Free Tip and the Gipper: When Politics Worked by Chris Matthews Page A

fit into the pecking order of the O’Neill office, and how each interacted with Tip and with one other. It was critical to know what to expect before I took my place alongside the Speaker’s team—which, like Reagan’s, was a small, tight group.
    What I learned is how much Tip relied on his closest aides when it came to the business of keeping Congress functioning. It was because these men had the Speaker’s ear that other House members treated them with such respect and attention.
    Here are the most important members of Tip’s trusted associates, the ones I got the skinny on before meeting them. First, there was Kirk O’Donnell, chief counsel to the Speaker, who’d been, before he came to work for Tip, a highly effective top aide to Boston mayor Kevin White. It was Tip’s son Christopher (known as “Kip”) who’d encouraged his father to bring O’Donnell on board, looking to add to the staff the kind of political street smarts Kirk had in full. Kip also had wanted a skilled player who’d be able to see both the big and little picture. Most vitally, the son was looking for a person who’d protect his dad. Kirk had turned out to be a brilliant hire, going on to win the Speaker’s highest accolade. He’s “hard as a rock,” Tip O’Neill would say of him approvingly. What impressed me, once I got to know him, was how fearless Kirk was, so absolutely sure of his position. Tip had to beg him to take the job. And Kirk was always willing to take on anyone who dared to confronthim. That said, though, his reputation was always that of “a good guy” to have a beer with.
    O’Donnell, I soon learned, was working in cahoots with Congressman Coelho when it came to bringing me in. Both believed the Speaker was poised to become a national figure far larger than any previous Capitol Hill leader. I should add that Kirk, older than his own years, was steeped in the ways of the bygone political world of Boston. Over the time we spent together he worked carefully to educate me with regard to the lore he held so dear, above all those political rules and maxims that had guided the previous generations. Most important, he made it very clear that there are rules and that they exist for good reason.
    Gary Hymel, the Speaker’s administrative assistant, was the most visible of O’Neill’s top aides. His large desk, in the room right off the House chamber, adjoined the Speaker’s ceremonial office, making him the front gatekeeper. A former newspaperman from New Orleans, he’d been a top aide for House majority leader Hale Boggs of Louisiana. Then, when the twin-engine plane carrying Boggs was tragically lost over Alaska in 1972, Gary, with the agreement of the Boggs family, helped Tip, who’d been majority whip, to win election to become majority leader. In addition to handling the press, Gary was the Speaker’s key liaison with southern members. Observing him in action, I could tell he was an extremely popular guy around the House.
    Leo Diehl, who held the same highest-ranking title as Hymel, “Administrative Assistant,” was another quintessential political operator. Elected to the Massachusetts legislature from an adjoining district in 1936, the same year as O’Neill, the two quickly became friends for life. Leo, who’d been crippled by polio as a boy, relied on crutches, refusing ever to resort to a wheelchair. He and Tip would, without the slightest embarrassment, sing old neighborhoodsongs—“Paddy McGinty’s Goat” and“Nobody Knows What Happened to McCarty”—on their way down those great corridors at night. Leo’s desk was in the little anteroom to Tip’s working office, hidden along the Capitol’s East Front. From this well-placed spot he was entrusted by Tip to decide which lobbyists to let through the door, whom to hit up at fund-raising time, and what scores warranted settling. Leo and Millie O’Neill were the only ones who called the Speaker “Tom.”
    Ari Weiss, Tip’s legislative whiz kid,