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Sign Company’s Pickleball Game Turns Sour

When misfortune strikes, the shop owner is faced with a potentially costly dilemma. Your peers offer solutions in “The Case of the Ill Pickle.”




“I GOT IT!” Chris shouted as he saw his opponent execute a drop shot. Using the quick and agile skills that served him so well in the fabrication department of City Sign Co. in Manchester, NH, he sprang forward, already preparing a cross-court passing shot right across United Printworks’ kitchen…

“Let’s join this pickleball league,” Dani had brought up at a weekly meeting, three months before. “It’s a lot of fun and at least four or five of us know how to play.” The local parks department had announced the league and several companies were already entering teams, including rival United Printerworks, and clients Arsenal Heating & Cooling and Chelsea Plumbing, both of whom City Sign had done fleet designs and installations for.


Real Deal scenarios are inspired by true stories, but are changed to sharpen the dilemmas involved and should not be confused with real people or places. Responses are peer-sourced opinions and are NOT a substitute for professional legal advice. Please contact your attorney if you any questions about an employee or customer situation in your own business.


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“We want to represent Ci-ty and show everyone who’s got the best pickleballers … and sign installers,” Dani continued and everyone laughed, as she was City’s lead installer.

“I don’t know; what do you all think?” City Sign Co. owner Jamie asked the group of 17 employees sitting and standing around the company’s conference room table…

Dani felt certain Chris would reach the dropshot. Of the two teams City Sign had entered into the pickleball league, the team of Dani and Chris had dominated the first four weeks’ worth of opposition. United Printworks carried a very respectable 3-1 record into matchweek five. Were United to prevail, both teams would share 4-1 results, but the head-to-head win would put up top of the table. But were City to win, they would move to 5-0, knocking United into third or even fourth place, depending on the outcomes of other games.

Between them, Dani and Chris could chop, dink, punch, slice or smash as needed. In the best of three games against United, City had already won the first and UP were serving in the second at 4-5, trying to stay alive…


Jamie had authorized the check to cover the league fee for the company’s two teams, Hector and Luna comprising “Team B” as they both joked, knowing they were in it just for the fun. Jamie noticed that the participants would have to sign a waiver, releasing the Parks Department from all liability. She wondered about that for a few moments, but as the games were to be played off premises and off hours — and looked low-impact — she concluded no further coverage seemed merited.

In the weeks leading up to the match against UP, the two companies exchanged some (mostly) good-natured barbs across social media. City’s design and marketing team proved the difference with their “bread and butter pickle” series on Instagram…

The drop shot landed softer than Chris had anticipated. He summoned every reserve to make up the distance. And he would have, had he kept his balance.

Dani watched as time seemed to compress: Trying to brace his fall, Chris landed awkwardly first on his thumb, badly dislocating it. Lacking that brace, he then planted his face on his side’s “kitchen floor,” breaking his jaw and orbital bone, and leaving three cracked teeth behind…

Jamie met Dani at the emergency room, where Chris had been brought by ambulance. He would require a series of surgeries including dental reconstruction. Doing her best to stay strong for Dani, who was understandably still very upset — “I don’t think I’ll ever be able to get that image out of my mind,” she said — Jamie’s mind was also racing.

The company’s insurance was good, but as a shop of only 18 all together, City Sign lacked buying power, so many of the young, healthy employees like Chris had chosen the high-deductible plan. Without question, Jamie knew Chris was looking at major expenses and time for the necessary care and rehabilitation from this horrific accident.


The Big Questions

  • What — if anything — should Jamie and City Sign Co. do for Chris? Offer to help with some of the costs? Or would that be tantamount to accepting responsibility?
  • What about his job, which he would not be able to perform for months, at the very least?
Nichole L.
Morrisville, VT

Business owners must take care of their employees if they expect their employees to take care of them. Although Jamie may not be legally obligated to shoulder the employee’s bills, she should do it because it’s the right thing to do. Ask the employee to run his bills through insurance, and then quietly, on the side, pay the deductible and additionals (like transportation, etc.) out of her own pocket. If it makes it easier to [give a bonus to] the employee in order to make that happen, so be it. Sometimes we need to get creative but the end goal is taking care of your people. After all, the employee never would have been there if it weren’t for his employment at her company.

Heather W.
Findlay, OH

This is covered under Workers’ Comp (at least it is in Ohio). The employee was participating in a company-sanctioned event and although it was voluntary, he was injured in the event. The company can check with their Workers’ Comp insurance provider for details, but the employee’s medical expenses and wages would be taken care of while under medical care. I know this from personal experience — a person was injured during a softball game and was playing for their spouse’s company. They could not work and required surgery and it was all covered under the spouse’s employer’s workers’ comp coverage.

Laura B.

Outfront, Tampa, FL

Set up a GoFundMe page.

Jasper B.
Conway AR

A tough one! I would push my insurance company to cover my employee. At the very least, I would talk to my agent before participating and make a determination of coverage. Often insurance companies dictate how we should run our businesses, but of course, it’s for our own protection, so we should be thankful. Most of the time, my agent brags about the high quality of coverage during the quote presentation. That is the person I call beforehand. Most of the time, we would be covered, but I would get confirmation prior to the first serve.

Guy C.

City should start a GoFundMe page and contribute. Let others starting with the pickleball league members know about Chris, his injuries and expenses and encourage them to match City’s donation, and if they can’t match, contribute something. Use social media to get the word out about the GFM page and also use local media to spread the word. In this way, concerns about liability and Chris’ future could be shared, minimized or eliminated.

Lisa Y.
Springfield, MA

Yes, there should be some assistance provided and of course back to work with those allowances! It takes a team effort in work and play!




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