The Lucky Libertarian


MikeFZiethlow / Pixabay

This long winter of our most definite discontent is finally over. Votes have been counted, chads have been…chadded…and Donald J. Trump is the next President of the United States as of January. The House is firmly in the hands of the GOP, while the Senate also rests within the control of the Republicans.  For the Libertarian Party, it has been a strange and interesting year, filled with peaks and valleys. (The rest of the intro to be written after returns are in).

The last few days have been filled with post mortems, criticisms and forward looking strategy prescriptions for the losers, as well as denouncements, finger-pointing and blame, as the coming weeks will continue to be. This is the nature of electoral politics, with the aftermath being somewhat predictable within certain limits. For the Libertarian Party, it has been perhaps the strangest cycle of its 45-year existence.  Having fielded maybe the most experienced ticket in the field, with two former governors serving as the party’ standard-bearers, the LP began this cycle with perhaps the most promise for the future of the party since it was established in 1971. In some ways, the ticket lived up to that promise. With town hall presentations hosted by CNN and Fox’s John Stossell, Johnson/Weld received unprecedented media attention, eventually resulting in a record showing on election day; three percent of the popular vote, as well as over four million votes, more than tripling the showing of any the previous record for LP presidential candidates.

Yet, the campaign ultimately fell short of its established goals. There was no inclusion in the debates hosted by the extremely partisan Commission on Presidential Debates, no huge influx of campaign contributions from parties disgusted with the prospect of what a Trump presidency might do to the GOP, and, most importantly, no 5% of the popular vote on election night – the grand chimera of third-party politics. To be fair to the top of the ticket, Gary Johnson could not have been expected to provide these things. He was, although the fairly successful two-time Governor of New Mexico, a virtual unknown from a small border state. Although, in 2012, Johnson and his running mate, retired California judge Jim Gray, had run the most successful libertarian candidacy in the party’s history, they still only managed roughly one percent of the popular vote, for a total of roughly 1.28 million votes. The man who was supposed to make the difference in 2016 was the man at the bottom of the ticket.

That man is former Massachusetts Governor William Floyd Weld.

Bill Weld: The Man Who Would Be VP

Bill Weld was never the popular choice to be the Vice-Presidential candidate of the Libertarian Party.  At the May 2016 Libertarian National Convention in Orlando, well was a virtual unknown to the gathered delegates, with a list of positions that bred suspicion. Of greatest concern were his notions regarding eminent domain, gun control and his support of George W Bush’s interventionist foreign policy. To his detractors, and there were many, Weld had much to prove, and a short time to prove it.  Unlike the Republican and Democratic fields, the LP does not select their candidate via a series of primaries and caucuses, mostly due to arcane state-by-state rules for ballot access that also determine who may actually appear on primary ballots. As a result, although a few states actually hold primaries, the candidates for the LP ticket are decided at the convention – separately.

Nigel Parry/CNN











As is widely known, Weld hardly had an easy time securing the number two spot on the ticket. While he was clearly Johnson’s choice, the delegates had other ideas. In the first round of voting, no contender received the majority needed to secure the nomination, causing Johnson to plead with delegates to grant him his preferred choice. Libertarians being a proudly contentious lot, many instead began to rally behind second-place finisher Larry Sharpe, with first round contenders Derrick Grayson and Will Coley directing their delegates towards Sharpe in order to stop Weld, who had received 49% during the first vote. Without the support of Alicia Dearn, who had been eliminated during first round voting, Weld would likely have lost the second vote to Sharpe. As it was, Weld barely received the necessary majority, and Johnson had his man.

The question that day, as it still remains, is who exactly did Johnson and the Libertarian Party get? Who exactly is Bill Weld? To understand why this man so troubled libertarians during his time as their Vice-Presidential candidate, the man himself must be understood.

Bill Weld: The Rise and Fall of a Brahmin

In 1990, a brash former Federal prosecutor had the somewhat daft notion to run as a Republican to replace outgoing Massachusetts Governor Michael Dukakis. The idea was daft because Republicans made up less than 14% of the Massachusetts electorate, with no Republican having held the office since 1970. Making matters worse, the man wasn’t even the choice of the state’s party establishment, with that honor belonging to state House Minority leader Steven Pierce. At last Pierce, a known quantity to the voters of Massachusetts, could be expected to give Democratic nominee John Silber, the respected president of Boston University, a good showing as opposed to this prosecutor who had never run for anything.

But Bill Weld was no normal political neophyte. He was a good, old-fashioned Boston Brahmin, scion of an old family who had helped shape the character of Massachusetts since his ancestors came over on the Mayflower; he was, for crying out loud, married to a great-granddaughter of Teddy Roosevelt. A Harvard educated Rhodes Scholar, Weld cut his legal teeth on the House Judiciary Committee’s Watergate inquiry, where he helped take down a President of his own party. While serving on the inquiry, he formed a lifelong friendship with one Hillary Rodham; a friendship that in later years would cause the LP no end of grief. Having garnered the notice of then U.S. Associate Attorney General Rudy Giuliani, Weld was appointed to the office of U.S. Attorney for Massachusetts in 1981 by President Reagan. Having waged holy war against banking corruption and white-collar crime, Weld was promoted to the Justice Department’s Criminal Division in 1986, where among other things, he was responsible for the capture and prosecution of Manuel Noriega.

In 1988 Weld, along with Deputy Attorney General Arnold Burns, resigned in protest of alleged financial improprieties by then US Attorney General Edwin Meese. In July of that year, Weld and Burns testified against Meese before a select Congressional committee. Keep this point in mind, as it is important to understanding how Weld eventually ended up leaving the Republican Party. In any case, Meese’s career ended, and two years later, Weld was winning an improbable victory in the Massachusetts gubernatorial race. Both the public and business community reacted well to Weld’s first term, and in 1994. He was reelected with 71% of the popular vote. He had become a rising star within Republican circles, with several observers eyeing him as a future President. This was only reinforced when, in 1996, Governor Weld challenged incumbent Democrat John Kerry for his seat in the Senate, giving Kerry a competitive race in a year when Bill Clinton carried Massachusetts with over 60% of the vote.

In 1997, it all came tumbling down. Ironically Weld’s downfall began on a political high note. In July of 1997, President Bill Clinton nominated Weld as his choice to be US Ambassador to Mexico. What seemed at first a formality became a battle when the Republican Chairman of the Senate Foreign Relations Committee, North Carolina’s Jesse Helms, decided to block Weld’s nomination, having, in theory, taken exception with Weld’s liberal stances on abortion, gay-rights and the legalization of medical marijuana. In the background, Helms was in reality doing a favor for his good friend Edwin Meese, whose political career Weld had helped end. Despite the advice of the Clinton Administration, Weld decided to fight, resigning as governor and going on the attack. Ultimately, his actions cost the support of erstwhile supporters such as Senator Trent Lott, and Weld withdrew himself from consideration. Weld was no longer a GOP golden boy looked at as being a future President. His party had suddenly turned sharply to the right and left him behind.

A Bill Weld State of Mind: New York and the First LP Dalliance

If Weld’s story had ended there, it is possible that a very different Bill Weld would have appeared at the LP convention in 2016, if he appeared at all.  In 1997, he joined the law firm of McDermott Will & Emery, and in 2000, was named head of the firm’s NYC office. It was a homecoming of sorts for Weld; although his bloodlines make him the quintessential Boston Brahmin, he was actually raised in Long Island. In 2001, Weld joined the private equity firm of Jeffrey Leeds, with the firm being renamed Leeds Weld and Co. Having divorced Susan Roosevelt in 2002, Weld married writer Leslie Marshall, whom he had been rumored to have been seeing since 1998, the following year. Ever bored and always needing a challenge of some sort, in 2005, Weld set out to become the first man since Sam Houston to have served as the chief executive of two different states.

In April of that year, three-term Republican Governor George Pataki announced that he had decided not to seek a fourth term. Weld’s unlikely and maverick first run in Massachusetts appealed to some elements of the New York Republican Party. According the Patrick Healy of The New York Times, those elements viewed Weld as a combination of Pataki, Rudy Giuliani and Michael Bloomberg; just the type of dynamic character that would be needed in a race against the Democratic challenger, popular New York Attorney General Eliot Spitzer. His chief early opponent was John Faso, the erstwhile GOP Assembly Minority Leader.  At this stage of the race, Faso did not have widespread support for his candidacy, and it seemed that Weld would be the nominee.

In fact, Weld received the backing of the GOP county chairs of New York state, and the public endorsement of State Chairman Stephen Minarik. There was even the rumor of an endorsement from Pataki. It was during this early stage that Weld decided to stack the deck in his favor, realizing that the support of the Republican establishment alone would not serve to defeat Spitzer. In April of 2006, Weld sought and received the nomination of the Libertarian Party of New York, in an effort to forge a right-leaning coalition that would be able to deny Spitzer the seat. In the meantime, he offered the second spot on the ticket to Faso, who declined. Faso determined that Weld’s support was not as robust as it seemed on the surface, and he continued to court those counties that had withheld their endorsements of Weld.

Having been denied by Faso, Weld tapped NY Secretary of State Christopher Jacobs as his running mate at the state Republican convention.  This proved somewhat problematic, as Jacobs had made a small donation to Spitzer’s gubernatorial run the previous year. The rumored endorsement from Pataki never came, and Faso was able to run with Jacob’s donation to Spitzer, causing Weld’s most ardent supporter, Minarik, to urge Weld to withdraw his candidacy in the name of party unity. Weld complied, Faso won the nomination, and went on to be crushed by Spitzer in the general election.

For the second time, the GOP had left Weld in the lurch. He was not the only party to be left hanging, however. Having failed to secure the Republican nomination, Weld withdrew entirely from the race, foregoing his commitment to the LPNY, leaving the state Libertarian Party with no candidate.

Bill Weld: “Libertarian for Life”

One can only imagine what was going through the mind of William F. Weld when he received the call from Gary Johnson asking if he was interested in being the Vice-Presidential nominee for the Libertarian Party. He had gone back to McDermott Will & Emery after his failed New York gubernatorial bid, had tried his hand at writing novels, moved back to Boston where he became a partner at Mintz, Levin, Cohn, Ferris, Glovsky, and Popeo, and likely considered his career in politics over for good. He was 70 years old, an afterthought in GOP circles, and but for Johnson, likely to never have been heard from again.

Never a fit for the contemporary social conservatism of the GOP, Weld saw this call as an opportunity to reinvent himself and regain relevance in the public eye as a champion of laissez-fare. He declared himself a Libertarian for life, free from the shackles of the moral authoritarianism of his former party, and ready to go into battle with Johnson, a contemporary from his time as governor whose record he greatly respected. However, unlike the patrician Weld, Johnson was not a polished, made for primetime candidate. A likeable, but socially awkward everyman, Johnson is a study in pulling oneself up by his own bootstraps and achieving a string of admirable successes, but also the kind whose worth is lost in translation. And unlike Weld, the Rhodes Scholar/attorney/governor/investment banker/novelist with a wide variety of interests, Johnson was disinterested in discussing policy in any great depth, preferring to preach the virtues of foundational principles from which he believed the proper policy would flow. Such an approach obviously worked well for Johnson in New Mexico, where he was notorious for giving aides and legislators five minutes to explain their proposals, but it did not play well on the national stage.

Over the course of the campaign, a seemingly frustrated Weld seemed to draw farther and farther away from Johnson, exerting his independence from the overall strategy. He continued to praise Johnson, calling him a friend that he greatly admired, a man of integrity and understated intelligence who was absolutely the right person for the job. This was the proper thing to do, of course, as the role of the second person on the ticket is to praise the virtue of his candidate while highlighting the deficiencies of the opponents. It soon became abundantly clear that even if Weld liked and admired Johnson personally, he had a dim view of his virtues as a candidate, making his praise of his cohort so much lip service.

As previously noted, Weld is a gifted politician, and although he frustrated the Libertarian base to no end, he seemed to always have a plausible explanation for his maddening tendency to stray off message. His statements were taken out of their full context by a media bent on marginalizing the impact that third parties would have on this bizarre election. He was simply taking the point of view of an experienced prosecutor, and educating the public on the lack of the quality of evidence it would take to prosecute Mrs. Clinton. There were other explanations for his behavior, and despite the frustration the base found mounting within themselves, these explanations managed to temporarily mollify the troops because there was an air of plausibility to them. Yet, the mainstream media continued to put forth that Weld had lost faith in the ability of the ticket to achieve even modest objectives such as five percent of the popular vote in the general election, signaling voters to concentrate on ensuring a defeat my Mr. Trump. Perhaps even more weary of the dishonest coverage of the campaign in general than they were of Weld, many libertarians rolled their eyes at these assertions, until a scant week before the election, this happened:

It was clear, at this point, that Weld was not definitely not looking out for the interests of the ticket, Nor, as it turns out, other tickets either.

Who Is Thom Simmons? – Bill Weld and the Soul of Massachusetts

While Presidential tickets often receive the bulk of the attention, one of the most interesting things about election cycles is often the downparty candidates; those running for state and local offices, as well as those seeking seats in the United States Senate and House of Representatives. The former is important in expanding and maintaining a party’s base, while the latter is critical in providing support to a President of their party. There are, of course, no members of the LP in Congress. With the increased publicity afforded the party in 2016, this cycle may have been an excellent chance to put the party’s first member on Capitol Hill. One of the candidates with the most promise was one Thomas T. Simmons of Shelburne Falls.

Thom Simmons, by all accounts, is an interesting gentleman. An Auxiliarist in the Holyoke Flotilla of the United States Coast Guard, Simmons is graduate of Hofstra University. Simmons holds both a Bachelor of Science in Business and Economics, as well as a law degree. Not only has Simmons made a name for himself in the professional circles of Massachusetts, he has also been a tractor-trailer driver and a commercial shellfisherman. Simmons has served as an attorney representing Vietnam veterans on claims against Agent Orange exposure, and as Administrator of the Martha’s Vineyard Planning and Economic Development Commission. He also served as a professor of Business and Economics at Greenfield Community College, where he helped develop a module in Sports Economics, as well as serving as a faculty advisor to Springfield, MA’s Grinspoon Entrepreneurial Initiative, which assists Western Massachusetts area students in obtaining the startup capital to establish new businesses in the region.

Simmons for Congress

Staff/The Register

Simmons additionally served on the Shelburne Conservation Commission, as well as on the boards of directors of two local HIV service initiatives. Along with his partner, he has adopted six children. A longtime member of the Libertarian Party of Massachusetts, Simmons is exactly the type of candidate that the party needs to expand its positive profile; well educated, accomplished, and active within his local community. Having been a laborer, a professional and an academic, it is likely that Simmons understands the needs of several cross-sections of society. More importantly, Simmons had the sort of experience that potentially translates well to advocating for the principles of liberty in the formation of public policy.

The 1st Congressional District of Massachusetts is a sprawling region that covers more than one-third of the area in the state. Unlike the gleaming paean of cosmopolitanism that is Boston, the district is largely rural, with Springfield serving as its largest city. The college graduation rate for the district is roughly 27%, not all that surprising for a largely rural area. Unemployment is relatively high, at 10.7%. Median household income for the district is $49,270, some 30.2% lower than the state median income of $70,628. It is relatively safe to say that the district could use some positive development.

Prior to the election on November 8, the 1st District has been represented in the House for 28 years by one Richard Neal, the Democratic former mayor of Springfield. It goes without saying that an incumbent who has served fourteen straight terms enjoys a good deal of popularity within his district, and that it would take an extraordinary challenger to have a chance to unseat him. Additionally, the district trends D+14 on the Cook Partisan Voting Index, suggesting that the district tends to vote Democrat 14 percentage points more than the nation as a whole. Yet, as recently as three weeks prior to the election, Simmons was polling at 41% in the race against Neal.

It would be reasonable to assume that with such an opportunity to elect the LP’s first Congressman at hand, a combination of the national and state campaigns, as well as LPMASS would lavish attention and resources to Simmons’ cause. Unfortunately, that assumption would be incorrect. According to sources familiar with the situation, while LPMass extended to Simmons the legal maximum the state organization was allowed to give, attempts to receive funding from the LNC and the national campaign were met with hostility, as it was decided that the focus should be maintained on the national campaign. Additionally, the state campaign coordinator, Heather Mullins, met pleas to arrange grassroots efforts in support of Simmons’ candidacy with disdain and derision, before abandoning the Johnson/Weld campaign at the eleventh hour to join the national tour of Libertarian personality Adam Kokesh.

This would be tragic in and of itself if this were any other state, but it happened in the state that Bill Weld calls home. Reportedly, Weld took it amiss when informed that Simmons had been a member of the party for a much longer period of time than he had, and understood the issues relevant to his local district. While there is certainly some validity to the LNC’s reported assertion that they did not have the time to properly vet downparty candidates in every state, there can be little excuse for failing to do so with a competitive candidate for US Congress in the Vice-Presidential candidate’s home state. On Election Night, Simmons, who had polled so well while toiling courageously on his own, drew 9% of the 1st District’s vote. While there is no guarantee that assistance from his party would have won the seat, 41% does not drop to 9% if that support had come. In short, Thom Simmons got screwed.

The Final Act of Bill Weld

The election is over, so what does any of this mean? Why is it important, and more accurately, why is it important to the future of the Libertarian Party? Governor Johnson has delivered the best electoral result in the history of the party, however disappointing many may view it, and gone off into retirement. Moreover, most observers already knew that Bill Weld is a particularly complex individual, so a seeming retrospective adds little to (or, for that matter, subtracts from) their opinion of him. Many feel that it’s time for Weld and the LP to move on from one another, with the party looking towards its future,

Life is, of course, rarely this simple. Weld is a proud member of LPMass, and likely intends to remain so. In fact, TLL has learned from a credible source that Weld intends to challenge incumbent Democrat Elizabeth Warren for her seat in the United States Senate in the midterm elections of 2018. With this information in mind, many of Weld’s more peculiar actions during the campaign take on a new light. There were times, it seemed, when he seemed to be running two entirely different campaigns with cross-purposes; one to further the success of the ticket, and one that seemed entirely disengaged. Perhaps, in light of this likely Senate run, a new analysis of these actions must be undertaken.

Many reasons have been given for Weld’s strange patterns of behavior, and admittedly, there is some merit to them. His vociferous defenses of Hillary Clinton have been attributed by some to his longstanding friendship with Mrs. Clinton; a gentleman refusing to allow the depravity of politics to damage his standing with a longtime acquaintance. There is some truth to that, yet, Mr. Trump is also a longterm friend of the Clintons, and had no issue going on the attack. Yet others view Weld’s behavior as that of a former prosecutor unmoved with the evidence of Mrs. Clinton’s corruption, deeming it as falling short of the prosecutorial burden of proof. There is some truth to that as well. Finally, there are those who believe that Weld was engaged in a strategy of triangulation, whereby Johnson took the baton of going after Clinton, while Weld served as the focal point of the battle against Trump. There is some validity to this as a strategy, and It might have even been effective had Weld simply attacked Trump without eliciting a stream of platitudes regarding his notions of “a wonderful public servant.”

Nuggets of truth do not, however, reveal the totality of truth, nor even the greater portion. A closer look suggests that the real driver behind Bill Weld’s seeming endorsement of the Democratic standardbearer lies in the 51% approval rating Senator Warren enjoys among the voters of Massachusetts.  Even for an experienced hand such as Weld, this is no insignificant mountain to climb. While Weld was held in high esteem by Massachusettsconc voters during his time as governor, and did reasonably well in his run against John Kerry, it has been a long while since he was relevant in Massachusetts politics in any meaningful way. The key to running a competitive, and perhaps winning, race would be to create a fusion of interests, running under the LP banner while attracting the votes of not only the minority Republican voters, but a goodly portion of Democrats as well. In short, Weld could not afford to attack Clinton because he could not afford to alienate the passionate liberal voters of Massachusetts.

AP Photo/Steven Senne

AP Photo/Steven Senne

At what point did Weld shift his focus from advancing the interests of the LP and its Presidential ticket towards laying the foundation for his own future ambitions? This question, of course, presupposes that he was ever concerned with the furtherance of the party to begin with. This is not to say that Weld wishes ill for the Libertarian Party; he does not. It is a more rational argument that he wishes for the party to grow, but in a manner consistent with his own interests. The strategy utilized by the campaign rested upon two difficult planks, which seemed achievable at the outset, but were ultimately revealed to be impossible. The first plank, as everyone knows, was to gain participation in the debates sponsored by the partisan Commission on Presidential Debates. The second plank, even more difficult in scope, was to concentrate on winning the electoral votes of key contested states such as Utah, Nevada and Johnson’s home state of New Mexico in order to deny majority of Electoral College votes to either major party candidate. The idea, of course, was to appear to the House of Representatives, who would decide the winner under such a scenario, a compromise between two historically unpopular candidates, making Johnson the alternative of choice.

In the early going, it seemed plausible that the ticket might make the debates, as voter discontent resulted in the duo reaching double digits in the major polls, despite, initially, a serious lack of national name recognition.  Too, it seemed that the electoral strategy had some legs, as Johnson’s numbers covered the spread between Clinton and Trump in some 20 states. However, as Johnson began to appear under the bright lights of the unprecedented media attention afforded the ticket, a series of well-chronicled gaffes and dismissive media opinion began to eat into his support, playing a role in diminishing poll numbers on the eve of the debates (in the opinion of this author, sample manipulation also played a part, but that is a matter for another time, perhaps). Without a chance to redeem themselves in the debates, the possibility of winning electoral devotes also evaporated. What began as an outside, but real shot at a pathway to victory, however improbable, disappeared. The further the poll numbers slipped, the more erratic and curiously disloyal Weld’s behavior became, with him declaring that his focus was now on keeping Trump out of the White House, and increasing his defenses of Mrs. Clinton.

Bill Weld’s Winter: The Legacy of a Wounded Lion

Before continuing, it should be noted that even in the best case scenario – an electoral surprise that sent the election to Congress – Weld had no realistic shot of assuming the Office of the Vice Presidency. While a House choice of President is chosen from among the three candidates with the most electoral votes, the Senate chooses the VP from among the two candidates whose ticket received the most electoral votes. The most Weld could have hoped for was some appointment in a Johnson administration. As such, one might rationally question the depth of an ambitious man’s commitment to an unwinnable cause, especially when other opportunities may avail themselves in the not-so-distant future.

It is perhaps easy to sympathize with Weld’s desire to see the Republican nominee denied a victory. Mr. Trump, after all, represented the party that left Weld behind. The blocked ambassadorial nomination, the abandonment of the NY Republican Party of his gubernatorial run – these are legitimate causes to hold grudges. It is also easy to see Mr. Weld as a preferable alternative to Elizabeth Warren. Does this author wish to see Ms. Warren denied the furtherance of her Senate career? Of course. Is Weld capable of defeating her? Perhaps; it would be no easy task, but he has scaled such a mountain before. The question then becomes; is a Bill Weld serving as the highest elected official of the Libertarian Party a good thing for the future of the party?

Consider this; a Senate victory in 2018 would make Weld the most visible, highest profile member of the Libertarian Party. For a party still fighting to define itself in the eyes of the American public, he would become that definition. Compromise, is of course, paramount to political success, but how much compromise can we, in all good conscience, bear? Bill Weld, when viewed under a microscope, is a wounded lion, desperately seeking to rewrite the story of his winter. As demonstrated by his actions in both New York and during the 2016 Presidential campaign, it is the LP that he is using as his pen. What sort of future will this novelist, unrestrained, write for us?

[Pic by Marc Garfinkel/Boston Herald]



Tarnell is an economist, entrepreneur and social observer. When he is not being a Lucky Libertarian, he is likely plotting to take over the world (and leave you alone) and singing romantic ballads to absolutely no one.