It was the day no one thought they would see happen—at least in this lifetime. On Nov. 2, the eternal underdogs the Chicago Cubs won the 2016 World Series Championship, ending a 108-year wait and gaining a whole lot of new appreciation and fans as a result. Just 10 weeks later they would celebrate yet again at the annual fan convention at the Sheraton Grand Chicago, which was an undeniable success thanks to the quick actions of a team of event producers.
“This year was a really tight window for finalizing the planning,” says Jim Oboikowitch, manager of game and event production. Though he and his staff of three are in constant contact with the hotel throughout the year, piecing together the minutia of player schedules and the general itinerary happens after the season ends, normally in late September or October. “It was a stretch meeting deadlines for printed materials and trying to be cognizant of not bothering people during the holiday season,” he furthers, “but in the end it worked out well.”
The uniqueness of this year’s convention (the 32nd edition) was not lost on Oboikowitch and his team who “went back to the drawing board” after the monumental win to ensure every detail was considered, especially given the intense demand.
“We had to rethink some things,” he admits. “We want fans to have a great time, but we worry about congestion. We don’t want fans waiting in line forever.”
The event is one of the hottest sporting events in town, offering an opening night ceremony with the entire team, a late night “talk show” with former pitcher Ryan Dempster and numerous Q&A panels and autograph sessions throughout a three-day weekend. This year, like most, the 10,000 available tickets sold out “within a matter of minutes.”
To help with the flow of people, the event team decided to open up registration lines early in the morning, add a couple more stages for autograph signings and introduce several more dining spots—all catered by the hotel—so attendees could sit and relax throughout the day.
Since moving the convention to the Sheraton from the Hilton Chicago a few years ago, there is also access to one of the city’s largest ballrooms, which is an important component since the opening night festivities and most of the Q&As take place here. “This year we decided to move the air walls even more in the ballroom to allow 3,000 fans to be able to sit and enjoy the panels and have the chance to ask questions,” says Oboikowitch.
One of the most impressive new features, though, was having the World Series trophy as a guest of honor. “We created a tent just outside the convention doors on Lower Wacker Drive, so it never felt like you were outside because it was all contained,” says Oboikowitch. It’s an important point since the event was held in the middle of January. The staff also opted to extend the hours for viewing and photo opportunities, leaving it on display until 10 p.m. the first two nights.
Of course with all the attention given to the team and the trophy, security was top of mind.
“We always make sure our players are taken care of and always have security with them to lead them to different areas, so they don’t get lost and we know they’ll be on time for their next scheduled appearance,” says Oboikowitch. “But one thing we changed this year was to work with the hotel so that guests that didn’t have a regular reservation or hadn’t purchased convention passes were not inside the property.” That included the main lobby area, which is normally a gathering area for the public.
In years past we’ve had people trying to sneak in, which just adds to the congestion and is a risk, so we wanted to eliminate that. We would have done that whether we won the World Series or not, but it was definitely an emphasis this year.” To that point, Cubs personnel sent a number of reminders to ticket holders to wear their badges, which had unique holograms on the front to designate that they were official and to make it easier on the on-site security checking passes at various entry points.
To accomplish all the various technical details, the Cubs partnered with PSAV for audio-visual needs, which included lighting for Dempster’s talk show and microphones for all the panels. “We wanted to enhance some of those features this year, and they really stepped it up for us,” says Oboikowitch, noting that the kids-only press conference was one of the weekend’s highlights. “You always get a lot of off-the-cuff questions, like who’s your favorite superhero or your favorite cereal.”
After the convention wrapped, the Cubs staff distributed surveys to attendees asking for feedback. “There are always a few things we change every year. We always want to make it easier on fans and hope they have a great experience,” notes Oboikowitch of the convention, which he sees as a fun way to bridge the gap from the off-season and lead into spring training. “It’s a great way for fans to see players during the winter and get people thinking about baseball once again.”
