With pressure mounting on all sides, Wednesday could prove to be a definitive day for Mayor Lori Lightfoot, just five months after she took office with a sweeping mandate to root out corruption and chart a progressive course while closing a massive budget deficit.

Lightfoot will have to scramble to resurrect her plan to allow legal cannabis sales, stymied by the latest aldermanic insurrection while facing a midnight deadline to avert a strike by the Chicago Teachers Union.

And Lightfoot now has less than a week to present her proposed 2020 spending plan — which must close a $838 million budget shortfall.

Lightfoot may have no choice but to ask aldermen to force Chicagoans to dig deeper into their pocketbooks by boosting a host of taxes and fees, including sure-to-be-unpopular a property tax hike.

But it is unlikely that a newly emboldened City Council will rubber stamp whatever the mayor’s proposal turns out to be.

Related: Tension boils over between aldermen and mayor as critics block appointment

One area where Lightfoot is certain to fall short Wednesday is her push to hike the city’s minimum wage to $15 an hour by 2021.

At a City Hall rally last month, Ald. Sophia King (4) told supporters that she expected her measure (O2019-4153) to get a final vote Wednesday — but the proposal has stalled after a hearing in the Workforce Development Committee Sept. 17.

King declined to answer questions Tuesday about why the measure had stalled, and Workforce Development Committee Chair Ald. Susan Sadlowski Garza (10) did not respond to a request for comment.

Erica Boland-Durosimi, the SEIU political coordinator for Chicago and Cook County, said the labor groups backing the push are frustrated that it has stalled. They fear it will be impossible to push through in November, as aldermen are consumed with crafting a budget, she said.

That effort will be complicated by the fact that aldermen will be asked to close an $838 million budget gap. City officials have yet to detail the budget impact of the measure, which would  also apply to city sister agencies and groups that get city funding.

“We need to pick up the pace,” Boland-Durosimi said.

Lightfoot remains committed to pushing the measure through the City Council, mayoral spokesperson Lauren Huffman said.

“To continue advancing protections for working families all across the city, Mayor Lightfoot has been clear from day one that we are committed to expediting the $15 minimum wage for Chicago,” Huffman said. “We are moving forward as planned and remain in close discussion with [the] City Council, advocates, and labor leaders to strike a balance and pass thoughtful legislation that includes input by all stakeholders and is fully accounted for in next year’s budget.”

Much of the debate at the September hearing centered on whether to force Chicago businesses to pay tipped workers $15, regardless of how much they earn in tips.

Chicago now allows employers to count tips on top of an hourly wage of $6.40 to ensure their workers are paid a minimum of $13 an hour, like all other workers in the city.

The state’s minimum wage will hit $15 per hour in 2025 under a law Gov. JB Pritzker signed less than a month after he took office.

The measure pending before the City Council would hike the minimum wage to $14 by the summer of 2020 and to $15 in 2021. After that, the wage would climb with inflation each July, with a cap of 2.5 percent, based on a study conducted by the Office of Labor Standards.

Aldermen will also get another chance to approve the appointment (A2019-60) of James Rudyk to be an alternate on the Zoning Board of Appeals.

Alds. Anthony Beale (9) and Raymond Lopez (15) used a parliamentary maneuver to delay his nomination at last month’s City Council meeting, automatically sending it to Wednesday’s meeting for a final vote. 

However, Lightfoot’s pick for planning commissioner is set for final approval. Maurice Cox (A2019-73), who led Detroit’s Planning Department until recently, navigated an at-times tense confirmation hearing to win the committee’s endorsement.

The council is also set to approve a plan (O2019-6955) that would allow any alderman to request that the City Council’s Office of Financial Analysis examine a proposal’s impact on the city’s budget.

Ald. Michele Smith (43),who authored the proposal with Ald. Pat Dowell (3) and Ald. Brendan Reilly (42), said the changes were designed to take the “brick off this office” created in May 2018.

Related: Aldermen green light plan to expand Office of Financial Analysis’ powers

The change is set to take place exactly one week before Lightfoot is set to unveil her red-ink drenched 2020 spending plan.

Lightfoot announced Tuesday that she planned to reduce that deficit by $25 million through an effort to boost tax and fees collection enforcement with vendors doing business with the city.  

A press release from Lightfoot’s office said the new accounts receivable system “will ensure frequent and comprehensive debt checks” and speed payment to vendors doing business with the city.

The change, which must be approved by the City Council, would be made possible by the approval of (O2019-6910) authorizing the Office of the Comptroller to enter into data sharing agreements with the state and other governmental entities supporting more comprehensive tax collection processes.   

The City Council’s Finance Committee gave that change the green light at its meeting on Thursday.

The following items are also set for the council’s approval on Wednesday:

  • O2019-7113 — A proposal to grant $1.55 million to Mercer Street Holdings Three LLC, which plans to renovate Leamington Foods at 3250 W. Roosevelt Road in the 24th Ward into Living Fresh Market. 
  • O2019-7011 — A proposal to use $62,000 in Open Space Impact Fee funds for the HarambeeCommunity Garden at 455-457 N. Waller Ave. in Austin.
  • O2019-6951 — A proposal to allow smaller supermarkets to sell booze starting at 8 a.m. on Sundays.
  • O2019-6973 — A proposal to make Argyle Street in Uptown a shared street permanently. [Our coverage]
  • O2019-7794 — A proposal to extend the pilot program that waives the fee for a city sticker to all veterans who are honorably or generally discharged from the armed services. [Our coverage]
  • O2019-5291 — A measure approving a $9.5 million city subsidy and $30 million loan to build a 102-unit complex on what was once the Cabrini-Green public housing complex in Old Town.
  • O2019-5591 — A measure to no longer require the surviving spouses of Chicago Police Department officers and Chicago Fire Department killed in the line of duty to pay property taxes to the city on their homes.
  • O2019-7043 — A proposal to spend $3.5 million from the Lawrence and Kedzie TIF to build a turf field, playground and natural landscape area to be used by Hibbard Elementary School, 3244 W. Ainslie St., and the Edison Regional Gifted Center, 4929 N. Sawyer Ave.
  • O2019-7100 — A proposal to revise the redevelopment agreement for the Marshfield Plaza shopping center in Morgan Park to allow Blue Cross Blue Shield of Illinois to replace the Target store that closed in February, creating an uproar.
  • R2019-690 — An endorsement of a tax break that would allow a new 12,000-square-foot warehouse to replace an obsolete facility at 4207 W. Ogden Ave.
  • R2019-693 — An endorsement of a tax break for Aero Chicago on the new 276,000-square-foot cargo facility the firm built at O’Hare International Airport.
  • O2019-1383 — A proposal from Sterling Bay for an 18-story tower at 1000 W. Carroll Ave. and an 11-story complex across the street at 345 North Morgan St.
  • O2019-4344 — A proposal by Carroll Avenue Associates to convert the industrial building at 1234 W. Fulton Market in the 27th Ward into a 14,000-square-foot office space.
  • O2019-6934 — A proposal to require new parking garages and most new multi-unit residential buildings to include charging stations for electric vehicles.
  • O2019-6829 — Plans to convert a 161-unit single-room occupancy hotel at 1039 W. Lawrence Ave. into an 80-unit apartment complex with shops on the ground floor.
  • O2019-6812 — Plans for a four-story, 24-unit apartment complex at 5100 N. Western Ave. in the 40th Ward.
  • O2019-6034 — Plans to add 25 units to the transitional housing center at 1223 W. Marquette Road and convert it to permanent supportive housing.
  • O2019-6915 — A measure to allow more than four members of the Commission on Chicago Landmarks to be replaced in a one-year period.
  • The settlement of three police misconduct cases for $5.4 million. [Our coverage]
  • 11 property sales [Our coverage]
  • 5 measures governing the sale of packaged liquor [Our coverage]
  • A2019-67 — The appointment of Angela Hurlock as chair of the [Hurlock sails through confirmation hearing to lead CHA board]
  • A2019-68 — The appointment of Frank J. Lindbloom as member of Chicago Emergency Telephone System Board.
  • A2019-72 — The appointment of Tiara L. Hughes to the Commission on Chicago Landmarks.
  • A2019-71 — The appointment of Paola Aguirre Serrano to the Commission on Chicago Landmarks.
  • A2019-63 — The appointment of Guacolda E. Reyes as member of the Plan Commission.