Inside campaign fundraising: Pelosi hits Chicago for Democrats; major GOP donor retreat in city

The COVID in-person political fundraising pause is over, and I’ve got a packed Chicago related round-up for you

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Speaker Pelosi Holds Weekly Press Conference On Capitol Hill

Speaker of the House Nancy Pelosi travels to Chicago next week for Democratic fundraising events.

Chip Somodevilla/Getty Images

WASHINGTON — The COVID in-person political fundraising pause is over, and I’ve got a packed Chicago related round-up for you, starting with a double play next week by House Speaker Nancy Pelosi, always a big draw for Chicago-area Democratic donors.


President Joe Biden headlined a mega dollar funder for the Democratic National Committee on Wednesday with Gov. J.B. Pritzker, but the well is far from dry. Pelosi returns next Thursday for a funder to benefit the Democratic Congressional Campaign Committee, the House political shop chaired by Rep. Sean Patrick Maloney of New York, who will also attend, along with Illinois Democratic Reps. Robin Kelly, the Democratic Party of Illinois chair; Raja Krishnamoorthi; Jan Schakowsky; Brad Schneider and Democratic donors Stephen Schuler and Andrea Schuler.

According to an invite obtained by the Sun-Times, the price tag for the event ranges from $5,000 to $50,000.


Next Friday, Schakowsky’s “Ultimate Women’s Power Lunch” annual event — this is the 21st — is back live for the first time since 2019 and is on track to be, once again, one of the biggest fundraising events in the state.

It can also be called the ultimate women’s professional, political and personal networking event because the crowd Schakowsky attracts — aside from the elected officials and candidates — includes some of the best connected folks around.

Ben Head, Schakowsky’s political director, told me well over 1,000 attendees are expected with three headliners: Pelosi, of California, who was the marquee draw for Schakowsky in 2019; first gentleman Doug Emhoff and Rep. Val Demings, D-Fla., leaving the House for a Senate run in a crucial swing state.

Schakowsky, from Evanston, attracts elected officials and candidates to her giant fundraiser because they want to try to widen their own contributor base by dipping into her donor pool.

Donor levels range from $100 to $5,800 for the funder, at the Hilton Chicago, 720 S. Michigan Ave.


State Rep. Delia Ramirez, D-Chicago, hits Capitol Hill on Monday for a funder to benefit her Democratic primary bid where Ald. Gil Villegas (36th) is her main rival in the new 3rd District drawn to yield a new Hispanic House member.

The tab ranges from $50 to $1,000.

Hosts include Rep. Jesus “Chuy” Garcia and Schakowsky from the Illinois delegation plus Reps. Mark Pocan from Wisconsin; Mondaire Jones, New York; Lucille Roybal-Allard, California; Nydia Velazquez, New York; Pramila Jayapal, Washington; Sylvia Garcia, Texas; and Teresa Leger-Fernandez, New Mexico.

Ramirez will also be doing some donor prospecting while in D.C., meeting with Democratic allied groups.

She will get another assist from Garcia, from Chicago, who endorsed Ramirez.

Before her event, Ramirez will stop at Garcia’s own funder, to be held, according to the invite, at the BOLD PAC townhouse near the Capitol. BOLD PAC is the Congressional Hispanic Caucus political operation, and hitting Garcia’s event gives Ramirez a chance to widen her fundraising network.

BOLD PAC is not going to endorse in the contest featuring two Hispanics in a safe Democratic district.


Russia is killing Ukrainians every day in its unprovoked war. That’s not stopping one Illinois MAGA candidate in the GOP Senate primary from featuring at a funder next Friday retired Lt. Gen. Flynn — an ex-national security adviser for President Donald Trump convicted of lying to the FBI about his contacts with Russia.

Flynn, pardoned by Trump, headlines a funder near O’Hare Airport for GOP Senate primary candidate Robert “Bobby” Piton. Piton, from Geneva, is an election denier who was active in the Trump-fueled Cyber Ninja election audit in Maricopa County, Arizona.

Flynn is now complaining because he says the Defense Department is trying to get back the $38,000 he got from the Russians in 2015 for a speaking gig — where he sat next to Vladimir Putin at a dinner.

Piton is one of seven Republicans in the GOP Senate primary. The “Fight Like A Flynn” price tag runs from $150 to $250.


Major RNC donors — at the high roller “Investors” tier — are being invited to an RNC summer retreat running from June 24 – 26 in Chicago. It will be an important showcase for GOP House, Senate and governor candidates as Republicans head into the November midterms with the tailwinds on their side.

This is a national event hosted by RNC chair Ronna McDaniel; co-chair Tommy Hicks; and finance chair Duke Buchan featuring many of the RNC’s best contenders, and according to an invitation obtained by the Sun-Times, former Trump senior adviser Kellyanne Conway.

Also on the list of “special guests” is Sen. Rick Scott, R-Fla., the chairman of the National Republican Senatorial Committee, the GOP Senate political shop.

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