While it has been an open secret for several years that Donald Trump was once a heavy Democratic donor, a deeper analysis of campaign records shows that the real estate billionaire’s contributions skewed even further left during the 2006 mid-term election, the crucial contest that put Harry Reid and Nancy Pelosi in power and arguably helped pave the way for Barack Obama’s political agenda.

Between 1989 and 2010, The Donald gave $314,300 to Democratic groups and candidates and $290,600 to Republicans, according to a Daily Caller analysis of records maintained by the Center for Responsive Politics.

But Trump’s donation gap was even larger during the mid-2000s, which saw the end of Republican congressional majorities and the ascendance of the Democratic party.

Overall in the 2006 election cycle, Trump and his son, Donald Trump Jr., donated $77,200 to Democrats versus only $24,250 on Republicans. Looking back to the 2004 cycle, the pair donated $40,500 to Democrats and only $17,250 to the GOP.

A large share of Trump’s donations to Democrats were given to congressional committees dedicated specifically to gaining majority control of Congress. And that they did. Democrats took control of both houses of Congress for the first time since 1994 by gaining 31 seats in the House and increasing the Democratic caucus in the Senate by six.

Records show that in June 2006, Trump donated $20,000 to the Democratic Congressional Campaign Committee. That was in addition to the $5,000 he sent in April 2005 to the Democratic Senatorial Campaign Committee. At the same time, Trump Jr. gave the two Democratic committees a total of $22,500.

While the Trumps spent nearly $50,000 to elect congressional Democrats, they donated only $1,000 to the National Republican Congressional Committee (NRSC).

But perhaps the worst outcome that election for Republicans was that Pelosi and Reid became Speaker of the House and Senate Majority Leader, respectively. The pair made a formidable team and did heavy lifting to ensure that Obama was elected in 2008 and that much of his agenda — including Obamacare — was put in place.

If Trump does choose to run — a decision on which he will announce on June 16 — he’ll face a field of 15-plus Republican hopefuls. He’ll also be fighting almost immediately for the life of his campaign. The Republican National Committee has changed its rules this cycle by limiting party debates to the top 10 hopefuls in the polls. The party is taking the unprecedented move in order to limit exposure to dark horse candidates.

Trump finished eighth in a Quinnipiac poll released last week. The first debate will be held Aug. 6 and will be hosted by Fox News.

If Trump makes that debate stage and if he becomes a big enough threat to primary front-runners — former Florida Gov. Jeb Bush, Florida Sen. Marco Rubio, and Wisconsin Gov. Scott Walker — his past support the GOP’s mortal political foes will almost certainly become the topic of debate.

Topping the flamboyant former TV celebrity’s roster of Democratic benefactors is scandal-plagued New York U.S. Rep. Charlie Rangel. Records show the Harlem-based Democrat has received $26,250 in Trump cash since 1989. Trump Jr., has given heavily to Rangel as well.

New York Sens. Kristen Gillibrand and Chuck Schumer have received $7,950 and $7,900, respectively, in Trump money. And two liberal lions, former Massachusetts Sens. John Kerry and Ted Kennedy, received $5,500 and $5,000.

Trump also arguably helped enable Obamacare in another way — albeit before the health law was a twinkle in any liberal’s eye. Trump supported two of its most ardent supporters in Reid and New York U.S. Rep. Anthony Weiner. He donated $7,400 to the Nevada Democrat. Among those contributions is $2,400 Trump gave Reid ahead of his contentious 2010 run against Sharron Angle, a tea party favorite.

Trump also gave $4,300 to Weiner, a dogged supporter of Obamacare who was forced to resign his seat following a sexting scandal.

Since its passage, Trump has called Obamacare “a filthy lie” and said that it would shut down the country. Though Obamacare was not on the radar when Trump made his donations, Democrats have long sought centralized control of the American health care system.

But perhaps most damaging to Trump’s campaign — if he chooses to embark on one — is the money he’s given to Hillary Clinton and other Clinton family endeavors. Trump donated more than $4,100 to the likely Democratic nominee in 2002, 2005, 2006 and 2007, records show. Trump Jr. gave the former first lady $6,100 in 2006 and 2007.

Those donations pale in comparison to other support Trump has given the Clinton empire. It was recently revealed that he gifted the Clinton Foundation at least $100,000, according to the Clinton Foundation website. The always outspoken Trump defended the donation, saying that the Clintons “kissed [his] ass” for the dough.

Trump’s donations to high-profile Democrats isn’t limited to those on the national stage. Not included in the Center for Responsive Politics’ database is a $50,000 contribution Trump gave in December 2010 to former Bill Clinton and Obama White House official Rahm Emanuel for his successful Chicago mayoral bid.

Perhaps atoning for what many Republican primary voters will consider to be grave political sins — donating to Reid, Clinton, and Schumer, who has been tapped to lead Senate Democrats when Reid retires — Trump has contributed $358,700 exclusively to Republicans since 2011, mostly in large-dollar donations to political action committees.

It was around that time that Trump became a vocal critic of Obama’s and began seeking information about his birth certificate. The aggressive approach helped win Trump solid support among some conservatives.

Before 2011, Trump’s $290,600 in donations to Republicans went to a smattering of candidates, many of whom were from his home state of New York.

Records show Trump contributed $8,600 to Arizona Sen. John McCain, mostly for his 2008 presidential run. His second-biggest GOP benefactor wasn’t exactly a conservative stalwart. Former Pennsylvania Sen. Arlen Specter received $8,300 from Trump between 1989 and 2008 — the year before Specter switched parties.

In 2010, Trump, who was a registered Democrat between 2001 and 2008, gave $50,000 to the Karl Rove-backed super PAC, American Crossroads. In 2012 he gave $100,000 to the Congressional Leadership Fund, a super PAC aimed at getting Republicans elected to the House.

In 2013, Trump gave $32,400 to the NRSC and sent $50,000 to Kentuckians for Strong Leadership, Kentucky Sen. Mitch McConnell’s super PAC. He gave another $32,400 to NRSC in 2014 and a similar donation to the Republican National Committee.

While a request for comment to Trump’s spokesman was not returned, in the past he’s defended his donations saying that it was smart to pick a winning horse.

“Everyone’s Democratic,” he told Fox News in a 2011 interview. “So what am I going to do — contribute to Republicans?”

“I’m not stupid,” he said then. “Am I going to contribute to Republicans for my whole life when they get heat when they run against some Democrat and the most they can get is one percent of the vote?”

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