact their money can have in a par­tic­u­lar race. In­deed, some es­tab­lish­ment GOP op­er­at­ives have scoffed at Jordan’s Gomez in­vest­ment as fool­hardy. Mar­key, they point out, won by a com­fort­able 10 per­cent­age points.

Still, the fur­ther splin­ter­ing of the su­per PAC uni­verse now seems in­ev­it­able. And it rep­res­ents a chal­lenge to the re­l­at­ive power of polit­ic­al parties and large out­lets that, like Cross­roads, are not donor-led. For ex­ample, the Kochs, lead­ers of one of the ori­gin­al do-it-your­self donor ef­forts, have lapped Cross­roads so far in the 2014 Sen­ate races. The Koch-linked Amer­ic­ans for Prosper­ity and Free­dom Part­ners had spent a com­bined $23.5 mil­lion on ads in Sen­ate races as of late April, com­pared with $2.6 mil­lion for Cross­roads, ac­cord­ing to a Demo­crat­ic source track­ing ad buys. (The Cross­roads su­per PAC’s fun­drais­ing did pick up dra­mat­ic­ally in March, post­ing its best month since the 2012 elec­tions.)

Just this week, Jordan launched his latest ven­ture, fund­ing ads in Ore­gon’s May 20 GOP primary on be­half of Mon­ica We­hby, a pe­di­at­ric neurosur­geon. Jordan sees her as “a sleep­er” can­did­ate against Demo­crat­ic Sen. Jeff Merkley, es­pe­cially giv­en the state’s dis­astrously or­gan­ized Obama­care ex­change. “The nat­ur­al at­mo­spher­ics are right,” he says. Jordan has giv­en his money through Ne­wRe­pub­lic­an.org, a su­per PAC or­gan­ized last year by GOP op­er­at­ive Alex Cas­tel­lanos; the wealthy De­Vos fam­ily is the oth­er main con­trib­ut­or. As he was in the Mas­sachu­setts elec­tion, Jordan is heav­ily in­volved in the su­per PAC’s strategy. “It will be hard for any­body to get a big check out of me to a su­per PAC that I’m not in the middle of,” Jordan says. “Mostly, be­cause I don’t trust them.” (He did say he might carve out an ex­cep­tion for the Kochs.)

Jordan doesn’t have a horse yet in the 2016 pres­id­en­tial race, but Sen. Rand Paul of Ken­tucky in­trigues him. “I ad­mire what he is do­ing in terms of broad­en­ing the party’s ap­peal,” Jordan says. In mid-March, he had men­tioned New Mex­ico Gov. Susanna Mar­tinez to me as an­oth­er in­triguing fig­ure; sure enough, by late April, she had come to his chat­eau for a fun­draiser and stayed the night in one of his guest cot­tages. She was a bright ex­cep­tion, he says, to his gen­er­al rule that pols are an “over­dose of un­der­whelm.”

Whatever’s next, Jordan is sure to be in the cock­pit, as he is in his planes. “If you have the abil­ity to do it, why not do it?” he says. “Polit­ic­al cam­paigns are so much fun.”

DISILLUSIONMENT

Jordan is a proud Re­pub­lic­an, though he doesn’t like to be con­fined to an ideo­lo­gic­al cubby. He sup­ports abor­tion rights and gay mar­riage, and his winery hawks its com­mit­ment to sol­ar power. But he’s deeply wor­ried about the grow­ing size and in­trus­ive­ness of gov­ern­ment. “It is truly about the in­di­vidu­al versus the state and the growth of the state,” he says of the Obama era.

The winery own­er first met Karl Rove at Fox News stu­di­os in New York City more than two years ago, back when he was dat­ing one of the chan­nel’s cor­res­pond­ents, Ju­liet Huddy. Jordan and his par­ents had been long­time Re­pub­lic­an donors, but when he saw Rove, he told him he was think­ing of get­ting quite a bit more in­volved. At the time, Rove was build­ing a jug­ger­naut at Amer­ic­an Cross­roads and Cross­roads GPS, the su­per PAC and non­profit that to­geth­er amoun­ted to the biggest pro-Re­pub­lic­an polit­ic­al ap­par­at­us in the coun­try. Karl Rove (Tom Pen­ning­ton/Getty Im­ages)

It was Rove’s task to help reel in big-fish con­trib­ut­ors, and Jordan had hooked him­self on the line. So it wasn’t long be­fore Rove was wind­ing past the gates of Jordan’s Healds­burg es­tate and up the scen­ic mile-long drive­way for an in­tim­ate din­ner to make his pitch. Jordan and Rove sub­sequently at­ten­ded the Ken­tucky Derby to­geth­er, along with Rove’s then-fiancée, Kar­en John­son, and Huddy. (Huddy and Jordan have since split.)

Jordan says he soon be­came a “sev­en-fig­ure con­trib­ut­or and raiser” to Cross­roads, but even be­fore the dis­ap­point­ment of Novem­ber 2012, he found him­self frus­trated. Jordan had thought his hefty check would grant him a priv­ileged po­s­i­tion in­side one of the na­tion’s biggest Re­pub­lic­an op­er­a­tions. In­stead, he felt like he was on the out­side look­ing in. “With Cross­roads all you got was, Karl Rove would come and do his little rain dance,” Jordan says. He didn’t com­plain aloud so much as stew. “You write them the check and they have their in­vestors’ con­fer­ence calls, which are” — Jordan pauses here for a full five seconds, be­fore de­cid­ing what to say next — “something else. You learn noth­ing. They ex­plain noth­ing. They don’t dis­close any­thing even to their big donors.” (Cross­roads Com­mu­nic­a­tions Dir­ect­or Paul Lind­say re­spon­ded via email, “We ap­pre­ci­ated Mr. Jordan’s sup­port in 2012 and his fre­quent in­put since then.” Rove de­clined to com­ment.)

The Cross­roads net­work raised a com­bined $325 mil­lion in the 2012 elec­tion cycle. Yet Mitt Rom­ney lost. So did Scott Brown, Rick Berg, and George Al­len. Al­most every Re­pub­lic­an in every Sen­ate race in the coun­try that Cross­roads spent money on lost, with the ex­cep­tion of Dean Heller in Nevada. To Jordan, Cross­roads’ strategy was just “spray-and-pray ad­vert­ising.” Worse, Jordan had no idea where all his money had gone. It turns out that the se­cret­ive nature of the non­profit Cross­roads GPS and some opaque dis­clos­ure laws kept even its biggest donors in the dark about the de­tails. Jordan wanted to know who had scored com­mis­sions on ad buys, what was spent on tele­vi­sion versus on­line, and, at the most ba­sic level, “who’s mak­ing what.” He couldn’t find out. “To hell with this,” he de­cided.

<em>BLURRED VINES</em>

Jordan sips soda from a plastic Den­ver Bron­cos cup as we tour the winery grounds his par­ents pur­chased on the same day, in 1972, that he was born. Today, the prop­erty has a small grass land­ing strip and an air­plane hangar where Jordan stows the smal­lest of his three planes, a yel­low Piper Cub. He flies three or four times a week “even just to bore a hole in the sky.” He in­sists on man­ning the con­trols, even if he’s cross­ing the con­tin­ent in his G3 jet. “I like air­planes flown by me,” he says.

Some of Jordan’s prop­erty can be seen in the vari­ous videos pro­duced by the winery’s staff video­graph­er. They are mostly stand­ard fare — chardon­nay this, som­meli­er that. But a few stand out, such as a 2013 par­ody mu­sic video of Robin Thicke’s Blurred Lines. The plot­line of Blurred Vines, per the winery: “In the world of wine, there are two types of men: wine geeks and wine dudes. Geeks ob­sess over wine lists, wine scores, and wine­mak­ing tech­niques. Dudes love their wine but don’t take it too ser­i­ously. Who gets the girl?”

{{third­PartyEmbed type:you­tube id:19T90ut2JEE}}

Spoil­er alert: Jordan does. In shades, a blazer, and an open-col­lar white shirt, Jordan shakes a mag­num of caber­net at bux­om wo­men who shimmy in skin­tight dresses. One of them pro­voc­at­ively feeds him grapes. An­oth­er lights his ci­gar as she licks her lip­stick-reddened lips. The wo­men end up stripped down to bikinis in his hot tub.

The four-minute You­Tube video has been viewed about 35,000 times. “This is like something Mi­chael Scott would do,” wrote one on­line com­menter, re­fer­ring to the glee­fully ig­nor­ant boss on The Of­fice.

Jordan loves the videos. An­oth­er fea­tured him and his staffers dan­cing Gang­nam-style. An ex-cheer­lead­er on staff did the cho­reo­graphy. “We had prac­tice,” he says. “Sev­er­al prac­tices.” As for the scantily clad wo­men in Blurred Vines, he says they were vo­lun­teers. “Look, the wine busi­ness, at the end of the day, too many people take too ser­i­ously,” Jordan says. “If you can’t have fun around wine, it’s a you prob­lem.”

Life is fun when you’re mak­ing money. Jordan has been run­ning the winery’s day-to-day op­er­a­tions since 2005 — after a wind­ing early ca­reer that in­cluded the Nav­al Re­serve, busi­ness school, law school, and start­ing his own law prac­tice. Jordan Vine­yard & Winery ships out more than 100,000 cases of wine each year, he says, and Wine and Spir­its re­cently named Jordan the second-most-pop­u­lar brand in the coun­try among the na­tion’s top res­taur­ants, even with its av­er­age res­taur­ant price of more than $100 per bottle. The wine has been a hit for a gen­er­a­tion; the Re­agan White House served it at the 1987 state din­ner for So­viet lead­er Mikhail Gorbachev.

The wine busi­ness alone isn’t fuel­ing Jordan’s polit­ic­al giv­ing, though. He says he made some tech­no­logy-stock bets in re­cent years that paid off big (he de­clined to say which com­pan­ies). He has also cofoun­ded a tech com­pany of his own, which makes an iPad app for res­taur­ants.

CLOAKED IN SECRECY

After the 2012 elec­tion, Jordan was flush, frus­trated, and look­ing for some­where “fun” to spend his money. He found his op­por­tun­ity when John Kerry va­cated his Sen­ate seat to be­come sec­ret­ary of State. Re­pub­lic­ans re­cruited Gab­ri­el Gomez — a hand­some 47-year-old former Navy SEAL who sup­por­ted im­mig­ra­tion re­form, ex­pan­ded back­ground checks for gun buy­ers, and gay mar­riage — to run in a spe­cial elec­tion for the seat. Gab­ri­el Gomez (Jes­sica Rinaldi For The Bo­ston Globe)

Gomez was ex­actly the kind of out-of-the-box can­did­ate the GOP’s eld­er states­men had been de­mand­ing in the wake of the 2012 de­feats. Yet weeks away from the June spe­cial elec­tion, it was only Demo­crat­ic groups that had in­ves­ted in the race, back­ing vet­er­an Demo­crat­ic Rep. Ed­ward Mar­key to the tune of mil­lions. The U.S. Cham­ber of Com­merce, the Koch broth­ers’ net­work, and Cross­roads all sat on the side­lines. “There was a lot more in­terest in na­vel-gaz­ing and pout­ing about 2012,” says Brad Todd, one of Gomez’s ad­visers, who pleaded pub­licly for help. “Our donor base was guilty of not be­ing will­ing to take its as­pir­in and get over its hangover.”

But Jordan was watch­ing closely. In early June, he asked Re­pub­lic­an poll­ster John McLaugh­lin to sur­vey the con­test for him. The two had teamed up a few months earli­er, along with con­ser­vat­ive act­iv­ist Dick Mor­ris, on a poll of His­pan­ic-Amer­ic­ans about im­mig­ra­tion. On June 4, McLaugh­lin went in­to the field, on Jordan’s dime, and came back with the res­ults the next day: Mar­key, 45 per­cent; Gomez, 44 per­cent. “It was win­nable,” McLaugh­lin says. Pa­per­work was filed that day, and a su­per PAC was born. “It was a res­cue mis­sion on the fly,” Jordan says. “Four days be­fore, five days be­fore go­ing on the air, I had no idea I was even go­ing to do it.”

Jordan quickly as­sembled a polit­ic­al team. McLaugh­lin would serve as poll­ster. Sheena Tahilramani, Rove’s former chief of staff, would be his spokes­wo­man. Rick Wilson, a Flor­ida-based strategist, would cut the ads. Cleta Mitchell, a prom­in­ent GOP law­yer, would handle leg­al mat­ters. The group was giv­en a de­cept­ively non-Re­pub­lic­an name: Amer­ic­ans for Pro­gress­ive Ac­tion.

The date on the su­per PAC fil­ing was key. Be­cause it came less than three weeks be­fore Elec­tion Day, Jordan wouldn’t have to be re­vealed as its fun­der un­til after the elec­tion. Jordan in­sists this was a “co­in­cid­ence.” “I’m not say­ing I was dis­ap­poin­ted by it. And I’m not say­ing I wouldn’t do it that way,” he says now. “But in this case, it truly wasn’t [in­ten­tion­al].” As for the Demo­crat­ic-sound­ing name, he says, “Cleta Mitchell says you’ve got to have a name. I’m like, ‘Oh, shit, I’ve got to think of a name.’ “¦ I thought of that in the shower.”

Late-night con­fer­ence calls were sched­uled to go over the latest polling and stat­ist­ics from the field. “We would be on the phone, mid­night East Coast time, go­ing through the data,” McLaugh­lin says, “what was good, what was bad.” Des­pite a blitz of Jordan-fun­ded ads, the polls soon took a turn for the worse. Demo­crats were on the air, too, and the party faith­ful were co­ales­cing be­hind their nom­in­ee. Mar­key had widened his lead by June 19, ac­cord­ing to in­tern­al-polling res­ults provided by McLaugh­lin. They can­celed a fi­nal series of ads the week­end be­fore the race, and Jordan re­fun­ded him­self $273,000.

All the while, Jordan’s role re­mained cloaked in secrecy. As the ads filled the Mas­sachu­setts air­waves, the mys­tery of who was be­hind them grew. There was little to go on — just the name of Nancy Watkins, the GOP treas­urer who had signed the pa­per­work, and Tahilramani, the spokes­wo­man. Fi­nally, on June 21, four days be­fore the elec­tion and two days after the poll that caused them to pull the plug, Jordan outed him­self to The Wall Street Journ­al as the sole con­trib­ut­or. “Here I saw an Amer­ic­an hero run­ning in a close race in a tough state while get­ting ab­so­lutely poun­ded by Demo­crats throw­ing everything they could at him,” Jordan told the pa­per. “I just couldn’t sit by and watch and leave him alone while the es­tab­lish­ment Re­pub­lic­an groups de­cided to sit on their hands and just leave him on the beach.” Jordan gave me much the same ra­tionale: “It’s a Navy thing, first of all,” he said. “That’s hard to ex­plain.”

Jordan had blown through more than $1.4 mil­lion in two weeks on a los­ing ef­fort — and he loved every second of it. “I nev­er had any il­lu­sions about the prob­ab­il­ity of suc­cess. At the same time, some­body has to try, and you nev­er know. You lose 100 per­cent of the shots you don’t take, so why not do it?” he says. “And I’ve al­ways thought it would be fun to do, and I had a great time do­ing it, frankly.” Now, Jordan says that the Gomez race was just the be­gin­ning — a $1.4 mil­lion “po­ten­tial ice­berg tip” of fu­ture polit­ic­al ef­forts.

THE SPLINTERING OF SUPER PACS

At the same time Jordan was help­ing Gomez, Tom Stey­er was tap­ping his per­son­al for­tune to de­feat him. The Cali­for­nia-based re­tired hedge-fund in­vestor had cre­ated a su­per PAC of his own, Nex­t­Gen Cli­mate Ac­tion, to elect can­did­ates who prom­ised to ad­dress cli­mate change. Stey­er spent mil­lions in 2013, in­clud­ing in the Mas­sachu­setts Sen­ate race and the Vir­gin­ia gov­ernor’s race. He is now plot­ting a re­por­ted $100 mil­lion push in the 2014 elec­tions — half from him, half from oth­er like-minded donors.

“If you’re a busi­ness lead­er who wants to make a dif­fer­ence on policy is­sues, it may make sense to start your own or­gan­iz­a­tion.”

Every­where you look these days, wealthy donors are, like Jordan, tak­ing a DIY ap­proach to their polit­ic­al act­iv­ism. Bloomberg has star­ted his own an­ti­gun group. Mark Zuck­er­berg and oth­er tech elites wanted im­mig­ra­tion re­form, so they launched their own ad­vocacy arm. Joe Rick­etts, the founder of TD Amer­it­rade, es­tab­lished End­ing Spend­ing, a su­per PAC and a non­profit that seek to rein in the fed­er­al debt. “If you’re a busi­ness lead­er who wants to make a dif­fer­ence on policy is­sues, it may make sense to start your own or­gan­iz­a­tion,” says Bri­an Baker, pres­id­ent of the End­ing Spend­ing en­tit­ies and a polit­ic­al ad­viser to Rick­etts. “That is the clas­sic hall­mark of an en­tre­pren­eur.”

The world of the polit­ic­ally act­ive su­per­rich is small. They tend to con­greg­ate and com­mu­nic­ate to­geth­er. Bil­lion­aire hedge-fund in­vestor Paul Sing­er, for in­stance, is a be­ne­fact­or of End­ing Spend­ing ($350,000 in March 2014) and Amer­ic­an Cross­roads ($250,000, again in March 2014). But he has also seeded a su­per PAC of his own, the Amer­ic­an Unity PAC, ded­ic­ated to elect­ing pro-gay-rights Re­pub­lic­ans.

One com­mon­al­ity among these men of means (and it’s al­most all men) is their pas­sion for polit­ics. They want to do more than donate; they want to shape events. “More and more you can find that, as a com­mit­ted, in­formed in­di­vidu­al donor, you can as­semble the right kind of tools to be ef­fect­ive and move num­bers in cam­paigns,” says Wilson, the GOP con­sult­ant who de­signed Jordan’s pro-Gomez ads. And un­sur­pris­ingly, the su­per-wealthy tend to be­lieve they are rich for a reas­on: their smarts. “If you read enough, like what goes on in cam­paigns, and you read all the trade journ­als, it isn’t very hard,” Jordan says. “It’s not brain sur­gery.”

Go­ing it alone has po­ten­tial draw­backs, of course. Rich busi­ness­men are, al­most by defin­i­tion, polit­ic­al novices. They are at risk of sad­dling up to a con­sult­ant who can take them to the clean­ers, or mis­judging the im­pact their money can have in a par­tic­u­lar race. In­deed, some es­tab­lish­ment GOP op­er­at­ives have scoffed at Jordan’s Gomez in­vest­ment as fool­hardy. Mar­key, they point out, won by a com­fort­able 10 per­cent­age points.

Still, the fur­ther splin­ter­ing of the su­per PAC uni­verse now seems in­ev­it­able. And it rep­res­ents a chal­lenge to the re­l­at­ive power of polit­ic­al parties and large out­lets that, like Cross­roads, are not donor-led. For ex­ample, the Kochs, lead­ers of one of the ori­gin­al do-it-your­self donor ef­forts, have lapped Cross­roads so far in the 2014 Sen­ate races. The Koch-linked Amer­ic­ans for Prosper­ity and Free­dom Part­ners had spent a com­bined $23.5 mil­lion on ads in Sen­ate races as of late April, com­pared with $2.6 mil­lion for Cross­roads, ac­cord­ing to a Demo­crat­ic source track­ing ad buys. (The Cross­roads su­per PAC’s fun­drais­ing did pick up dra­mat­ic­ally in March, post­ing its best month since the 2012 elec­tions.)

Just this week, Jordan launched his latest ven­ture, fund­ing ads in Ore­gon’s May 20 GOP primary on be­half of Mon­ica We­hby, a pe­di­at­ric neurosur­geon. Jordan sees her as “a sleep­er” can­did­ate against Demo­crat­ic Sen. Jeff Merkley, es­pe­cially giv­en the state’s dis­astrously or­gan­ized Obama­care ex­change. “The nat­ur­al at­mo­spher­ics are right,” he says. Jordan has giv­en his money through Ne­wRe­pub­lic­an.org, a su­per PAC or­gan­ized last year by GOP op­er­at­ive Alex Cas­tel­lanos; the wealthy De­Vos fam­ily is the oth­er main con­trib­ut­or. As he was in the Mas­sachu­setts elec­tion, Jordan is heav­ily in­volved in the su­per PAC’s strategy. “It will be hard for any­body to get a big check out of me to a su­per PAC that I’m not in the middle of,” Jordan says. “Mostly, be­cause I don’t trust them.” (He did say he might carve out an ex­cep­tion for the Kochs.)

Jordan doesn’t have a horse yet in the 2016 pres­id­en­tial race, but Sen. Rand Paul of Ken­tucky in­trigues him. “I ad­mire what he is do­ing in terms of broad­en­ing the party’s ap­peal,” Jordan says. In mid-March, he had men­tioned New Mex­ico Gov. Susanna Mar­tinez to me as an­oth­er in­triguing fig­ure; sure enough, by late April, she had come to his chat­eau for a fun­draiser and stayed the night in one of his guest cot­tages. She was a bright ex­cep­tion, he says, to his gen­er­al rule that pols are an “over­dose of un­der­whelm.”

Whatever’s next, Jordan is sure to be in the cock­pit, as he is in his planes. “If you have the abil­ity to do it, why not do it?” he says. “Polit­ic­al cam­paigns are so much fun.”

What We're Following See More »
TAKING A LONG VIEW TO SOUTHERN STATES
In Dropout Speech, Santorum Endorses Rubio
3 days ago
THE DETAILS

As expected after earlier reports on Wednesday, Rick Santorum ended his presidential bid. But less expected: he threw his support to Marco Rubio. After noting he spoke with Rubio the day before for an hour, he said, “Someone who has a real understanding of the threat of ISIS, real understanding of the threat of fundamentalist Islam, and has experience, one of the things I wanted was someone who has experience in this area, and that’s why we decided to support Marco Rubio.” It doesn’t figure to help Rubio much in New Hampshire, but the Santorum nod could pay dividends down the road in southern states.

Source:
&#8216;PITTING PEOPLE AGAINST EACH OTHER&#8217;
Rubio, Trump Question Obama’s Mosque Visit
3 days ago
WHY WE CARE

President Obama’s decision to visit a mosque in Baltimore today was never going to be completely uncontroversial. And Donald Trump and Marco Rubio proved it. “Maybe he feels comfortable there,” Trump told interviewer Greta van Susteren on Fox News. “There are a lot of places he can go, and he chose a mosque.” And in New Hampshire, Rubio said of Obama, “Always pitting people against each other. Always. Look at today – he gave a speech at a mosque. Oh, you know, basically implying that America is discriminating against Muslims.”

Source:
THE TIME IS NOW, TED
Cruz Must Max Out on Evangelical Support through Early March
3 days ago
WHY WE CARE

For Ted Cruz, a strong showing in New Hampshire would be nice, but not necessary. That’s because evangelical voters only make up 21% of the Granite State’s population. “But from the February 20 South Carolina primary through March 15, there are nine states (South Carolina, Alabama, Arkansas, Georgia, Oklahoma, Tennessee, Kentucky, Mississippi, and North Carolina) with an estimated white-Evangelical percentage of the GOP electorate over 60 percent, and another four (Texas, Kansas, Louisiana, and Missouri) that come in over 50 percent.” But after that, he better be in the catbird’s seat, because only four smaller states remain with evangelical voter majorities.

Source:
CHRISTIE, BUSH TRYING TO TAKE HIM DOWN
Rubio Now Winning the ‘Endorsement Primary’
3 days ago
WHY WE CARE

Since his strong third-place finish in Iowa, Marco Rubio has won endorsement by two sitting senators and two congressmen, putting him in the lead for the first time of FiveThirtyEight‘s Endorsement Tracker. “Some politicians had put early support behind Jeb Bush — he had led [their] list since August — but since January the only new endorsement he has received was from former presidential candidate Sen. Lindsey Graham.” Meanwhile, the New York Times reports that fueled by resentment, “members of the Bush and Christie campaigns have communicated about their mutual desire to halt … Rubio’s rise in the polls.”

Source:
7 REPUBLICANS ON STAGE
Carly Fiorina Will Not Be Allowed to Debate on Saturday
2 days ago
THE LATEST

ABC News has announced the criteria for Saturday’s Republican debate, and that means Carly Fiorina won’t be a part of it. The network is demanding candidates have “a top-three finish in Iowa, a top-six standing in an average of recent New Hampshire polls or a top-six placement in national polls in order for candidates to qualify.” And there will be no “happy hour” undercard debate this time. “So that means no Fiorina vs. Jim Gilmore showdown earlier in the evening for the most ardent of campaign 2016 junkies.

Source:
×