This story was produced with the Better Government Association, a Chicago nonprofit newsroom focused on government accountability.

The coronavirus pandemic paralyzed Mark Aistrope’s company renting out technology for business conferences. 

Then, he saw an opportunity: His company was sitting on a large fleet of laptops and iPads just as the Chicago school district needed thousands of devices after the outbreak abruptly shifted learning online.

Aistrope, the CEO of Chicago-based Meeting Tomorrow and a campaign contributor to Mayor Lori Lightfoot, reached out to her office in late March. The next day, he said, he was on a video call with top Chicago school district officials — the first step before sealing a more than $1.6 million deal to buy used laptops and older-model iPads from Aistrope’s firm.

Like school districts across Illinois and the nation, Chicago set out to rapidly build up its technology arsenal under extremely trying circumstances. It ran into major supply issues, entrenched disparities in broadband access in the city, and an aging pre-pandemic fleet of devices. At a price of $30 million through July, Chicago’s push to get technology to students was a herculean lift; the district largely leaned on long-time suppliers and got reasonable prices.

But an analysis by Chalkbeat Chicago and the Better Government Association of spring and summer purchase orders as well as interviews with technology experts, district leaders, and families also shows the district placed some device orders later than other large Illinois districts, left some families grappling with slower or malfunctioning devices from its stock and, in the case of the Meeting Tomorrow purchase, settled for buying used, older devices.

Thrust almost overnight into the role of technology hubs, Chicago and other school districts across the state now face ongoing costs and responsibilities — from repairing damaged machines to training teachers — at a time when the country appears poised for extreme financial uncertainty. How they confront the task presents a major new test as Chromebooks and iPads have become as essential school supplies in 2020 as textbooks, a comparison recently made by Chicago schools chief Janice Jackson.

“The way we manage IT in school districts still isn’t particularly mature,” said Douglas Levin, president of EdTech Strategies, which consults with school districts. “When we have money, we’ll go out and buy the tools we want. But districts can be under-resourced to manage these purchases.”

Chicago school leaders say they are proud of the district’s response to the pandemic — and are prepared for an all-virtual start to the coming school year.

“COVID-19 really created nothing short of a perfect storm for us,” said Phillip DiBartolo, Chicago’s chief information officer, adding, “At the end of the day, I was perfectly satisfied with the effort and level of coordination.”

‘No stone unturned’

While Chicago ran up against major demand for devices last spring, the district was able to turn to two heavy hitters with whom it had signed multimillion-dollar contracts and forged relationships in recent years: Apple and CDW-G, which is Chicago’s middleman for Dell laptops and Chromebooks.

“They moved heaven and earth to make sure that CPS got what we needed as quickly as they possibly could have on a constrained supply chain to make sure that our students could engage in remote learning,” said DiBartolo.

Those two vendors got the bulk of Chicago’s business in the spring, with about $13.6 million going to CDW-G and $5.8 million to Apple. Overall, the district scored good deals on tablets and laptops, several education technology experts agreed. 

But the district also turned to a third company, which it had never worked with before: Aistrope’s Meeting Tomorrow. The company, which before the pandemic loaned out equipment for conferences and other large events, sold the district an assortment of used devices: two- and three-year-old iPads, an iPad Air model discontinued three years ago, as well as Lenovo ThinkPads and Dell laptops.

The district didn’t get deep discounts. For instance, it paid $300 for the 2017 iPads, slightly more than what the district paid Apple for brand-new devices. The older iPads came with cell service capacity, but they’re not worth the higher cost without a data plan, experts said.

Some experts also said a mishmash of devices and models complicates maintenance and software choices. The older-model machines are closer to the end of their life cycles and less likely to run up-to-date software, while some of the laptops came with more limited memory and might require a memory upgrade down the road.

“Our approach was leave no stone unturned and talk to anyone that had reasonable product at a reasonable price.” Phillip DiBartolo, Chicago Public Schools

“Why would they buy older, slower machines?” asked Richard Culatta of the nonprofit International Society for Technology in Education. “There would need to be some logical reason for that decision; otherwise, I would expect to see the newest models and not so many different models.”

But another expert, Hal Friedlander, head of the nonprofit Technology for Education Consortium and a former chief information officer of New York City Public Schools, said the older machines should meet students’ needs, and that the arrangement looks like an out-of-the-box way to get around supply difficulties.

In an interview, DiBartolo wouldn’t discuss the deal with Meeting Tomorrow — the district’s fourth-largest tech vendor last spring — saying he and his staff spoke with a “litany” of vendors soliciting district business.

“Our approach was leave no stone unturned and talk to anyone that had reasonable product at a reasonable price,” DiBartolo said.

The district did not provide a contract with the company or responses to a list of questions about the purchase.

But in an interview, Aistrope said after learning the district needed technology, he contacted Samir Mayekar, Chicago’s deputy mayor for economic and neighborhood development. Aistrope said he met Mayekar last fall when he reached out about getting involved in the city’s Invest South/West initiative, a public-private partnership aimed at revitalizing historically disinvested parts of Chicago. 

Mayekar forwarded Aistrope’s inquiry to Sybil Madison, deputy mayor for education, who sent it to the school district. The following day, Aistrope said he was on a Zoom conference call, pitching his company’s devices to DiBartolo and the district’s chief operating officer, Arnaldo Rivera.

He said the devices sold to the district, which he believes went to charter schools, were in “excellent condition” and the company charged reasonable prices in “a nutty, crazy market.” The purchase also kept the company afloat at a time when it faced layoffs; Aistrope said renting and selling devices to school districts and college campuses now makes up the bulk of his business.

“Why would they buy older, slower machines? There would need to be some logical reason for that decision.” Richard Culatta, International Society for Technology in Education

In 2019, Aistrope contributed nearly $30,000 in cash and in-kind contributions for Lightfoot’s mayoral bid, campaign records show. He acknowledged it might appear as though his contribution helped secure the deal with the district, but said that wasn’t the case.

“Obviously I can see how somebody might say that, not having the context,” he said. “It’s not my intent and if I ever thought that this would kind of muddy anything, I wouldn’t have done it.”

He added that when he made the contributions to Lightfoot’s campaign he never intended to do business with the city.

“We did this to help out,” he said. 

Mayekar said he only spoke with Aistrope once — about Invest South/West — prior to Aistrope’s inquiry this spring and said he was not aware Aistrope contributed to Lightfoot’s campaign.

“I connect people and constituents who reach out to our office to really help them make the connections that they need regardless of who reaches out to us,” Mayekar said. “When he offered assistance at a time of need, just like many people do every week, I put him in touch with the people looking for goods and services and donations.” 

A first round of orders, then a second

Chicago placed large device orders during the first week of April. Late that month, after the district learned the need for devices was greater than expected, it bought thousands of additional computers, including the devices from Meeting Tomorrow. 

DiBartolo said its suppliers rushed the machines to the district. Most of the more than 50,000 computers it bought took six to eight weeks to arrive, getting in during the second half of April and first half of May, “with some straggling in after that” — a timeline that meant some students received their district-issued devices just weeks before the school year’s mid-June end. 

Some other Illinois districts moved faster.

Elgin, a 37,400-student district in Chicago’s northwest suburbs, put in an order for nearly 4,000 Chromebooks on March 17, the day schools in Illinois closed. Rockford, a district with 28,200 students in northern Illinois, had enough devices on hand to cover students who needed computers. But on April 3, it bought 18,450 new iPads and Chromebooks so it could retire older devices and replace some it had been leasing. Both districts got their deliveries in four weeks.

In Chicago, DiBartolo said the district didn’t need to wait on its orders: It started giving out its existing stock of about 65,000 devices, some of which were acquired as part of the district’s 2024 goal to provide a computer to each of the district’s 300,000 students. At the local level, said Elaine Allensworth of the Consortium on Chicago School Research, schools placed differing values on acquiring computers in the years before the pandemic and have ended up with uneven device stocks, with some campuses investing in technology while others lagged behind.

Some students and parents say the older computers Chicago handed out were not well-suited to virtual learning, in part, because of the wear and tear from students who had previously used them.

Students said the slow speed of older Chromebooks made it hard to livestream video classes and upload assignments. One parent said that two of the four school-issued devices had malfunctioning cameras and microphones, while another said the keyboard was broken.

Esmeralda DeLaGarza, a sophomore at Solorio Academy High School on the city’s Southwest Side, received a 2012 model Chromebook from her school. She said she could only watch video classes from her cell phone and could keep only one tab open at a time on the Chromebook. 

“Many students at my school were saying these devices were trash,” DeLaGarza said. “I thought I was lucky to have a device at all.”

The district launched a new parent help desk to assist families with the abrupt transition to remote learning. Tracy Occomy Crowder, deputy director of the parent advocacy group Community Organizing and Family Issues, said families across the state struggled to navigate technology issues. They were sometimes unsure where to turn for help — the district’s help desk or their schools — and craved more guidance on how to help their kids make the most out of learning online.

“Folks have risen to the occasion, but it shouldn’t be all on them,” she said. 

DiBartolo said the district’s pre-pandemic device stock was “perfectly serviceable for the need,” but the district is reaching out to students who received devices that were “a little bit longer in the tooth” about replacing them ahead of the school year’s start.

“I was very proud of our principals for rising above and doing everything they could and more to make sure that our students had the requisite degree of equipment at home,” he said.

The remote learning transition challenged technology teams in many districts, including some that had more extensive technology stockpiles than Chicago.

Before the pandemic, Springfield was already close to its goal of having a device for each of its roughly 13,000 students. But it hadn’t yet invested in an online learning management platform. After the shift to remote learning, parents and students were suddenly receiving emails and messages across multiple platforms and from different teachers throughout the school day, Jennifer Gill, Springfield’s superintendent, said.

The district paid $72,000 to roll out a platform called Canvas, which allows teachers to set up remote classrooms. The use of the program wasn’t mandatory in the spring, but some experts said it would be an extremely challenging transition amid the pandemic. Springfield Education Association President Aaron Graves said many teachers who are less technologically savvy have struggled.

“As they’re trying to figure this out, it puts a lot of stress onto them,” he said.

Looming costs

Buying devices and accessories at the height of the pandemic is only a first step — an initial crack at addressing profound technology access gaps rather than a permanent solution.

In Chicago, the teachers union and others criticized the school district for lagging on a comprehensive plan to address internet access gaps until the city unveiled an initiative to provide free internet to 100,000 students after the school year’s end.

“In March, everyone rushed out to buy devices and get them to kids. We were all completely surprised. Now we know. So how are districts adapting?” Hal Friedlander, Technology for Education Consortium

DiBartolo said Chicago, which bought 12,000 additional Chromebooks and 4,000 iPads in July, is heading into the fall in a strong position. The district offered digital learning training for teachers over the summer and recently announced a $1.5 million donation from Boeing to buy computers and headsets for students and teachers. Any student who needs a computer this fall will get one, the district has vowed.

Experts say districts should be hard at work making strategic plans for their drastically expanded device fleets. They need to put thought and money into maintaining and repairing computers, training educators, selecting high-quality digital content, and more. 

“In March, everyone rushed out to buy devices and get them to kids,” said Friedlander. “We were all completely surprised. Now we know. So how are districts adapting?”

That sort of long-range planning may prove difficult as supply issues for technology continue unabated.

Complicating matters for Chicago and other districts are looming financial pressures wrought by the pandemic. Many district officials in Illinois counted on an initial federal stimulus package approved last spring to recoup their spending on technology, but they don’t have a source for the ongoing costs of ownership.

Chicago is counting on a second federal stimulus infusion of $343 million to balance its 2020-2021 budget, but talks about the package in Congress have stalled. Meanwhile, a recent bid by Illinois to rectify historic underfunding of its schools was upended by the pandemic, leaving districts’ funding flat for the coming year.

Rockford is charting out a multi-year plan to save for another big round of spending when the devices it purchased this year need to be replaced. The plan doesn’t count on more relief from the federal government, but will rely in part on an increase in state funding in future years. 

Maintenance and replacement costs will present a challenge for districts across the state. 

“The fear is, when these Streams get old, then what?” said Carla Eman, director of budgets and compliance for Peoria Public Schools, referring to the HP version of a Chromebook the district placed a large order for in June. “I don’t know. We’ll just have to figure it out as the time goes by.”

Sam Park at Chalkbeat Chicago contributed to this report.