In 2000, after Goldman Sachs went public, Ryan's net worth was in the hundreds of millions. He retired from Goldman and taught part-time at an inner-city Chicago Catholic parochial school, Hales Franciscan High School. He later became a full-time teacher at the school. Currently, Mr. Ryan is running a news media company, 22nd Century Media, which publishes five separate localized newspapers in the greater Chicago area.
Controversially, in 2004, Ryan had Justin Warfel (a campaign worker) follow his opponent, Barack Obama, throughout the day and record everything he did in public on videotape. The tactic backfired when many people, including Ryan's supporters, criticized this activity. Ryan's spokesman apologized, and promised that Warfel would give Obama more space. Obama acknowledged that it is standard practice to film an opponent in public, and Obama said he was satisfied with Ryan's decision to have Warfel back off.
People alleged to be Barack Obama's backers emailed reporters about the divorce controversy, but refrained from on-the-record commentary about the divorce files. On March 29, 2004, Los Angeles Superior Court Judge Robert Schnider ruled that several of the Ryans' divorce records should be opened to the public, and ruled that a court-appointed referee would later decide which custody files should remain sealed to protect the interests of Ryan's young child. The following week, on April 2, 2004, Barack Obama changed his position about the Ryans' soon-to-be-released divorce records, and called on Democrats to not inject them into the campaign. The Ryan campaign characterized Obama's shift as hypocritical, because Obama's alleged backers had been emailing reports about the divorce records prior to Judge Schnider's decision.
On June 22, 2004, after receiving a report from the referee, Judge Schnider released the files that were deemed consistent with the interests of Ryan's young child. In those files, Jeri Ryan alleged that Jack Ryan had taken her to sex clubs in several cities, intending for them to have sex in public. The decision to release these files generated much controversy because it went against both parents' direct request, and because it reversed the earlier decision to seal the papers in the best interest of the child. Jim Oberweis, Ryan's defeated GOP opponent, commented that "these are allegations made in a divorce hearing, and we all know people tend to say things that aren't necessarily true in divorce proceedings when there is money involved and custody of children involved."
Prior to release of the documents, Ryan claimed he had told leading Republicans that the divorce file could cause problems for his campaign. But after the documents were released, GOP officials including state GOP Chair Judy Baar Topinka said they felt Ryan had mislead them, saying the divorce records would not be embarrassing. That charge of dishonesty led to calls for Ryan's withdrawal, though Topinka said after the June 25 withdrawal that Ryan's "decision was a personal one" and that the state GOP had not pressured Ryan to drop out. Ryan's campaign ended less than a week after the custody records were opened, and Ryan officially filed the documentation to withdraw on July 29, 2004. The same party leaders who called for Ryan's resignation chose Alan Keyes as Ryan's replacement in the race; Keyes lost to Obama, 27% to 70%.